History of Organic Chemistry - MOLEBUS (ALLCHEM) · Web view-CH- b. -CH2--CH3- d. -CH2= Which of the following is a condensed structural diagram for propane? C3H8 CH3-CH2-CH3 d. C-C-C

Organic Chemistry Testbank 1

History of Organic Chemistry

The first organic chemical to be synthesized in a lab from inorganic chemicals wasa. ethanol c. methaneb. sugar d. urea

The first person to synthesis an organic chemical from inorganic chemicals wasa. August Kekulé c. Friedrich Wöhlerb. John Dalton d. Raymond LeMieux

The Avitalism@ theory in organic chemistry held thata. organic chemicals can only be obtained from living organismsb. organic chemicals can only be obtained from dead organismsc. organic chemicals can only be obtained from living or dead organismsd. organic chemicals can be obtained from any source of chemicals, organic or

inorganic.Long Answer:Explain why Wöhlers synthesis of urea by heating ammonium cyanate crystals was a landmark event in the study of organic compounds.

Definition of Organic ChemistryOrganic chemicals

a. are all the compounds of carbon including the ionic compoundsb. are all the molecular compounds of carbon except the oxidesc. are all the ionic compounds of carbon including the oxidesd. can only be made by living organisms

Throughout history there have been many definitions of organic chemistry. The modern definition of organic chemistry refers to the study of

a. ionic compounds of carbonb. molecular compounds of carbonc. non-living substances onlyd. substances derived from living things.

Which is an organic chemical?a. CaCO3 c. Cl2

b. CCl4 d. CO2

Which is NOT an organic chemical?a. CH3COOH c. C4H7Ob. CO2 d. CCl4

Which is NOT an organic chemical?c. CH3CHO c. C2H6Od. CBr4 d. CO

Which substance is organic?a. AgCl c. NH4CNb. AgOCN d. (NH2)2CO

Multitude of Organic ChemicalsWhich statement is true?


a. Carbon can bond in chains with branches, but cannot form ringsb. Carbon can form single bonds, but not double and triple bonds.c. Carbon can bond in chains with branches, in rings, and with single, double and

triple bondsd. Carbon cannot form rings with double bonds or branches on them

Which statement is true?a. Over 90% of all known compounds are organicb. Over 90% of all known compounds are inorganicc. There are about 2 times as many inorganic compounds as organic compoundsd. There are about 2 times as many organic compounds as organic compounds

There are thousands of times more organic than inorganic compounds. The enormous number of carbon compounds is believed to be due, in large part, to the

a. high bonding capacity of a carbon atom.b. ability of carbon atoms to form covalent bonds with hydrogen.c. high number of lone pairs of electrons of a carbon atom.d. large variety of chemical reactions of elemental carbon

Short Answer:List three factors that contribute to the tremendous diversity of carbon compounds relative to the number of inorganic compounds.

Give two (good) reasons why carbon has its own branch of chemistry.

Homologous SeriesEach member of the alkane series differs from the preceding member by one additional carbon atom and

a. 1 hydrogen atom c. 2 hydrogen atomsb. 3 hydrogen atoms d. 4 hydrogen atom

The alkane family is referred to as a homologous series because each member of the family a. becomes more soluble in water as they get larger b. can have more isomers as they get larger c. has a boiling point that increases as they get largerd. increases by A-CH2" as they get larger

Which of the following is part of a homologous series:a. CH4, C2H4, C4H8 b. CH4, C2H2, C3H6

c. C3H8, C3H6, C3H4 d. C2H4, C3H6, C4H8

Which term describes this group of compounds?chloromethane, chloroethane, 1-chloropropane, 1-chlorobutane

a. aldehydes c. functional isomersb. aromatics d. homologous series

Alkanes/Straight chain alkanesAlkanes are:

a. organic compounds containing one or more carbon-carbon double bondsb. special group of unsaturated cyclic hydrocarbons


c. organic compounds containing one or more carbon-carbon triple bondsd. hydrocarbons that contain only single covalent bonds

