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HW: HW#1; TEXT BOOKS DUE by June 6 th Hand in any day. Do Now: Heading on all papers; Complete notes p. 1 based on your prior knowledge of Chemistry and the reading packet. Today: 1.Intro to Organic 2.Bonding of Carbon 3.Homologous series of Hydrocarbons 4.Chemical vs Structural vs condensed structural formulas 5.Naming and Drawing basic Carbon compounds 6.Practice U14D1: Carbon Chemistry

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Organic Chemistry: Last Unit! HW: Complete HW #1

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Organic Chemistry is the study of carbon and most carbon compounds. Elemental carbon is found in nature as a solid. However, this solid can make many different forms, such as diamond and graphite. Carbons properties make possible an incredible variety of compounds, many of which form the basis for life itself. In this unit you will be introduced to the wide variety of organic compounds and the types of reactions they undergo. We use the IUPAC (International Union of Pure & Applied Chemistry) system to name organic compounds.

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I.Bonding of Carbon Atoms A. Carbon has a unique ability to form many different compounds -This is based on the tendency of carbon atoms to _________ bond with other carbon atoms and form ___________________. - One carbon atom can form a maximum of _________ covalent bonds Covalently Long chains 4

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B. Properties of Carbon Bonds: Review 1. Covalently bonded to each other 5. _____________ to react 4. Most are ____________ and tend to dissolve in non-polar solvents 3. _________ conductors of heat and electricity 2. Generally have _________ melting points and ________ boiling points Low Poor Non-polar slow

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C. The Bonding Behavior of Carbon 1. Carbon atoms share electrons to form _________________ (a single line = pair of shared electrons (2 e- s) ) - Carbons share one pair of electrons = ____________ - Carbons share two pairs of electrons = ___________ - Carbons share three pairs of electrons = __________ Covalent Bonds Single Bond Double Bond Triple Bond

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D. Molecular Formula vs. Structural Formulas vs. Condensed Structural Formula 1. Molecular Formula shows the type and the # of atoms involved Examples: C 4 H 10 C 2 H 4 C 8 H 18

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2. Structural Formula shows the arrangement of atoms and bonds in a molecule

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3. Condensed Structural Formula shows the arrangement of atoms in a molecule, without including all the bonds between atoms Examples: CH 3 CH 2 CH=CHCH 3 CH 3 -(CH 2 ) 4 -CH 3

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II. HYDROCARBONS A. Definition: Organic compounds that contain only atoms of _______ and ________. B. Homologous series of compounds: each member differs from the previous member by an increment small group of atoms, _________ composed of one ____ and two ____.

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1.) Alkanes Single bonds only between carbon atoms Homologous series of ______________ hydrocarbon

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2.)Alkenes (-ene) -Chain of carbon atoms with one ____________ bond between C atoms -Homologous series of _____________ hydrocarbons -After 3 Cs must give # of C where the double bond is located, (lowest #)

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3.)Alkyne: (-yne) -Chain of carbon atoms with one _________ bond between C atoms -Homologous series of ______________ hydrocarbons -After 3 Cs must give # of C where the triple bond is located, (lowest #)

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C. Naming Simple Hydrocarbons Use Reference Table P & Q. 1. Determine the number of carbons in the chain 2. Choose the appropriate prefix from Table P 3. Determine the type of bonding found in the chain from Table Q (single, double or triple) 4. Choose the suffix ane, -ene or yne for single, double or triple bonding respectively

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Practice: Tell if the following are saturated or unsaturated hydrocarbons C 2 H 2 _______________d) C 6 H 10 _______________ C 5 H 12 _______________e) C 7 H 14 _______________ C 3 H 8 _______________f) C 7 H 16 _______________ Name the following (the location of the double or triple bond has been given if necessary!) a) C 2 H 2 ____________________ d) C 4 H 6 1- _____________________ b) C 5 H 12 ___________________ e) C 7 H 14 3-_____________________ c) C 3 H 6 ____________________ f) C 4 H 10 _______________________

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D. Drawing structural formulas when the Molecular Formula is given in Practice #2 above a)C 2 H 2 b) C 5 H 12 c) C 3 H 6 C.F. : ______________ _____________________ _________________ d) C 4 H 6 (1-)e) C 7 H 14 (3-) f) C 4 H 10 ___________________ _____________________ __ ________________

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May 30 U13D2:Isomers and branched chain hydrocarbons HW:Study, review; Orgo Chem Big Fat Fake test Do Now: 1.HW out for check 2.Alone: w/o notes: do WS you picked up 3. In pairs. Complete the two tables in the notes packet, One table per person.then check each others work. Today: 1.Review 2.Isomers and branched CDs

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B) Name the following compounds:

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ANSWER D and E in complete sentences. D) Explain in detail what each part of the name 3-heptene means. Hept = 7 carbons in the chain -ene = double bond 3- = double bond is between the 3 rd and 4 th carbons in from the end of the molecule. E) Why is it necessary for the names to be so specific when naming organic compounds ? F) Draw the structural formula for 2-pentene.

