Skills Iit Jee Chemistry

8/4/2019 Skills Iit Jee Chemistry

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Physical & General Chemistry

General Chemistry Done

1 Apply the law of the conservation of mass.2 Compare and contrast the three common states of matter: solid, liquid, and gas.

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Describe the classifications of matter: elements, compounds, and mixtures

(heterogeneous and homogeneous).

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Understand the difference between chemical changes (chemical reactions) and physical

changes.5 Distinguish between chemical properties and physical properties.6 Become familiar with the SI (metric) system of units, including the SI prefixes.7 Convert from one temperature scale to another.8 Calculate the density of a substance.9 Use density to relate mass and volume.10

Apply dimensional analysis to solving numerical problems.11 Convert from one metric unit to another metric unit.12 Convert from one metric volume to another metric volume.13 Convert from any unit to another unit.

Atoms, Molecules, and Ions14 Describe Thomsons experiment in which he discovered the electron.15 Describe Rutherfords experiment that led to the nuclear model of the atom.16 Write the nuclide symbol for a given nuclide.17 Define and provide examples ofisotopes of an element.18 Write the nuclide symbol of an element.

Determine the atomic mass of an element from the isotopic masses and fractional

843 things you should know to secure top 100 Rank in IIT -JEE

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a un ances.20 Determine when the chemical formula of a compound represents a molecule.21 Determine whether a chemical formula is also a molecular formula.22 Define ion, cation, and anion.23 Classify compounds as ionic or molecular.24 Define and provide examples for the termformula unit.25 Specify the charge on all substances, ionic and molecular.26 Write an ionic formula, given the ions.

27 Learn the rules for predicting the charges ofmonatomic ions in ionic compounds.

28 Apply the rules for naming monatomic ions.29 Learn the names and charges of common olyatomic ions.30 Name an ionic compound from its formula.

31 Write the formula of an ionic compound from its name.32 Determine the order of elements in a binary (molecular) compound.

33Learn the rules for naming binary molecular compounds, including the Greek prefixes.

34 Name a binary compound from its formula.35 Write the formula of a binary compound from its name.36 Name a binary molecular compound from its molecular model.37 Recognize molecular compounds that are acids.38 Determine whether an acid is an oxoacid.39 Learn the approach for naming binary acids and oxoacids.40 Write the name and formula of an anion from the acid.41

Recognize compounds that are hydrates.42 Learn the rules for naming hydrates.43 Name a hydrate from its formula.44 Write the formula of a hydrate from its name.

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45

Write chemical equations using appropriate phase labels, symbols of reaction

conditions, and the presence of a catalyst.46 Determine if a chemical reaction is balanced.47 Master the techniques for balancing chemical equations.

Calculations with Chemical Formulas and Equations48 Calculate the formula mass from a formula.49 Calculate the formula mass from molecular models.50 Define the quantity called the mole.51 Learn vogadros number.52 Understand how the molar mass is related to the formula mass of a substance.53 Calculate the mass of atoms and molecules.54 Perform calculations using the mole.55 Convert from moles of substance to grams of substance.56 Convert from grams of substance to moles of substance.57 Calculate the number of molecules in a given mass of substance.58 Define mass percentage.59 Calculate the percentage composition of the elements in a compound.60 Calculate the mass of an element in a given mass of compound.

61 Describe how C, H, and O combustion analysis is performed.62 Calculate the percentage of C, H, and O from combustion data.63 Define empirical formula.

64

Determine the empirical formula of a binary compound from the masses of its

elements.65 Determine the empirical formula from the percentage composition.

66

Understand the relationship between the molecular mass of a substance and its

empirical formula mass.

67

Determine the molecular formula from the percentage composition and molecular

mass.

Relate the coefficients in a balanced chemical equation to the number of molecules or

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68 moles (molar interpretation ).69 Use the coefficients in a chemical reaction to perform calculations.70 Relate the quantities of reactant to the quantity of product.71 Relate the quantities of two reactants or two products.

72

Understand how a limiting reactant or limiting reagent determines the moles of

product formed during a chemical reaction and how much excess reactant remains.

73 Calculate with a limiting reactant involving moles.74 Calculate with a limiting reactant involving masses.75 Define and calculate the theoretical yield of chemical reactions.76 Determine the ercentage yield of a chemical reaction.

77

From the molecular equation of both strong electrolytes and weak electrolytes,

determine the complete ionic equation.78 From the complete ionic equation, write the net ionic equation.79 Write net ionic equations.80 Recognize recipitation (exchange ) reactions.

81Write molecular, complete ionic, and net ionic equations for precipitation reactions.

82 Decide whether a precipitation reaction will occur.83 Determine the product of a precipitation reaction.

84

Understand how an acidbase indicator is used to determine whether a solution is

acidic or basic.85 DefineArrhenius acid andArrhenius base.86 Write the chemical equation of an Arrhenius base in aqueous solution.87 DefineBrnstedLowry acid andBrnstedLowry base.88 Write the chemical equation of a BrnstedLowry base in aqueous solution.

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89Write the chemical equation of an acid in aqueous solution using a hydronium ion.

90 Learn the common strong acids and strong bases.91 Distinguish between a strong acid and a weak acid and the solutions they form.

92Distinguish between a strong base and a weak base and the solutions they form.

93 Classify acids and bases as strong or weak.

94 Recognize neutralization reactions.95 Write an equation for a neutralization reaction.96 Write the reactions for apolyprotic acid in aqueous solution.97 Recognize acidbase reactions that lead to gas formation.98 Write an equation for a reaction with gas formation.99 Define oxidationreduction reaction.100 Learn the oxidation-number rules.101 Assign oxidation numbers.102 Write the half-reactions of an oxidationreduction reaction.103 Determine the species undergoing oxidation and reduction.

104

Recognize combination reactions, decomposition reactions, displacement

reactions, and combustion reactions.105 Use the activity series to predict when displacement reactions will occur.106 Balance simple oxidationreduction reactions by the half-reaction method.107 Define molarity or molar concentration of a solution.108 Calculate the molarity from mass and volume.109 Use molarity as a conversion factor.110 Describe what happens to the concentration of a solution when it is diluted.111 Perform calculations associated with dilution.112 Diluting a solution.113 Determine the amount of a species bygravimetric analysis.114 Calculate the volume of reactant solution needed to perform a reaction.

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115 n erstan ow to per orm a t trat on .116 Calculate the quantity of substance in a titrated solution.

The Gaseous State117 Definepressure and its units.118 Convert units of pressure.119 ExpressBoyles law in words and as an equation.120 Use Boyles law.121 Express Charless law in words and as an equation.122 Use Charless law.123 Express the combined gas law as an equation.124 Use the combined gas law.125 State vogadros law.

126 Define standard temperature and pressure (STP).127 State what makes a gas an ideal gas.128 Learn the ideal gas law equation.129 Derive the empirical gas laws from the ideal gas law.130 Use the ideal gas law.131 Calculate gas density.132 Determine the molecular mass of a vapor.133 Use an equation to calculate gas density.134 Solving stoichiometry problems involving gas volumes.135 Learn the equation for Daltons law of partial pressures.136 Define the mole fraction of a gas.137 Calculate the partial pressure and mole fractions of a gas in a mixture.