How many double covalent bonds are in an alkane?a. none c. oneb. two d. The number varies

How many carbons are in a molecule of hexane?a. 3 b. 4b. 5 d. 6

What is the name of the alkane having five carbons?a. hexane c. methaneb. octane d. pentane

What increment of change occurs between propane and butane in the alkane series?B

a. -CH- b. -CH2-b. -CH3- d. -CH2=

Which of the following is a condensed structural diagram for propane?

a. C3H8

b. CH3-CH2-CH3 d.c. C-C-C

What is the name of the molecule on the right? a. butane b. pentane c. propaned. tetrane

What is the name of the molecule on the right?a. butane b. pentane c. propaned. hexane

What is the IUPAC name of the compound on the right? a. butaneb. decanec. propaned. pentane

What is the name of the straight chain alkane with 7 carbons?a. pentane c. hexeneb. heptane d. octyne

Branched Alkanes - NomenclatureWhich condensed structural formula represents the alkyl group called ethyl?

a. CHCH c. CH2CH3

b. CH2CH2 d. CH3CH3

What is the name of an alkyl group that contains two carbon atoms?a. diphenyl c. dimethyl


b. ethyl d. propylWhat prefix is used to represent the substituent CH3-CH2-CH2-?

a. ethyl- c. methyl-b. propyl- d. pentyl

If a substituent appears four times in an organic compound, what prefix is used?a. di- c. mono-b. penta- d. tetra-

What is the name of the compound on the right?a. 2,4-diethyl-2-methylhexaneb. 3-ethyl-5,5-dimethylheptanec. 5-ethyl-3,3-dimethylheptane d. 3,5-diethyl-5-methylhexane

What is the IUPAC name of compound on the right?a. 2-ethyl-3-dimethylhexaneb. 2-ethyl-3,3-diemethylhexanec. 4,4,5-trimethylheptaned. 3,4,4-trimethylheptane

What is the IUPAC name of compound on the right?a. 2,3-dimethylpentaneb. 3,4-dimethylpentanec. 3,4,4 -trimethylbutaned. 2,3,4-trimethylbutane

What is the IUPAC name of compound on the right?

a. trimethylpentaneb. 2-methyl-3-methyl-4-methylpentanec. 2,2-dimethyl-3-methylpentaned. 2,3,4-trimethylpentane

What is the IUPAC name of compound on the right?a. 2-ethyl-2,4,5-trimethylpentaneb. 2-ethyl-2,4-dimethylhexanec. 3,5,5-trimethylheptaned. 3,3,5-trimethylheptane

What is the correct IUPAC name for the compound shown below? CH3.CH(CH2.CH3).CH(CH3)2


a. 2,3-dimethyl pentane c. 1,1,2-trimethyl butaneb. 2-ethyl-3-methyl butane d. 3,4-dimethyl pentane

Which is the condensed structural formula for 2,2,3-trimethylbutane?a. CH3CH2(CH3)CH(CH3)2 c. CH3C(CH3)2C(CH3)3

b. CH3C(CH3)2CH(CH3)2 d. CH3CH2CH(CH3)C(CH3)3

What is the IUPAC name for this compound? CH3CH(CH3)C(CH3)3.a. 2,2,3-trimethylbutane c. tetramethylpropaneb. 1,1,1,2-tetramethylpropane d. heptane

Alkenes - NomenclatureAlkenes are:

a. organic compounds containing one or more carbon-carbon double bondsb. special group of unsaturated cyclic hydrocarbonsc. organic compounds containing one or more carbon-carbon triple bondsd. hydrocarbons that contain only single covalent bonds

Which hydrocarbon contains a double carbon to carbon bond?a. 1-butene c. 2-methylbutaneb. 1-butyne d. cyclobutane

Which compound is an alkene?a. butyne c. pentaneb. nonene d. propanone

What is the name of the molecule on the right? a. 2-ethyl-3-propyl-1-pentene b. 2,3-diethyl-4-methyl-1-pentenec. 3-ethyl-2,4-dimethyl4-hexened. 3,4-diethyl-2-methyl-4-pentene