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G) Draw the dot diagram for a 2-pentene molecule.

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E. Drawing structural formulas when the Name of the Organic Compound is given 1. determine how many carbons are in the chain based on the prefix and Table 2. draw the carbon chain 2-pentene 3. look at the ending: ane, -ene or yne

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4 th insert the single bonds if there is a number in front of the name (ex. 2-butene) that number tells you where to place the double (-ene ending) or triple bond (-yne ending) 5 th add hydrogen atoms (carbon has 4 bonds)

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Your Turn: Complete the Example 2 b) 2-hexyne Structural Formula: Condensed Formula: c) nonane Structural Formula: Condensed Formula:

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F. ISOMERS I) Example: C 4 H 10 Butane: Example: C 5 H 12 Pentane

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Definition the structure must make a line (--), a T or t but not an L T and t structures branched hydrocarbons physical properties and the chemical properties will differs between isomers

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Structural isomers can also involve the position of a double or triple bond. 1 - pentyne vs. 2-pentyne ___________ ___________ Molecular Formula

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II) Naming Branched-Chain Hydrocarbons hydrocarbons chains which have smaller carbon chains branching off the main chain of carbon atoms

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Naming Branched Hydrocarbons: 1) When straight-chain hydrocarbons have attached groups these also must be named These groups are called ______________ groups. * The CH 3 - group off the main chain is called a methyl group. * The CH 3 -CH 2 group off the main chain is called an ethyl group. The CH 3 -CH 2 -CH 2 group off the main chain is called an propyl group *More than 1: then use the prefixes: di =2, tri = 3, tetra= 4

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2) We also need to show the location of the branch off the main chain so we give the ________________ of the carbon atom it falls on. Example 1: methylbutane -main chain of C = 4 carbons (but-) -on the 2 nd carbon is a CH 3 group = methyl- -no number is needed b/c the only be branched if on a the 2 nd C in either direction the name the branched group, then end with the main chain name

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Practice Drawing and Naming Branched Chain Hydrocarbons: STRUCTURAL FORMULANAME

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June 2, 2014 Text books on front desk please Today Why are there so many organic compounds? HW: #2 due next class Do Now: CRT open to table R; notes p. 11

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STRUCTURAL FORMULANAME 3-ethyl-3-methyl-hexane 2-methyl-3-ethyl heptane 2,3-diethylpentane

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III. FUNCTIONAL GROUPS many other compounds form when other atoms replace one or more hydrogen atoms in a hydrocarbon. These atoms or groups of atoms are called functional groups. Reference Table R: The Organic Rosetta Stone: How will it help you? The Rosetta Stone is therefore no longer unique, but it was the essential key to modern understanding ofAncient Egyptian literature and civilization. The term Rosetta Stone is now used in other contexts as the name for the essential clue to a new field of knowledge.Ancient Egyptian literaturecivilization

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Note if a number is needed in the naming, the example given shows at what number of carbons, you must start using a number. Examples: _____________________________________________ If there is no number in the example, a number is NEVER needed! Examples: _____________________________________________

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HALIDES _____________________________________________________ Compound is called a ______________________ Naming: ______________________________________ Examples of Halocarbons: Naming/Drawing a Halocarbon 1. 2.) 1,1-dichlorobutane It is a halocarbon, or an alkyl halide. names, number & position are considered last, Halogen atoms bonded to a hydrocarbon

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Addition and Substitution Reactions Hydrocarbons undergo two simple kinds of reactions, the products of which are called hydrocarbon derivatives, hydrocarbon substitution products, or substituted hydrocarbons. 1) Substitution Reactions

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The hydrogen replaced is almost always the ones that are on the end of the hydrocarbon molecule. The hydrogen get replaced ONE AT A TIME. The reactive halogen atoms substitute for hydrogen atoms, hence the name. C 3 H 8 + Cl 2 C 3 H 7 Cl + HCl One chlorine atom replaces a hydrogen atom. C 4 H 10 + HBr C 4 H 9 Br + H 2 the bromine atom replaces one hydrogen atom

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2) Addition Reactions If an unsaturated hydrocarbon (alkene or alkyne) is reacted with a halogen, the mechanism of the reaction is such that the multiple bond is broken, and the halogen adds on at the site of the newly available bonds.