138

Describe how gases are collected over water and how to determine the vapor pressure

of water.139 Calculate the amount of gas collected over water.

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140 List the five postulates of the kinetic theory.141 Provide a qualitative description of the gas laws based on the kinetic theory.

142

Describe how the root-mean-square (rms) molecular speed of gas molecules varies with

temperature.

143Describe the molecular-speed distribution of gas molecules at different temperatures.

144 Calculate the rms speed of gas molecules.145 Define effusion and diffusion.146 Describe how individual gas molecules move undergoing diffusion.147 Calculate the ratio of effusion rates of gases.148 Explain how and why a real gas is different from an ideal gas.149 Use the van der Waals equation.

Quantum Theory of the Atom150 Define the wavelength andfrequency of a wave.151 Relate the wavelength, frequency, and speed of light.152 Describe the different regions of the electromagnetic spectrum.153 State Plancks quantization of vibrational energy.154 Define Plancks constant and hoton.

155 Describe the photoelectric effect.156 Calculate the energy of a photon from its frequency or wavelength.157 State the postulates of Bohrs theory of the hydrogen atom.158 Relate the energy of a photon to the associated energy levels of an atom.159 Determine the wavelength or frequency of a hydrogen atom transition.160 Describe the difference between emission and absorption of light by an atom.161 State the de Broglie relation.162 Calculate the wavelength of a moving particle.163 Define quantum mechanics.164 State Heisenbergs uncertainty principle.

Relate the wave function for an electron to the probability of finding it at a location in

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165 space.166 Define atomic orbital.167 Define each of the quantum numbers for an atomic orbital.168 State the rules for the allowed values for each quantum number.169 Apply the rules for quantum numbers.170 Describe the shapes of s, p, and d orbitals.

Electron Configurations and Periodicity171 Define electron configuration and orbital diagram.172 State the Pauli exclusion principle.173 Apply the Pauli exclusion principle.174 Define building-up principle.175 Define noble-gas core, pseudo-noble-gas core, and valence electron.

176 Define main-group element and (d-block and f-block) transition element.177 Determine the configuration of an atom using the building-up principle.178 Determine the configuration of an atom using the period and group numbers.179 State Hunds rule.180 Apply Hunds rule.181 Defineparamagnetic substance and diamagnetic substance.182 Describe how Mendeleev predicted the properties of undiscovered elements.183 State the periodic law.184 State the general periodic trends in size of atomic radii.185 Define effective nuclear charge.186 Determine relative atomic sizes from periodic trends.187 State the general periodic trends in ionization energy.188 Definefirst ionization energy.189 Determine relative ionization energies from periodic trends.190 Define electron affinity.

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191 State the broad general trend in electron affinity across any period.192 Define basic oxide, acidic oxide, and amphoteric oxide.

193

State the main group corresponding to an alkali metal, an alkaline earth metal, a

chalcogen, a halogen, and a noble gas.

194

Describe the change in metallic/nonmetallic character (or reactivities) in going through

any main group of elements.

Ionic and Covalent Bonding195 Define ionic bond.196 Explain the Lewis electron-dot symbol of an atom.197 Use Lewis symbols to represent ionic bond formation.198 Describe the energetics of ionic bonding.199 Define lattice energy.

200Describe the BornHaber cycle to obtain a lattice energy from thermodynamic data.

201 Describe some general properties of ionic substances.202 State the three categories of monatomic ions of the main-group elements.203 Write the electron configuration and Lewis symbol for a main-group ion.204 Note the polyatomic ions given earlier in Table 2.5.

205 Note the formation of 2+ and 3+ transition-metal ions.206 Write electron configurations of transition-metal ions.207 Define ionic radius.208 Define isoelectronic ions.209 Use periodic trends to obtain relative ionic radii.210 Describe the formation of a covalent bond between two atoms.211 Define Lewis electron-dot formula.212 Define bonding pair and lone (nonbonding) pair of electrons.213 Define coordinate covalent bond.214 State the octet rule.215 Define single bond, double bond, and triple bond.

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216 Define polar covalent bond.217 Define electronegativity.218 State the general periodic trends in the electronegativity.219 Use electronegativity to obtain relative bond polarity.220 Write Lewis formulas with single bonds only.221 Write Lewis formulas having multiple bonds.222 Write Lewis formulas for ionic species.223 Define delocalized bonding.224 Define resonance description.225 Write resonance formulas.226 Write Lewis formulas (exceptions to the octet rule).227 Note exceptions to the octet rule in Group IIA and Group IIIA elements.

228 Define formal charge.229 State the rules for obtaining formal charge.230 State two rules useful in writing Lewis formulas.231 Use formal charges to determine the best Lewis formula.232 Define bond length (bond distance).233 Define covalent radii.234 Define bond order.235 Explain how bond order and bond length are related.236 Define bond energy.237 Estimate H from bond energies.

Molecular Geometry and Chemical Bonding Theory

The Valence-Shell Electron-Pair Repulsion (VSEPR) Model238 Define molecular geometry.239 Define valence-shell electron-pair repulsion model.

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240

Note the difference between the arrangement of electron pairs about a central atom

and molecular geometry.241 Note the four steps in the prediction of geometry by the VSEPR model.242 Predict the molecular geometry (two, three, or four electron pairs).

243

Note that a lone pair tends to require more space than a corresponding bonding pair

and that a multiple bond requires more space than a single bond.244 Predict the molecular geometry (five or six electron pairs).245 Define dipole moment.246 Explain the relationship between dipole moment and molecular geometry.

247

Note that the polarity of a molecule can affect certain properties, such as a boiling

point.

Valence Bond Theory248 Define valence bond theory.

249State the two conditions needed for bond formation, according to valence bond theory.

250 Define hybrid orbitals.251 State the five steps in describing bonding, following the valence bond theory.252 Apply valence bond theory (two, three, or four electron pairs).

253 Apply valence bond theory (five or six electron pairs).254 Define (sigma ) bond.255 Define (pi ) bond.256 Apply valence bond theory (multiple bonding).

257

Explain geometric, or cistrans, isomers in terms of the p-bond description of a double

bond.258 Define molecular orbital theory.259 Define bonding orbitals and antibonding orbitals.260 Define bond order.

261

State the two factors that determine the strength of interaction between two atomic

orbitals.

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262 Describe the electron configurations of H2, He2, Li2, and Be2.

263 Define homonuclear diatomic molecules and heteronuclear diatomic molecules.264 Describe molecular orbital configurations (homonuclear diatomic molecules).265 Describe molecular orbital configurations (heteronuclear diatomic molecules).

266 Describe the delocalized bonding in molecules such as O3.

States of Matter; Liquids and Solids

267Compare a gas, a liquid, and a solid using a kineticmolecular theory description.

268 Define change of state (phase transition).269 Define melting, freezing, vaporization, sublimation, and condensation.270 Define vapor pressure.

271

Describe the process of reaching a dynamic equilibrium that involves the vaporization

of a liquid and condensation of its vapor.272 Define boiling point.273 Describe the process of boiling.274 Define freezing point and melting point.275 Define heat (enthalpy) of fusion and heat (enthalpy) of vaporization.276 Calculate the heat required for a phase change of a given mass of substance.

277Describe the general dependence of the vapor pressure (ln P) on the temperature (T).