What is the name of the molecule on the right? a. 2,3-dimethyl-4-propyl-4-penteneb. 2,3-dipropyl-1-butene c. 3,4-dimethyl-2-propyl-1-pentened. 4,5,6-trimethyl-4-heptene

What is the IUPAC name of this compound? a. 1,1-dimethyl-2-buteneb. 2-methyl-3-pentenec. 4-methyl-2-pentened. methylhexane

According to the rules established by chemists, what is the IUPAC name of the compound on the right?

a. 1-methyl-1-penteneb. 5-methyl-4-pentenec. 2,3-hexene


d. 2-hexene. Determine the IUPAC name for the following molecule:

a. 2,5-dimethyl-2-hexeneb. 2,5-dimethyl-4-hexenec. 2,5-dimethyl-2-heptened. 2,5-dimethyl-4-heptene

What is the name for the following molecule? a. 2-ethyl-2-penteneb. 4-ethyl-3-pentenec. 3-methyl-3-hexened. 4-methyl-3-hexene

The correct name for the compound (CH3)2CH.CH(CH3).CH2.CH:CH2 is: a. 4,5,5-trimethyl-1-pentene b. 4,5-dimethyl-1-hexene c. 2,3-dimethyl-5-hexene d. 4-propyl-4-methyl-1-butene

Alkynes - NomenclatureAlkynes are:

a. organic compounds containing one or more carbon-carbon double bondsb. special group of unsaturated cyclic hydrocarbonsc. organic compounds containing one or more carbon-carbon triple bondsd. hydrocarbons that contain only single covalent bonds

What is the name of the smallest alkyne?a. butyne c. ethyneb. methyne d. propyne

What is the name of the molecule on the right?a. 4,4-diethyl-2-butyneb. 4-ethyl-2-hexynec. 3-ethyl-4-hexyned. 1,1-diethyl-2-butyne

What is the name of the molecule on the right?a. 1,6,6,6-tetramethyl-2-pentyne b. 2,2-dimethyl-4-heptynec. 2,2,6-trimethyl-4-hexyned. 6,6-dimethyl-3-heptyne

Which is the condensed structural diagram for 4-methyl-2-pentyne?

a. c.


b. d.

What is the name of the molecule ?a. acetylene c. propyneb. 1-butyne d. propene

Cycloalkanes, cylcoalkene - Nomenclature

What is the name of the molecule on the right? a. ethylbenzeneb. ethylcyclohexanec. phenylethaned. propylcyclohexane

What is the name of the molecule on the right?a. butylcyclohexaneb. phenylpropanec. propylbenzened. propylcyclohexane

What is the name of the molecule on the right?a. ethylcyclopentaneb. pentylcyclopropanec. propylcylclopentaned. propylcyclohexane

What is the name of the molecule on the right?a. 2-ethylcyclopenteneb. 3-ethylcyclopentenec. 2-ethyl-2-cyclopentened. 5-ethyl-2-cyclopentene

What is the name of the molecule on the right?a. 2-methylcyclohexeneb. 3-methylcyclohexenec. 4-methylcyclohexened. 5-methylcyclohexene

Select the proper order of stability from least to most stable for the following cycloalkenes:


a. A, B, C c. C, A, Bb. B, C, A d. C, B, A

Simple Aromatics - nomenclatureWhat is the name of the molecule on the right?

a. 2-butylbenzeneb. butylbenzenec. phenylbutane d. propylbenzene

What is the name of the molecule on the right?a. butylbenzene b. 2-pentylbenzenec. pentylbenzened. phenylpentane

What is the IUPAC name of the compound on the right?a. pentylcyclohexaneb. cyclopentylhexanec. pentylbenzened. hexylbenzene

What is the IUPAC name of the compound on the right?a. butylbenzeneb. phenylbutanec. propylbenzened. phenylpropane

Phenyl Branches - nomenclature

What is the IUPAC name of the molecule on the right?a. 1,1,4-trimethyl-4-phenylbutane b. 2,4-dimethyl-5-phenylpentanec. 2,4-dimethyl-2-pentylbenzened. 2,4-dimethyl-1-phenylpentane