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C 3 H 6 + Cl 2 C 3 H 6 Cl 2 the chlorine adds to the molecule. C 4 H 8 + HBr C 4 H 9 Br the bromine and hydrogen atoms add to the molecule. Addition reactions are used when you need to make a molecule where halogen atoms are on adjacent (next to each other) carbons. If you want to make 1,4 dichloro butane, use substitution. If you want to make 2,3 dichloro butane, then addition is the reaction for you

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2. ALCOHOLS -The OH groups is called the _________________ group in organic chemistry - it DOES NOT form an ion in water - Naming: Examples of Alcohols The suffix of the parent name is -ol, and the position of the -OH group on the chain is indicated by the lowest-numbered carbon Hydroxyl

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Classifications of Alcohols Classifications of Monohydroxy (1-OH group) Alcohols - Primary Alcohol (1 o ) - Secondary Alcohol (2 o ) - Tertiary Alcohol (3 o ) Dihydroxy Alcohols- Trihydroxy Alcohols IUPAC Name:___________________ IUPAC Name:________________ Common Name: __________________

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ALDEHYDES - the bond is called a __________________ group *this group is found on the END CARBON of a chain* Naming : Examples of Aldehydes

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7.)methanal8.) octanal KETONES: * Thebond is called a _______________________ group *this group is found on the INTERIOR CARBON of a chain, NEVER the end C Naming :

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Examples of Ketones : (RCOR)

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5. ETHERS * General formula is written _______________ to show the oxygen bridge between the two carbon chains, breaks the chain into 2 parts for naming! Naming: Examples of Ethers

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U14D4: Functional groups continued... Today: Text books on front desk please Drawing and naming Acids, esters, amines and amides HW: See Schedule Do Now: Check point: CRT out; Clear desk Agenda: 1.Check 2.HW#2 answers 3.Notes 4.Practice

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6. ORGANIC ACID -COOH group Naming: ____________________________________ Examples of Organic Acids

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7.) octanoic acid

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7. ESTERS *General formula is written ______________ to show the oxygen bridge between the two carbon chains, breaks the carbon chains, *Esters are commonly formed from a reaction between a organic acid and an alcohol CH 3 COOH + CH 3 OH CH 3 COOCH 3 + H 2 O *Naming: O-R comes from the alcohol & is named 1 st with yl ending, RCO comes from the organic acid is named 2 nd with oate ending (think of abc order: alcohol, organic acid)

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Examples of Esters (RCOOR)

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8. AMINES - __________________________________ A derivative of ammonia: Naming: ____________________________________________________ Examples of Amines

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3.) 2-propanamine 4.) 3-pentanamine 9. AMIDES - ______________________________________________________ *amines react with carboxylic acids to form amides *a polyamide, many amides, is a protein! Naming: __________________

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10. AMINO ACIDS _________________________________________________ *Contains two functional groups from Ref table R --the organic acid group AND amine group ****Be able to recognize it**** * The amine group () is attached to the carbon atom that is adjacent to the acid group NH2 Examples of Amino Acids GLYCINE

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IV. ISOMERS: What are they again??? Definition: _______________________________________________________ Example: C 4 H 10 Butane: Example: C 5 H 12 Pentane

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A.Position of a functional group: molecular formula = C 3 H 7 OH B. Position of a double bond: molecular formula = C 4 H 8

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C. Position of a triple bond: molecular formula = C 4 H 6 D. Same molecular formula but different functional group! C 2 H 6 O Dimethyl ether (B Pt -23.6 o C)ethanol (B Pt 79 o C)

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U14D5: Organic Reactions Test books on front desk please! HW: See Schedule Do Now: 1. Look over Electrochem test, 2. Nomenclature Check; CRT R open Today: 1.Check 2.Electrochem Review 3.Orgo Reactions 4.Practice!

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3) Of Functional Groups and Families Homework A) Complete the following table:

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B) Draw the structures of the following organic compounds.

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_B___C) Which of the following molecules is an isomer of propanol? a) propanoneb) methyl ethyl etherc) propanald) propanoic acid

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V. ORGANIC REACTIONS *generally occur more slowly than inorganic reactions *relatively strong existing bonds must break before making new bonds * Catalyst use is a common practice

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1.) Substitution Reaction *Replaces hydrogen (H) in the molecule with another element *alkyl group can also be substituted creating branched alkanes What to look for: Reactant one alkane Products TWO of them: 1. the substituted hydrocarbon 2. small molecule called a by-product.