278 Calculate the vapor pressure at a given temperature.279 Calculate the heat of vaporization from vapor pressure.280 Define phase diagram.

281Describe the melting-point curve and the vapor-pressure curves (for the liquid and thesolid) in a phase diagram.

282 Define triple point.283 Define critical temperature and critical pressure.

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284 Relate the conditions for the liquefaction of a gas to its critical temperature.285 Define intermolecular forces.286 Define dipoledipole force.287 Describe the alignment of polar molecules in a substance.288 Define London (dispersion) forces.289 Note that London forces tend to increase with molecular mass.290 Relate the properties of liquids to the intermolecular forces involved.291 Define hydrogen bonding.292 Identify the intermolecular forces in a substance.293 Determine relative vapor pressures on the basis of intermolecular attractions.294 Define molecular solid, metallic solid, ionic solid, and covalent network solid.295 Identify types of solids.296 Relate the melting point of a solid to its structure.297 Determine relative melting points based on types of solids.298 Relate the hardness and electrical conductivity of a solid to its structure.299 Define crystalline solid and amorphous solid.300 Define crystal lattice and unit cell of a crystal lattice.

301

Define simple cubic unit cell, body-centered cubic unit cell, and face-centered cubic

unit cell.302 Determine the number of atoms in a unit cell.303 Describe the two kinds of crystal defects.304 Define hexagonal close-packed structure and cubic close-packed structure.305 Define coordination number.

306

Note the common structures (face-centered cubic and body-centered cubic) of metallic

solids.307 Describe the three types of cubic structures of ionic solids.308 Describe the covalent network structure of diamond and graphite.309 Calculate atomic mass from unit-cell dimension and density.310 Calculate unit-cell dimension from unit-cell type and density.

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Solutions and Surface Chemistry311 Define solute and solvent.312 Define miscible fluid.313 Provide examples of gaseous solutions, liquid solutions, and solid solutions.

314

List the conditions that must be present to have a saturated solution, to have

an unsaturated solution, and to have asupersaturated solution.315 Describe the factors that make one substance soluble in another.316 Determine when a molecular solution will form when substances are mixed.317 Learn what conditions must be met in order to create an ionic solution.318 State the general trends of the solubility of gases and solids with temperature.319 Explain how the solubility of a gas changes with temperature.320 Apply Henrys law.

321 Define colligative property.322 Define molarity.323 Define mass percentage of solute.324 Calculate with mass percentage of solute.325 Define molality.326 Calculate the molality of solute.327 Define mole fraction.328 Calculate the mole fraction of components.329 Convert molality to mole fractions.330 Convert mole fractions to molality.331 Convert molality to molarity.332 Convert molarity to molality.333 Explain vapor-pressure lowering of a solvent.334 State Raoults law.335 Calculate vapor-pressure lowering.

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336 Describe an ideal solution.337 Define boiling-point elevation and freezing-point depression.338 Calculate boiling-point elevation and freezing-point depression.339 Calculate the molecular mass of a solute from molality.340 Calculate the molecular mass from freezing-point depression.341 Describe a system where osmosis will take place.342 Calculate osmotic pressure.343 Determine the colligative properties of ionic solutions.344 Define colloid.345 Explain the Tyndall effect.346 Give examples of hydrophilic colloids and hydrophobic colloids.347 Describe coagulation.348 Explain how micelles can form an association colloid.

Rates of Reaction349 Define reaction rate.350 Explain instantaneous rate and average rate of a reaction.351 Explain how the different ways of expressing reaction rates are related.352 Calculate average reaction rate.

353 Describe how reaction rates may be experimentally determined.354 Define and provide examples of a rate law , rate constant, and reaction order.355 Determine the order of reaction from the rate law.356 Determine the rate law from initial rates.

357Learn the integrated rate laws for first-order, second-order, and zero-order reactions.

358 Use an integrated rate law.359 Define half-life of a reaction.

360Learn the half-life equations for first-order, second-order, and zero-order reactions.

361 Relate the half-life of a reaction to the rate constant.

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362 Plot kinetic data to determine the order of a reaction.363 State the postulates ofcollision theory.

364 Explain activation energy (Ea ).

365

Describe how temperature, activation energy, and molecular orientation influence

reaction rates.366 State the transition-state theory.367 Define activated complex.

368

Describe and interpretpotential-energy curves for endothermic and exothermic

reactions.369 Use theArrhenius equation.370 Define elementary reaction, reaction mechanism, and reaction intermediate.371 Write the overall chemical equation from a mechanism.

372 Define molecularity.373 Give examples of unimolecular, bimolecular, and termolecular reactions.374 Determine the molecularity of an elementary reaction.375 Write the rate equation for an elementary reaction.376 Explain the rate-determining step of a mechanism.377 Determine the rate law from a mechanism with an initial slow step.378 Determine the rate law from a mechanism with an initial fast, equilibrium step.379 Describe how a catalyst influences the rate of a reaction.380 Indicate how a catalyst changes the potential-energy curve of a reaction.381 Define homogeneous catalysis and heterogeneous catalysis.

Chemical Equilibrium382

Define dynamic equilibrium and chemical equilibrium.383 Apply stoichiometry to an equilibrium mixture.384 Define equilibrium-constant expression and equilibrium constant.385 State the law of mass action.

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386 Write equilibrium-constant expressions.387 Describe the kinetics argument for the approach to chemical equilibrium.388 Obtain an equilibrium constant from reaction composition.

389 Describe the equilibrium constantKp ; indicate howKp andKc are related.

390

ObtainKc for a reaction that can be written as a sum of other reactions of

knownKc values.

391 Define homogeneous equilibrium and heterogeneous equilibrium.392 WriteKc for a reaction with pure solids or liquids.

393 Give a qualitative interpretation of the equilibrium constant based on its value.394 Define reaction quotient, Q.

395 Describe the direction of reaction after comparing Q withKc .

396 Use the reaction quotient.397 Obtain one equilibrium concentration given the others.398 Solve an equilibrium problem (involving a linear equation in x).399 Solve an equilibrium problem (involving a quadratic equation in x).400 State Le Chteliers principle.

401

State what happens to an equilibrium when a reactant or product is added or removed.

402 Apply Le Chteliers principle when a concentration is altered.403 Describe the effect of a pressure change on chemical equilibrium.404 Apply Le Chteliers principle when the pressure is altered.405 Describe the effect of a temperature change on chemical equilibrium.406 Apply Le Chteliers principle when the temperature is altered.407 Describe how the optimum conditions for a reaction are chosen.408 Define catalyst.409 Compare the effect of a catalyst on rate of reaction with its effect on equilibrium.410 Describe how a catalyst can affect the product formed.

Acids and Bases

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411 Define acid and base according to the Arrhenius concept.412 Define acid and base according to the BrnstedLowry concept.413 Define the term conjugate acidbase pair.414 Identify acid and base species.415 Define amphiprotic species.416 Define Lewis acid and Lewis base.417 Identify Lewis acid and Lewis base species.

418

Understand the relationship between the strength of an acid and that of its conjugate

base.419 Decide whether reactants or products are favored in an acidbase reaction.420 Note the two factors that determine relative acid strengths.421 Understand the periodic trends in the strengths of the binary acids HX.