What is the IUPAC name of the molecule on the right?a. 2-methyl-3-ethyl-1-phenylbutane b. 2,3-dimethyl-1-phenylpentane c. 2,3-dimethyl-1-pentylbenzened. 3,4-dimethyl-5-phenylpentane

What is the IUPAC name for the molecule on the right?


a. 2-pentylbenzeneb. 2-phenypentanec. 1 -methyl-1-phenylbutaned. pentylbenzene

How many phenyl groups does the following molecule have? a. 0c. 2b. 1d. 6

Disubstituted benzenesWhat is another acceptable name for 1,3-dimethylbenzene?

a. m-dimethylbenzene c. o-dimethylbenzeneb. n-dimethylbenzene d. p-dimethylbenzene

What is another acceptable name for 1,4-dimethylbenzene?a. m-dimethylbenzene c. o-dimethylbenzeneb. n-dimethylbenzene d. p-dimethylbenzene

What is another acceptable name for 1,2-dimethylbenzene?a. m-dimethylbenzene c. o-dimethylbenzeneb. n-dimethylbenzene d. p-dimethylbenzene

What is the name of the molecule on the right?a. ethylmethylbenzeneb. o-ethylmethylbenzenec. m-ethylmethylbenzened. p-ethylmethylbenzene

What is the name of the compound on the right?e. diethylbenzenef. m-diethylbenzeneg. o-diethylbenzeneh. p-diethylbenzene

What is the name of the molecule on the right?a. ethylpropylbenzeneb. o-ethylpropylbenzenec. m-ethylpropylbenzened. p-ethylpropylbenzene

What is the IUPAC name for the isomeric compound on the right?a. 1,2-dichlorobenzene b. 1,3-dichlorobenzenec. 2,2-dichlorobenzened. 2,6-dichlorobenzene

Which of the following molecules is p-ethylmethylbenzene?


a. b.

c. d.Units of Unsaturation/general formulasWhat type of hydrocarbon is the compound on the right? CH3-CH2-CH2-CH2-CH2-CH3

a. aliphatic c. cyclicb. aromatic d. unsaturated

Which hydrocarbon is saturated?a. C6H6 c. C6H12

b. C6H10 d. C6H14

Which is the formula of a saturated hydrocarbon?a. C2H2 c. C2H4 b. C5H8 d. C5H12

Which is the formula of a saturated hydrocarbon?a. CH2CH2 c. C6H6

b. CH3CHCH2 d. (CH3)3CHA saturated continuous-chain hydrocarbon with seven carbons is _____.

a. cycloheptene c. hepteneb. heptane d. heptyne

Which of the following compounds is an unsaturated hydrocarbon?a. methane c. nonaneb. propyne d. ethyl

How many units of unsaturation does the molecular formula C5H8 have?a. none c. twob. one d. three

How many units of unsaturation does the molecular formula C7H12 have?a. none c. twob. one d. three

Which could be a molecular formula for an organic chemical with one ring and one double bond?

a. C5H10 c. C5H8

b. C6H14 d. C6H12

Which could be a molecular formula for an organic chemical with one ring?a. C5H10 c. C5H8

b. C6H14 d. C6H10


Which could be a molecular formula for a non-cyclic hydrocarbon with two double bonds?a. C5H10 c. C5H8

b. C6H14 d. C6H12

What is the molecular formula for 3,3-diethyl-4-methyl-1-hexyne?a. C10H18 c. C11H22

b. C11H20 d. C12H22

Which formula represents a member of the alkene series?a. C3H6 c. C2H2

b. C2H6 d. C6H6

Which formula represents a member of the alkane family?a. C3H6 c. C2H2

b. C2H6 d. C6H6

What is the general formula for a continuous-chain alkane?a. CnHn c. CnH2n-2

b. CnHn+2 d. CnH2n+2

To which class of aliphatic hydrocarbons does C25H52 belong?a. alkanes c. alkynesb. alkenes d. aromatics

Which of the following molecules is a saturated hydrocarbon?

a. b.

c. d.