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2.) Addition Reaction * Breaking or ADDING across the double or triple bond *Form saturated hydrocarbon (single bonds). What to look for: Reactant DOUBLE OR TRIPLE BOND (Alkene or alkyne) Product ONE: the substituted hydrocarbon. C 5 H 10 + F 2 C 5 H 10 F 2

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3.) Combustion Reaction burning What to look for: Reactants Hydrocarbon or alcohol and O 2 Products CO 2 and H 2 O

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4.) Fermentation Oldest known Organic Reaction to man!!! Makes buzz in booze What to look for: Reactants: Glucose (C 6 H 12 O 6 ), (catalyst zymase) Products: CO 2 + Ethanol (C 2 H 5 OH)

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5.) Esterification making fruity & minty compounds esters by dehydration synthesis What to look for: Reactants Organic Acid (R-COOH) & an Alcohol (R-OH) Products The ester link R-COO-R and H 2 O CH 3 COOH + CH 3 OH CH 3 COOCH 3 + H 2 O

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6.) Saponification: SOAP!!!! This is what is made!!! (Reaction is the opposite of esterification) What to look for: Reactants Fat (a glycerol ester) + Base ( NaOH or KOH) Products Glycerol and soap (salt of the Organic Acid) (C 17 H 35 COO) 3 C 3 H 5 + 3 NaOH 3 C 17 H 35 COONa + C 3 H 5 (OH) 3

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7.) Polymerization Addition & Condensation Polymer: many parts - extremely large molecules Man-made: Nylon, polyester, polyethylene, polystyrene Natural: Linen, silk, cotton, wool, cellulose (paper), protein, starches Monomer: one part small molecules used to make the polymer, they are the building blocks of the polymer

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A. Addition Polymerization: Monomers are connected by breaking one of a double or triple bond to hook together 18 A ------------------> A-A-A-A-A-A-A-A-A-A-A-A-A-A-A-A-A-A or 18 A -(-A-)- 18 Reactants double or triple bond: n C 2 H 4 (n is a VERY BIG whole number) Products -(alkane) n - What to look for

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Ex.

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B. Condensation Polymerization: monomers are connected by removing a water molecule (dehydration synthesis) What to look for: Reactants: Amino acids or dihydroxy alcohol & double Organic Acid Products: H 2 O & the Polymer Ex.:Nylon

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8) Rubber a) cis- Polyisoprene (tires), polybutadiene (tires), polychloropropene (Neoprene...wire covering, automotive drive belts, wetsuit material)), Nitrile (automotive hoses and gaskets) 1.Formed by addition polymerization 2. The resultant macromolecule is tacky and not very strong. It generally has a low melting point.

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3. Vulcanization a process whereby the polymer chains are cross-linked with sulfur. This toughens up the rubber. **discovered accidentally by Charles Goodyear in 1839

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U14D6: Orgo review HW: See Schedule Do Now: 1. CRT open to R 2. Desk cleared;Checkpoint#2 Today: 1. Checkpoint 2. HW answer 3. Orgo reaction Review 4. Functional group review 5. Any questions? / work individually on review due

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C) Name the reaction type and reactants needed to form the following organic compounds: 1) propyl butanoate Type of Reaction:_____esterification___________ Reactants Needed:__1-propanol and butanoic acid 2) methyl propyl ether Type of Reaction:_____etherification_________ Reactants Needed:____methanol and 1-propanol_ 3) polypropylene Type of Reaction:___polymerization____________ Reactants Needed propylene and catalyst_____

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D ) Write the dehydration synthesis between 1-propanol and butanoic acid by drawing the structural formulas of the reactants and products. Name the product formed by this reaction.

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_ A__ 1) The reaction that occurs when a hydrocarbon is heated in the presence of oxygen is called a)combustionb) fermentation c) saponificationd) vulcanization _ D ___ 2) The cross-linking of rubber molecules with sulfur to toughen it is called a)combustionb) fermentation c) saponificationd) vulcanization _C ___3 ) The reaction that is used to manufacture soap is called a) Combustion b) fermentation c) saponificationd) vulcanization _ B ___ 4) The reaction that produces ethanol by the digestion of sugars by yeast is called a) Combustion b) fermentation c) saponificationd) vulcanization

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_ A ___5) Which reaction can be used to make 2,3 dichloro pentane? a)additionb) substitution c) etherificationd) esterification _ D ___6) Which reaction can be used to make propyl ethanoate? a)additionb) substitution c) etherificationd) esterification _ D ___7) What is a by-product of saponification? a)ethanoic acidb) propanone c) ethylene glycold) glycerol