422 Understand the rules for determining the relative strengths of oxoacids.423 Understand the relative acid strengths of a polyprotic acid and its anions.424 Define self-ionization (or autoionization).425 Define the ion-product constant for water.

426Calculate the concentrations of H3O

+and OH

-in solutions of a strong acid or base.

427 DefinepH.428 Calculate the pH from the hydronium-ion concentration.429 Calculate the hydronium-ion concentration from the pH.430 Describe the determination of pH by a pH meter and by acidbase indicators.

Acid-Base Equilibria

431Write the chemical equation for a weak acid undergoing acid ionization in aqueoussolution.

432 Define acid-ionization constant and degree of ionization.

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433 DetermineKa from the solution pH.

434

Calculate concentrations of species in a weak acid solution usingKa (approximation

method).

435State the assumption that allows for using approximations when solving problems.

436

Calculate concentrations of species in a weak acid solution usingKa (quadratic

formula).437 State the general trend in the ionization constants of a polyprotic acid.438 Calculate concentrations of species in a solution of a diprotic acid.

439

Write the chemical equation for a weak base undergoing ionization in aqueous

solution.440 Define base-ionization constant.

441 Calculate concentrations of species in a weak base solution usingKb .

442 Write the hydrolysis reaction of an ion to form an acidic solution.443 Write the hydrolysis reaction of an ion to form a basic solution.444 Predict whether a salt solution is acidic, basic, or neutral.

445 ObtainKa fromKb orKb fromKa .

446 Calculating concentrations of species in a salt solution.447 Explain the common-ion effect.448 Calculate the common-ion effect on acid ionization (effect of a strong acid).449 Calculate the common-ion effect on acid ionization (effect of a conjugate base).450 Define buffer and buffer capacity.451 Describe the pH change of a buffer solution with the addition of acid or base.452 Calculate the pH of a buffer from given volumes of solution.453 Calculate the pH of a buffer when a strong acid or a strong base is added.454 Define equivalence point.455 Describe the curve for the titration of a strong acid by a strong base.456 Calculate the pH of a solution of a strong acid and a strong base.

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457 Describe the curve for the titration of a weak acid by a strong base.

458

Calculate the pH at the equivalence point in the titration of a weak acid by a strong

base.459 Describe the curve for the titration of a weak base by a strong acid.

460

Calculate the pH of a solution at several points of a titration of weak base by a strong

acid.

Solubility and Complex-Ion Equilibria

461 Define the solubility product constant ,Ksp .

462 Write solubility product expressions.463 Define molar solubility.

464 CalculateKsp from the solubility (simple example).

465 CalculateKsp from the solubility (more complicated example).466 Calculate the solubility fromKsp .

467

Explain how the solubility of a salt is affected by another salt that has the same cation

or anion. (common ion )468 Calculate the solubility of a slightly soluble salt in a solution of a common ion.469 Define ion product.470 State the criterion for precipitation.471 Predict whether precipitation will occur, given ion concentrations.

472Predict whether precipitation will occur, given solution volumes and concentrations.

473 Definefractional precipitation.474

Explain how two ions can be separated using fractional precipitation.475 Explain the qualitative effect of pH on solubility of a slightly soluble salt.476 Determine the qualitative effect of pH on solubility.477 Explain the basis for the sulfide scheme to separate a mixture of metal ions.

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478 Define complex ion and ligand.

479

Defineformation constant or stability constant, Kf, and dissociation constant, Kd .

480 Calculate the concentration of a metal ion in equilibrium with a complex ion.481 Define amphoteric hydroxide.482 Predict whether a precipitate will form in the presence of the complex ion.

483Calculate the solubility of a slightly soluble ionic compound in a solution of thecomplex ion.

Energetics484 Define internal energy, state function, work, andfirst law of thermodynamics.

485

Explain why the work done by the system as a result of expansion or contraction

during a chemical reaction is -PV.486 Relate the change of internal energy, U, and heat of reaction, q .487 Define enthalpy, H.

488

Show how heat of reaction at constant pressure, qp , equals the change of enthalpy,

H.

489 Define spontaneous process.490 Define entropy.491 Relate entropy to disorder in a molecular system (energy dispersal).492 State the second law of thermodynamics in terms of system plus surroundings.493 State the second law of thermodynamics in terms of the system only.494 Calculate the entropy change for a phase transition.495 Describe how H - TS functions as a criterion of a spontaneous reaction.496 Define standard entropy (absolute entropy) .497 State the situations in which the entropy usually increases.498 Predict the sign of the entropy change of a reaction.

499

Express the standard change of entropy of a reaction in terms of standard entropies of

products and reactants.500

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501 Definefree energy, G.502 Define the standard free-energy change.503 Calculate G from H and S.504 Define the standard free energy of formation, DG .505 Calculate G from standard free energies of formation.506 State the rules for using G as a criterion for spontaneity.507 Interpret the sign of G .508 Relate the free-energy change to maximum useful work.509 Describe how the free energy changes during a chemical reaction.510 Define the thermodynamic equilibrium constant, K.511 Write the expression for a thermodynamic equilibrium constant.

512 Indicate how the free-energy change of a reaction and the reaction quotient arerelated.

513Relate the standard free-energy change to the thermodynamic equilibrium constant.

514 CalculateK from the standard free-energy change (molecular equation).515 CalculateK from the standard free-energy change (net ionic equation).

516

Describe how G at a given temperature ( G T) is approximately related to H and

S at that temperature.

517

Describe how the spontaneity or nonspontaneity of a reaction is related to each of the

four possible combinations of signs of H and S.518 Calculate G andK at various temperatures.

Thermochemistry519 State the law of conservation of energy.520 Define a thermodynamic system and its surroundings.521 Define heat and heat of reaction.

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522 Distinguish between an exothermic process and an endothermic process.523 Define enthalpy and enthalpy of reaction.524 Explain how the terms enthalpy of reaction and heat of reaction are related.525 Explain how enthalpy and internal energy are related.526 Define a thermochemical equation.527 Write a thermochemical equation given pertinent information.

528

Learn the two rules for manipulating (reversing and multiplying) thermochemical

equations.529 Manipulate a thermochemical equation using these rules.

530

Calculate the heat absorbed or evolved from a reaction given its enthalpy of reaction

and the mass of a reactant or product.531 Define heat capacity and specific heat.

532

Relate the heat absorbed or evolved to the specific heat, mass, and temperature

change.533 Calculate using this relation between heat and specific heat.534 Define calorimeter.

535

Calculate the enthalpy of reaction from calorimetric data (its temperature change and

heat capacity).

536 State Hesss law of heat summation.

537

Apply Hesss law to obtain the enthalpy change for one reaction from the enthalpy

changes of a number of other reactions.538 Define standard state and reference form.539 Define standard enthalpy of formation.

540

Calculate the heat of a phase transition using standard enthalpies of formation for the

different phases.

541

Calculate the heat (enthalpy) of reaction from the standard enthalpies of formation of

the substances in the reaction.

Electrochemistry

Learn the steps for balancing oxidationreduction reactions in acidic solution using the

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542 half-reaction method.543 Balance equations by the half-reaction method (acidic solution).

544

Learn the additional steps for balancing oxidationreduction reactions in basic

solution using the half-reaction method.545 Balancing equations by the half-reaction method (basic solution).546 Define electrochemical cell, voltaic (galvanic) cell, electrolytic cell, and half-cell.547 Describe the function of the salt bridge in a voltaic cell.