Isomers:Which molecule is NOT an isomer of C4H8?

a. c.

b. d.Which molecule is NOT an isomer of C5H12?


a. c.

b. d.

C8H16 could have isomers witha. one ring or one double bond c. one ring and one double bondb. one triple bond d two rings

Which structural formula represents an isomer of 2-pentyne?a. c.

b. d.Which compound is an isomer of methylpropane?

a. butane c. pentaneb. cyclopropane d. propane

Which of the following compounds is a structural isomer of butane?a. 2-methylbutane c. 2,2-dimethylbutaneb. 2-methylpropane d. 2,2-diethylpropane

Which pairs of molecules are structural isomers?a. cyclohexane and 2,2-dimethylbutaneb. cyclohexene and 3,3-dimethyl-1-butynec. methylcyclobutane and 2-pentyned. 2-methylpentyne and 2-methylpentene

A structural isomer of hexane is _____.a. benzene c. cyclohexaneb. 2,2-dimethylbutane d. 2-methylpentene

Which compound can have isomers?a. C2H4 c. C2H2 b. C2H6 d. C4H8

How many structural isomers exist for the alkene CH2Br2? a. 1 c. 3b. b. 2 d. 4

Which compound is an isomer of CH3.CH2.CH2.CH2.OH a. CH3CH2OCH3 c. CH3CH2CH2CH3

b. CH3CH2CH2OH d. CH3CH(OH)CH2CH3 Which of the following pairs of compounds are isomers?

a. diethyl ether and 1-butanol b. 2-pentanone and 2-pentanol


c. pentanal and methyl butanoate d. propanoic acid and propanalStructural isomers have _____.

a. the same molecular formulab. different physical and chemical propertiesc. the same elemental compositiond. all of the above

Which of the following pairs of compounds are isomers?a. propanal and 1-propanolb. propanoic acid and propyl propanoatec. propanone and propanald. propyl ether and 1-propanol

Isomer - Short Answer

1a) A student is told to draw the structural diagram of the compound with formula C4H10 . Confused, the student tells the naive chemistry-challenged person that the task is impossible.a) Why can=t the student show the structure of C4H10? (2)b) Rephrase the question by changing one word so that the question can be answered, and then answer it. (Keep the flavor of the question - don't change it completely!) (4)1a) Give a brief explanation, using two examples, as to why the numbers are necessary for identifying an organic compound sometimes, but not other times. (4)b) Identify which of the following names need numbers in front to identify them completely: butanol, propanal, pentanone, hexene, butanoic acid, methylpentane.(3)

How many different answers should you get to the question, "What is the boiling point of C3H8O?" Explain with the use of structural diagrams, names and a brief discussion of intermolecular attractions.

Draw structural formulas for and name four isomers of C4H7Cl.

HalocarbonsWhich substituent would allow a compound to be classified as an alkyl halide?

a. fluorine c. oxygenb. nitrogen d. sulfur

The IUPAC name for the compound (CH3)2C(CH2.CH3).CH2.CHCl.CH3 is: a. 5-chloro-3,3-dimethylhexane c. 2-chloro-4-methyl-4-ethylpentaneb. 4-chloro-2-ethyl-2-methylpentane d. 1-chloro-1,3,3,3-trimethylpentane

What is the name of the molecule on the right?a. 2-dichloro-3-methylpentaneb. 2,2-dichloro-3-methylpentanec. 4,4-dichloro-3-methylpentaned. 4,4-dichloro-3,5-dimethylbutane

What is the name of the molecule on the right?a. 2,3-dichloro-2-methylpentaneb. 1,2-dichloro-1,1-dimethylbutane


c. 2,3-chloro-2-methylpentaned. 3,4-dichloro-4-methylpentane

The correct name for the molecule on the right is: a. 1,4,4-trifluoro-2-bromopentaneb. 2-bromo-1,4,4-trifluoropentanec. 2,2,5-trifluoro-4-bromopentaned. 4-bromo-2,2,5-trifluoropentane