548

State the reactions that occurs at the anode and the cathode in an electrochemical

cell.549 Define cell reaction.550 Sketch and label a voltaic cell.551 Write the cell reaction from the cell notation.

552 Define cell potential and volt.553 Calculate the quantity of work from a given amount of cell reactant.554 Explain how the electrode potential of a cell is an intensive property.555 Define standard cell potential and standard electrode potential.556 Interpret the table of standard reduction potentials.557 Determine the relative strengths of oxidizing and reducing agents.558 Determine the direction of spontaneity from electrode potentials.559 Calculate cell potential from standard potentials.560 Calculate the free-energy change from electrode potentials.561 Calculate the cell potential from free-energy change.562 Calculate the equilibrium constant from cell potential.563 Calculate the cell potential for nonstandard conditions.564 Describe how pH can be determined using a glass electrode.

565

Describe the construction and reactions of a zinccarbon dry cell, a lithiumiodine

battery, a lead storage cell, and a nickel-cadmium cell.

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566 Explain the operation of a proton-exchange membranefuel cell.567 Explain the electrochemical process of the rusting of iron.568 Define cathodic protection.569 Define electrolysis.570 Learn the half-reactions for water undergoing oxidation and reduction.571 Predict the half-reactions in an aqueous electrolysis.572 Calculate the amount of charge from the amount of product in an electrolysis.573 Calculate the amount of product from the amount of charge in an electrolysis.

Nuclear Chemistry574 Define radioactive decay and nuclear bombardment reaction.

575 Learn the nuclear symbols forpositron, gamma photon, electron, neutron, proton.

576 Write a nuclear equation.577 Deduce a product or reactant in a nuclear equation.578 Describe the shell model of the nucleus.579 Explain the band of stability.580 Predict the relative stabilities of nuclides.581 List the six types of radioactive decay.582 Predict the type of radioactive decay.

583 Define radioactive decay series.584 Define transmutation.585 Use the notation for a bombardment reaction.586 Locate the transuranium elements on the periodic table.587 Determine the product nucleus in a nuclear bombardment reaction.588 Define radioactive decay constant.589 Calculate the decay constant from activity.590 Define half-life.591 Draw a typical half-life decay curve of a radioactive element.592 Calculate the half-life from the decay constant.593 Calculate the decay constant and activity from half-life.

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594

Determine the fraction of nuclei remaining after a specified time.595 Apply the carbon-14 dating method.596 State the ways in which radioactive isotopes are used for chemical analysis.597 Calculate the energy change for a nuclear reaction.598 Properties of alpha,beta and gamma rays599 Define nuclear binding energy and mass defect.600 Compare and contrast nuclear fission and nuclear fusion.

601

Explain how a controlled chain reaction is applied in a nuclear fission reactor using

a critical mass of fissionable material.602 Write the reaction of the nuclear fusion of deuterium and tritium.

Inorganic ChemistryChemistry of the Main-Group Elements

603 Note the low ionization energies and electronegativities of the metals.604 Give the principal oxidation states of the main-group elements.605 State the periodic trends in metallic characteristics.

Metals: Characteristics and Production606 Define metal, alloy, mineral, and ore.607 Define metallurgy.608 State the basic steps in the production of a metal.609 Define theBayer process .610

Describe the roasting of lead sulfide ore.611 Describe the electrolysis of molten lithium chloride.612 Define theDow process.613 Define the HallHroult process.

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614 Describe the chemical reduction of lead(II) oxide to lead metal.615 Give some methods for refining metals.

Bonding in Metals616 Describe the electron-sea model of metals.617 Describe the molecular orbital theory of sodium and magnesium metals.

Group IA: The Alkali Metals618 Note the reactivity of the alkali metals.619 Describe the metallurgy, reactions, and compounds of lithium.620 Describe the metallurgy, reactions, and compounds of sodium.621 Define the Solvay process.622 Describe some compounds of potassium.

Group IIA: The Alkaline Earth Metals623 Describe the metallurgy, reactions, and compounds of magnesium.624 Describe the metallurgy, reactions, and compounds of calcium.

Group IIIA and Group IVA Metals625 Describe the metallurgy, reactions, and compounds of aluminum.626 Define the Goldschmidt process.627 Describe the metallurgy, reactions, and compounds of tin and lead.

Hydrogen628 Describe some properties of hydrogen.629 Describe the commercial preparation of hydrogen.630 Define the steam-reforming process.631 Describe some reactions and compounds of hydrogen.632 Define a binary hydride.

Group IVA: The Carbon Family633 Define catenation.634 Describe some allotropes of carbon.635 Describe the chemical properties of the oxides of carbon.636 Describe the chemical properties of the carbonates.

14

637 Describe the preparation of extremely pure silicon.638 Define silica.639 Describe the uses of quartz.640 Define silicate, condensation reaction, and silicone.

Group VA: Nitrogen and the Phosphorus Family641 Describe the properties and uses of nitrogen.642 Describe some nitrogen compounds.643 Define the Ostwald process.644 Describe the allotropes of phosphorus.645 Describe the phosphorus oxides and the oxoacids of phosphorus.646 Definepolyphosphoric acids and metaphosphoric acids.

Group VIA: Oxygen and the Sulfur Family

647 Describe the properties and preparation of oxygen.648 Describe some reactions of oxygen.649 Define oxide, peroxide, and superoxide.650 Describe the allotropes of sulfur.651 Describe the production of sulfur.652 Define the Frasch process and the Claus process.653 Describe the sulfur oxides and oxoacids.654 Define the contact process.

Group VIIA: The Halogens655 Describe chlorine and its properties, preparation, and uses.656 Describe the preparation of hydrogen chloride and its uses.657 Describe the preparation and uses of the oxoacids of chlorine.

Group VIIIA: The Noble Gases658 Describe the discovery, preparation, and uses of the noble gases.659 Describe some compounds of the noble gases.

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The Transition Elements and Coordination Compounds

Periodic Trends in the Transition Elements660 Identify the transition elements on the periodic table.

661

State the three characteristics that set the transition elements apart from the main-

group elements.662 Write electron configurations of the transition elements.663 Describe trends in atomic radii of the transition elements.664 Learn the common oxidation states of the fourth-period transition elements.

The Chemistry of Two Transition Elements665 Learn some of the common chromium compounds and their chemistry.666 Learn some of the common copper compounds and their chemistry.

Formation and Structure of Complexes

667

Define complex ion, complex (coordination compound) ligand, and coordination

number.

668Give examples of a monodentate ligand, bidentate ligand, andpolydentate ligand.

Naming Coordination Compounds669 Learn the four rules for naming coordination compounds.

670Write the IUPAC name given the structural formula of a coordination compound.

680Write the structural formula given the IUPAC name of a coordination compound.

Structure and Isomerism in Coordination Compounds681 Define constitutional isomers, stereoisomers , andgeometric isomers.682 Decide whether geometric isomers are possible.683 Define enantiomers (optical isomers ).684 Explain how structures are used to determine if an isomer is chiral.685 Describe how enantiomers are optically active.686 Define dextrorotatory, levorotatory, and racemic mixture.