AlcoholsWhat is the name of the molecule on the right?

a. butanoneb. 2-butanolc. 2-butanald. butyl ether

What is the name of the molecule on the right?a. 3-pentanoneb. 3-pentanal c. 3-pentanold. pentanoic acid

What is the correct IUPAC name for the compound shown below? CH3.CH2.CH(CH2.CH3).CH(OH).CH3

a. 3-ethyl-4-pentanol b. 2-methyl-5-hexanol c. 3-ethyl-2-pentanol d. 3-ethyl-2-heptanol

The correct IUPAC name for the compound CH3.CH2.CH2.C(CH3)2.OH is a. 1-hexanol c. 1- dimethylbutanolb. 1,1-dimethyl-1-butanol d. 2-methyl-2-pentanol

EthersWhich molecule is an ether?

a. c.

b. d.

Which of the following is an ether?


a. c.

b. d.What is the name of the molecule on the right?

a. butanalb. methylpropyl etherc. butanoned. methyl propanoate

What is the name of the molecule on the right?a. pentanalb. ethylpropyl etherc. pentanoned. ethyl propanoate

AldehydesWhich molecule is an aldehyde?

a. c.

b. d.

Which of the following is an aldehyde?

a. c.

b. d.


What is the IUPAC name of the molecule on the right?a. butanalb. 1-butanonec. butanoic acidd. propanal

What is the IUPAC name of the molecule on the right?a. butanalb. 1-butanonec. butanoic acidd. propanal

Which of the following is an aldehyde?a. butanone c. ethane b. ethanol d. pentanal

Which of the following is an aldehyde?a. butanal b. ethanonec. ethanol d. pentanoic acid

Ketones

What is the IUPAC name of the molecule on the right?a. ethylpropyl etherb. 3-hexanalc. 3-hexanoned. methyl butanoate

What is the IUPAC name of the molecule on the right?a. diethyl etherb. 2-pentanonec. 3-pentanoned. 3-pentanal

Which of the following is a ketone?

a. c.

b. d.

Which condensed structural formula represents a ketone?a. CH3CH2CH2OH c. CH3COCH3

b. CH3CH2CHO d. CH3CH2COOH

Carboxylic Acids


What is the IUPAC name of the molecule on the right?a. butanone b. ethanoic acidc. methy propanoate d. propanoic acid

What is the IUPAC name of the molecule on the right?a. butanal b. butanoic acidc. methy propanoate d. propanoic acid

What is the IUPAC name of the molecule on the right?a. pentanal b. pentanoic acidc. methy butanoate d. pentanone

EstersWhat is the IUPAC name of the molecule on the right?

a. butyl ethanoate b. ethyl propanoatec. ethyl butanoated. propyl ethanoate

What is the IUPAC name of the molecule on the right?a. ethyl methanoateb. methyl ethanoatec. ethanoic acidd. propanoic acid

What is the IUPAC name of the molecule on the right?a. ethyl propanoate b. methyl butanoate c. butyl methanoate d. methyl propanoate

Trivial Names

What is the IUPAC name of the molecule on the right?a. acetyleneb. formaldehydec. phenold. toluene

What is the IUPAC name of the molecule on the right?a. acetylene


b. formaldehydec. phenold. toluene

Fractional Distillation/Sources of hydrocarbons

Which molecule would condense closer to the top of a fractional distillation tower?a. C5H12 c. C14H30

b. C10H22 d. C20H42

Which molecule would condense closer to the bottom of a fractional distillation tower?a. C5H12 c. C14H30

b. C10H22 d. C20H42

Which is the correct statement regarding fractional distillation?a. The mixture of hydrocarbons in crude oil are converted into the various fractions

(gasoline, furnace oil, etc.) by chemical reactionsb. Substances with high boiling points will condense lower in the fractional

distillation tower.c. Fractions with very low boiling points will condense before the fractions with

high boiling pointsd. Crude oil from different sources, when distilled in a fractionating tower, will

yield the same percent of gasolineWhich compound in crude oil will be the first to evaporate relative to the other hydrocarbons listed?