15

ec e w e er op ca somers are poss e.

Extractive Metallurgy688 Carbon Reduction Method689 Self Reduction Method690 Electrolytic reduction Method691 Cyanide Process

Principles of Qualitative Analysis692 Group I to V as mentioned in the syllabus693 Nitrates, Halides ( excluding florides ), Sulphates and Sulphide

Organic Chemistry

Fundamentals of Molecular Structure and Chemical Reactivity

694

Sketch the 1s, 2s and 2p atomic orbitals (with mathematical signs) and write the

electronic configuration for all elements in the first two rows of the periodic chart.

695

Show in a sketch how the sp3, sp2 and sp hybrid orbitals may be constructed from the

simple atomic orbitals.

696

Explain the bond angle for the hydrides of all the elements through F using both the

VSEPR and hybridization models.697 Deduce molecular formula from composition and molecular weight.698 Calculate the formal charge on an atom in a small molecule.

699

Predict the direction and relative magnitudes of the dipole moments of simple

molecules.

700

Sketch a reasonable set of molecular orbitals for any 2-carbon molecule, showing the

mathematical signs of the lobes and approximate relative energies.

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701

Describe the molecular events occurring during melting and boiling for ionic and

covalent compounds and molecular crystals like diamond.

702

Predict the relative solubilities, melting points, boiling points and relative acidities

and basicities of simple compounds and explain your choice with reference to

structure.

703Explain by words and equations the factors affecting the rate of a chemical reaction.

704 Identify the major functional groups and types of reactions.

705

Calculate the pH of a solution of a weak acid or base from the analytical concentration

and Ka.

706

Calculate the concentrations of components in a chemical equilibrium from the

equilibrium constant and analytical concentrations.

The Alkanes and Cycloalkanes: Nomenclature, Conformation and

Confi uration

707

Name by the IUPAC system any saturated hydrocarbon whose parent chain contains

10 or fewer carbon atoms and no more than two simple rings (or sketch the

hydrocarbon given its IUPAC name).

708

Sketch the conformations of ethane, propane, butane, cyclobutane, cyclopentane and

cyclohexane and simple substituted compounds derived from them.

709

Describe (graphically ) the relation between conformation and potential energy for

ethane, propane and butane and closely related compounds (Newman projections).

710

Describe (graphically) the relation between conformation and potential energy for

cyclohexane.

711

Calculate the relative energies of disubstituted (e.g. methyl) cyclohexanes, assuming

chair conformations and using the relative energies of monosubstituted cyclohexane or

butane.Define and recognize stereoisomer, enantiomer, diastereomer, conformation,

16

con iguration, meso, epimer, reso ution.

713

Given their structures, state whether 2 compounds are enantiomers or diastereomers

or some other kind of isomer.714 Predict the number of stereoisomers of a compound of known bonding.

715

Sketch a molecule with a chiral center so as to show unambiguously the configuration

using both Fisher projection and perspective drawing.

716

Predict from the structure whether a pair of stereoisomers can be interconverted by a

conformational change and thus might not be separable.717 Draw conclusions about the mechanism of a reaction from the stereochemistry.718 Given a proposed mechanism for a reaction, predict the stereochemistry.

719

Outline a synthesis (several steps) of a hydrocarbon using halogenation and metal

reductions.

720Outline syntheses of cyclopropane compounds using carbene-generating compounds.

The Alkenes, Alkadienes and Alkynes

ALKENES

721

Sketch the molecular orbitals (bonding and antibonding) for ethene and their relative

energies.

722

Name by the IUPAC system any alkene whose parent chain contains 10 or fewer

carbon atoms and sketch the alkene given its IUPAC name.

723

Define, recognize and name alkene diastereomers (cis/trans); predict the direction of

the difference in their physical properties and chemical stability.

724

Outline the synthesis of a given alkene from an alkyl (di)halide, alcohol, alkyne or

alkane (including stereochemistry).

725

Write chemical equations to describe the currently accepted mechanism(s) of

dehydrohalogenation of an alkyl halide (including stereochemistry). Explain how this

mechanism is deduced from the experimental data.

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726

Write chemical equations to describe the currently accepted mechanism(s) of

dehydration of an alcohol (including stereochemistry). Explain how this mechanism is

deduced from the ex erimental data.

727Describe the evidence for the existence of carbocations and their relative stabilities.

728 Predict and recognize simple carbocation rearrangements (H, CH3, C6H5).729 Predict the alkenes formed by elimination reactions of given starting materials.

730

Predict the products or use in a synthetic plan the following reactions of alkenes

(including stereochemistry): catalytic hydrogenation, addition of halogen and

hypohalite, addition of hydrogen halide, addition of water, oxymercuration, addition of

carbocations (polymerization and alkylation), hydroxylation, epoxidation, addition of

carbenes h droboration ozonol sis.

731

Use the molecular formula, and oxidation and reduction reactions to deduce structural

features of an alkene.

732

Write chemical equations to describe the currently accepted mechanism of addition of

halogens to alkenes (including stereochemistry). Explain how the mechanism is

deduced from the ex erimental data.

733

Write chemical equations to describe our current understanding of the mechanism of

addition of acids (HX, H3O+, H2SO4) to alkenes. Explain how the mechanism isdeduced from the ex erimental data.

734

Using a reasonable mechanism for the reaction, explain why the orientation of

addition of HBr is sometimes "anti-Markovnikov" and what experimental evidence

exists for the ex lanation.

735

Write the mechanism for the acid-catalyzed addition of an alkene to itself. Do the

same for free radical addition.736 Write the mechanism for the Wurtz reaction and decarboxylation reaction

CONJUGATED ALKENES -- DIENES

737

Use allylic halogen substitution as part of a synthetic outline, (distinguish conditions

yielding ionic addition and free-radical substitution).

17

738

Write contributors to the resonance hybrid for simple systems such as allyl radical

(cation), carbonate, nitro.

739

Sketch the pi molecular orbitals of butadiene and allyl and indicate their relative

energies in a sketch.

740

Predict the products, in order of relative amount, of the addition of halogen or acid to a

diene; give an explanation of the effect of temperature on the product distribution.

741

By considering the mechanism and the stabilities of intermediates, explain the

differences between the reactions of conjugated double bonds and isolated double

bonds.742 Outline the mechanism and stereochemistry of the Diels-Alder reaction

ALKYNES

742

Predict the products and use in a synthetic scheme the following reactions of alkynes:addition of hydrogen, halogen, hydrogen halides, water, boron hydrides, and salt

formation with ver stron base or reducin metals.

743

Outline a synthesis of an alkyne from an alkene, alkyl halide, dihalide or tetrahalide;

outline the synthesis of an internal alkyne from a terminal alkyne.744 Reactions of Alkenes and Alkynes with KMnO4 and ozone

745Preparation of Alkenes and Alkyne by elimination reaction , Electrophilic reaction

746 Preparation of Alkyne by addition reaction

747

Predict products and stereochemistry of a Diels-Alder reaction. Make a sketch of a

reasonable transition state for this reaction.

Alkyl Halides

748

Name any alkyl halide whose parent chain is 10 carbons or less by the IUPAC system

and sketch an alkyl halide given its IUPAC name or alkyl name.

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749

Write the mechanism for halogenation of methane. Describe the experiments from

which the mechanism was deduced and the reasoning which lead to the mechanism.

750

Calculate bond dissociation energies and heats of reaction given the energies for

various steps and draw mechanistic conclusions from this energy data (similarly heats

of activation .

751

Given energy data (or relative rate data) and other experimental information about a

reaction, sketch a graph of energy vs. reaction progress.

752

Predict the products (including order of abundance) of halogenation of an alkane and

explain your choice by reference to the mechanism.753 Explain the difference between a transition state and an intermediate.

754Explain the greater selectivity achieved in bromination compared to chlorination.

755

Use the existing experimental evidence to describe the basis of our current

understanding of the mechanisms of nucleophilic substitution at sp3 carbon. Write

chemical equations to outline the mechanism for a particular halide.

756

Use nucleophilic substitution in a synthetic plan of several steps, taking into

consideration elimination, rearrangement and stereochemistry. Note that some of

these reactions form carbon-carbon bonds.

757

Predict the products, including stereochemistry, of a nucleophilic substitution of an

alkyl halide.

758

Predict (and explain) the effect of alkyl, vinyl and aryl substituents on nucleophilic

substitution.

759

Given the identity of nucleophile, leaving group, substrate and solvent, predict

whether elimination or substitution will predominate for a particular alkyl halide

substrate.

760

Outline in chemical equations the mechanisms of elimination of alkyl halides. Describe

the experimental information collected about this reaction and how the mechanisms

are deduced from this information.

18

761 Define and use correctly the terms SN2, SN1, E2, E1.762 Outline syntheses using organomagnesium and organocopper compounds.763 Draw conclusions about the mechanism of a reaction from the stereochemistry.764 Given a proposed mechanism for a reaction, predict the stereochemistry.

765

Given the predominant diastereomer in a stereoselective or stereospecific reaction,

provide a mechanistic explanation for the preference.

766Describe the evidence for the existence of carbocations and their relative stabilities.

767 Predict and recognize simple carbocation rearrangements (H, CH3, C6H5).

Alcohols and Ethers

ALCOHOLS

768

Name any alcohol whose parent carbon chain consists of 10 or fewer atoms by the

IUPAC system and sketch the alcohol given its IUPAC name or carbinol name.

769

Predict the relative acidity of alcohols by referring to the stability of all species in the

equilibrium.

770

Using our current understanding of the mechanisms of the two addition reactions,

explain why simple acid- catalyzed addition of water can give a different product in

both stereochemistry and orientation from the hydroboration-oxidation. Note that the

oxymercuration (Hg(OAc)2) / reduction is more regioselective than simple acid-

catal zed addition of water.

771

Show how the mechanism of the hydroboration reaction is deduced from the

experimental data about the reaction. Write chemical equations to describe the

mechanism, showing transition states if necessary.

772

Write a reasonable mechanism for the Grignard and lithium aluminum hydride

synthesis of alcohols from carbonyl compounds.

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773

Outline a several-step synthesis involving preparation of an alcohol from an alkene

(two ways), a ketone or aldehyde, an alkyl halide, an ester, an epoxide or an ether.

774

Outline the currently accepted mechanisms of the substitution of an alcohol by halogen

using HX and describe the experimental evidence for the mechanism.

775

Use HX and thionyl chloride or the phosphorus halides for the conversion of an alcohol

to an alkyl halide in a synthetic plan (the differences may be important).

776

Use the oxidation reactions of alcohols to aldehydes, ketones and carboxylic acids in a

synthetic plan.

777

Given all the reagents and products in an alcohol oxidation by dichromate or

permanganate, determine the number of moles of each ingredient, i.e. balance the

equation. Outline the mechanism of the oxidation of an alcohol by chromate.

Aromatic Compounds

STRUCTURE and NOMENCLATURE

778

Explain the unusual stability of conjugated double bond systems by the valence bond

(resonance) and the molecular orbital (Huckel, aromaticity) methods; distinguish the

two a roaches.

779

Write contributor structures to the resonance hybrid for simple molecules (e.g. allylradical, butadiene, benzyl cation, vinyl ether, p-nitrophenol) and order the structures

in decreasin im ortance as contributors.

780

Explain the experimental basis for the concept of resonance or aromaticity, i.e. the

differences in properties between aromatic and similar non-aromatic compounds.

781

Sketch the molecular orbitals computed by the Huckel method for benzene, butadiene,

and allyl; assign relative energies.

782

Predict whether a molecule will be aromatic or antiaromatic (for single and condensed

rings, ions, and heterocycles). Prerequisite: determine if the concept of aromaticity is

a licable.

19

783

Use correctly the following terms: resonance, delocalized, resonance energy, hybrid,

orbital, bonding, antibonding, non-bonding, aromatic, antiaromatic.

784

Use the concept of resonance and/or aromaticity to account for polarity, basicity,

acidity, etc. of benzene derivatives such as phenol, aniline, nitrobenzene, compared to

non-con u ated analo s.

785

Name by the IUPAC system compounds with substituted benzene rings (e.g. p-

nitroaniline) and sketch substituted benzenes given their IUPAC names.

ELECTROPHILIC AROMATIC SUBSTITUTION

786

Write the mechanism of electrophilic substitution of benzene for nitration,

halogenation, alkylation, acylation, protonation, and sulfonation, including production

of the electrophile. Sketch contributors to the intermediate resonance-stabilized ion

and the electrophiles. Give experimental evidence for the mechanism.

787

Explain, by referring to the mechanism of the reaction, the effect of a previous

substituent on the reactivity and orientation of electrophilic aromatic substitution

consider resonance, inductive and steric effects .

788

Outline a several-step synthesis of a substituted benzene which requires careful choice

of order of substitution to put the substituents in the correct orientation. This

synthesis may involve, in addition to the reactions in 9, oxidation or reduction of a

substituent or use of a protecting group (e.g. acyl) and the choice of mild conditions for

substitution of aniline and henol.

789

Explain the ease with which substitution and elimination reactions occur at the carbon

to a benzene ring by application of the principles of resonance.

NUCLEOPHILIC AROMATIC SUBSTITUTION

790

Outline the mechanism of nucleophilic aromatic substitution and describe the

experimental evidence for our current understanding of the mechanism.

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791

Predict and explain the relative reactivity of substituted aryl halides toward

nucleophilic substitution by deduction from the mechanism of the reaction.792 Use nucleophilic aromatic substitution as a step in synthetic sequence.

793

From the experimental evidence, explain why nucleophilic aromatic substitutions in

the presence of very strong bases (like NH2-, C6H5-) proceed by elimination followed

by addition rather than through an anionic intermediate (benzyne).

MISCELLANEOUS

794

Outline a synthesis using the preparation of a benzenediazonium salt and its

substitution by halogen, hydrogen, cyanide, hydroxide with the correct reagents, and

the conversion of a diazonium salt into an azo d e. See Unit XI.795 Outline the synthesis of salicylic acid from phenol.796 Use the oxidation and reduction of aromatic rings in a synthesis.797 Identify likely cumulative toxins among aromatic compounds.

Carboxylic Acids and Their Derivatives

798

Name by the IUPAC system any carboxylic acid, ester, amide or anhydride with 10 or

fewer carbon atoms in the parent chain and sketch the above given their IUPAC

names and common names u to 4 carbons .

799

Analyze the causes of the relative acidities of carboxylic acids by considering the

inductive, resonance and steric effects on the neutral (conjugate acid) form and the

anionic (conjugate base) form; use a similar analysis to predict the acidities of others.

Similarly analyze phenols, alcohols and compare with carboxylic acids

800

Outline the synthesis of a given carboxylic acid from the appropriate alcohol, aldehyde,

methyl ketone, alkyl benzene, alkyl (aryl) halide, nitrile, amide, ester, anhydride, acyl

halide.

801

Outline the synthesis of an acyl halide, amide, substituted amide, ester (lactone) or

anhydride from a carboxylic acid directly or from acyl halide or anhydride or ester.

20

802

Outline the synthesis of compounds with the following functional groups from

carboxylic acids or their derivatives: alcohol (p, s, t), -haloacid, -aminoacid, ketone,

aldeh de.803 Describe and recognize lipids, phospholipids, soaps, nylon, proteins, polyesters.

804

Write the currently accepted mechanism for the acid-catalyzed hydrolysis of ester,

amide, anhydride or acyl halide to the corresponding carboxylic acid. Similarly base-

catalyzed hydrolysis. Explain the experimental basis for each mechanism.

805

Write the currently accepted mechanism for the acid-catalyzed preparation of an ester

from an acid and an alcohol and explain the experimental evidence from which it was

deduced.

806

Write the currently accepted mechanism for acid or base-catalyzed ester exchange

(transesterification) (exactly like hydrolysis and esterification).

807

Outline the mechanism and stereochemistry of the Diels-Alder reaction, e.g. for maleic

anhydride.

Aldehydes and Ketones as Electrophiles

808

Name any aldehyde or ketone which contains ten or fewer carbon atoms in its parent

chain by the IUPAC system.

809

Given alkanes, alkenes, alkyl halides, alcohols, ethers, carboxylic acids, ketones

(aldehydes) of similar molecular weight, order them in polarity, boiling point, and

solubility in water.

810

Outline a synthesis of an aldehyde or ketone from a given alcohol, carboxylic acid,

alkene, alkyne, or alkyl benzene (or a precursor of these).

811

Write the currently accepted mechanism of Friedel-Crafts acylation of aromatic

compounds and describe the experiments leading to this proposed mechanism.

812

Write the currently accepted mechanisms for the addition of hydride reagents,

Grignard reagents, (bisulfite) and cyanide ion to ketones and aldehydes.

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813

Write the currently accepted mechanisms for the addition of alcohols (and ammonia

and its derivatives) to ketones and aldehydes; describe the experimental basis for these

mechanisms, including the effect of pH. Show why some amines give imines and others

enamines.

814

Advanced topic: Write the mechanism of the Cannizzaro reaction and describe the

experimental basis for the mechanism.

815

Identify starting materials or products for the reactions of aldehydes and ketones withsilver ion (in ammonia), permanganate, dichromate, cyanide, (bisulfite), ammonia,

amines, hydrazine and its derivatives, alcohols, hydride reagents (at least two),

hydrogen, and Grignard and other organometallic reagents.

816

Use organometallic reagents in the synthesis of compounds with new carbon-carbon

bonds.

817

Use the reactions of aldehydes and ketones with oxidants, cyanide, ammonia and its

derivatives, alcohols, hydride and hydrogen in a short synthetic plan.

818

Give a brief summary of the mechanism of the Wittig reaction and use the reaction in

a synthetic plan. Recognize an ylide.

Carbonyl Compounds as Nucleophiles: Carbanions

819Write the currently accepted mechanisms for the acid-catalyzed and base-catalyzedinterconversion of keto and enol forms.

820

Write the mechanisms for the base-catalyzed and acid-catalyzed halogenation of

aldehydes and ketones and explain how the experimental evidence leads to these

mechanisms. Describe the mechanistic basis of the iodoform test.

821

Write the mechanism of the aldol condensation for any simple reactive aldehydes or

ketones. Describe the experimental evidence for this reaction mechanism.

822

Recognize aldol condensation products and use the crossed aldol condensation in a

practical sythesis.823 Write the currently accepted mechanism of the Claisen ester condensation.

21

824

Write the mechanism of formation of enamines and use them as an enol substitute in a

synthetic sequence forming new C-C bonds, esp. one in which an enolate reaction

mixture would be too basic.

825

Write the currently accepted mechanisms of the malonic and acetoacetic ester

syntheses. Use these reactions in a synthetic plan, including that of a barbiturate.

826

Write the mechanisms of the decarboxylation of -carbonyl acids and the base-

catalyzed reverse (Claisen) condensation of -dicarbonyl compounds.

827

Write the mechanism of and explain the reason for nucleophilic addition to the -

carbon of an , -unsaturated carbonyl compound, esp. by carbanions in the Michael

reaction.

828

Recognize products of a Michael reaction and use it in a simple synthetic scheme.

829

Use the above reactions and the Reformatsky (PBr3 + carboxylic acid) and Hell-

Vollhard- Zelinski reactions in a short synthetic sequence.

830

Recognize reactions similar to the Aldol and Claisen condensations with functional

groups similar electronically to carboxyls.

Amines and Amino Acids

831

Name any primary, secondary or tertiary aliphatic amine with 10 carbons or fewer in

the parent chain by the IUPAC system and sketch the amine given its IUPAC name.

Name aniline, pyrrole, pyridine and their derivatives.

832

Given a mixture of up to four organic compounds, outline their separation using a flow

chart, by acid-base and solubility properties and by chemical reactions from which they

can be recovered.

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833

Analyze the causes of the relative basicities of a series of amines by applying the

concepts of resonance, inductive and steric effects to explain the relative stabilities of

base and conjugate acid and predict the relative basicity of another amine. Repeat

using the acidities of the conjugate acids as your starting point (the way most chemists

do it .

834

Outline the synthesis of an amine using its preparation from a nitrile, nitro compound,

alkyl halide, amide or ketone. The synthetic route must be chosen to minimize

mixtures of primary, secondary and tertiary. Note that some synthetic methods change

the number of carbon atoms in the molecule.

835

Write the currently accepted mechanism for the preparation of amines from alkyl

halides. Explain why this technique is particularly useful for the preparation of -

aminoacids. Wh is the Gabriel s nthesis often referable?

836

Give several examples of biologically important amines and amides. Recognize indole,

quinoline, isoquinoline alkaloids and 2-arylethylamines.

837

Advanced topic: Write the mechanism of the Hofmann degradation of amides to amines

and comment on the experimental data leading to this complex mechanistic sequence.

838

Outline the steps in the (Hofmann) elimination of amines to form alkenes for

identification. Given the product alkene and other spectroscopic and chemicalinformation, deduce the structure of the ori inal amine.

839

Outline the currently accepted mechanism of the formation of N-substituted amides

from amines using experimental observations to support the mechanism.

840 Explain the high reactivity of aniline toward ring substitution.841 Explain the chemical basis and practical use of the Hinsburg test.

842

Propose a mechanism for the reductive amination of a ketone or aldehyde using what

you have already learned about reactions of carbonyl compounds and catalytic

reduction with h dro en.

Outline simple syntheses of amino acids using reactions learned for amines and acids.843

.

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Skills Iit Jee Chemistry