a. decane c. heptaneb. nonane d. octane

What is not a source of raw materials for petrochemical industries?a. coal deposits c. crude oilb. mineral deposits d. natural gas

What is the main hydrocarbon component of natural gas?a. benzene c. ethane b. methane d. propane

Which type of coal has the highest carbon content?a. anthracite c. ligniteb. bituminous d. peat

Which process involves the conversion of once living organic matter to fossil fuels?a. carbonization c. combustionb. nuclear fusion d.. photosynthesis

Shapes of molecules

The bonding shape around every carbon in propane isa. bent c. tetrahedralb. linear d. trigonal planar


What is the shape of a methane molecule?a. bent c. pyramidalb. linear d. tetrahedral

The bonding shape around both carbons in ethyne isa. bent linear tetrahedral trigonal planar

Which of the following molecules is completely flat or planar?a. a. ethene b. ethane c. propene d. cyclohexane

Which description best describes the boding shape around the carbons in the molecule on the right?

a. trigonal planarb. linearc. tetrahedrald. cyclic

Short Answer:1. (a) Draw Lewis diagrams for ethane and ethyne.(b) Describe the shape around the carbon atoms in ethane versus ethyne.(c) How does the shape and arrangement of bonding electrons influence the reactivity of ethane versus ethyne?

Solubility

Which substance would be most soluble in water?a. propanoic acid c. propanalb. propanone d. propane

Which substance would be least soluble in water? a. propanoic acid c. propanalb. propanone d. propane

Which substance is immiscible with water?a. 2-butanol c. ethanalb. 2-methyl-3-heptene d. methanoic acid

In which of the following solvents would candle wax, C25H52, dissolve in the best?a. H2O c. C9H18

b. CH3OH d. C3H7OHIn which of the following compounds is hexane most likely to dissolve?

a. acetic acid c. ethyl alcoholb. decane d. water

nonane

Boiling Points

Which substance would have the highest boiling point?a. C7H12 c. C14H28

b. C9H16 d. C22H40


Which of the following compounds has the lowest boiling point?a. heptane c. 2,3-dimethylpentaneb. 2-methylhexane d. 2,2,3-trimethylbutane

Which substance would have the lowest boiling point?a. C7H12 c. C14H28

b. C9H16 d. C22H40

Which alkene has the highest boiling point at atmospheric pressure?a. C2H4 c. C4H8

b. C3H6 d. C5H10

What is the main force that influences boiling points in pure hydrocarbons?a. covalent bonding c. hydrogen bondingb. dipole-dipole attractions d. London Dispersion Forces

Which property is generally accepted as an indicator of the strength of intermolecular forces within a substance?

a. boiling point c. isomerismb. London dispersion force d. solubility

Alkanes, alkenes, and alkynes with the same number of carbons have: a. similar boiling and melting points primarily because they have nearly the same

molecular weightb. similar boiling and melting points primarily because they have similar polaritiesc. similar boiling and melting points primarily because they are nearly equal in

stabilityd. vastly different boiling and melting points

If alkenes of four carbons or less exist as gases at room temperature, how many alkenes exist as gases under these conditions?

a. 2 c. 4b. 3 d. 5

What is the physical state of the smallest alkanes (C1-C4) at room temperature?a. gas c. solidb. liquid d. gas or liquid

Intermolecular ForcesIn which substance would London dispersion forces be the only intermolecular force of attraction?

a. 1-pentanol c. pentanalb. pentanoic acid d. pentyne

Which substance would be able to form hydrogen bonds to water but would not have any hydrogen bonding between their own molecules?

a. ethanol c. propanalb. propanoic acid d. propanol

Hydrogen bonding is most noticeable ina. alkanes c. estersb. alkynes d. organic acids

Why is a carbon-hydrogen bond essentially nonpolar?


a. Neither atom is ionic.b. Free electrons cancel any polarity.c. The electron pair is shared almost equally.d. Van der Waals forces overcome polarity.

Lewis Dot Diagrams/Carbon BondingHow many valence electrons surround a carbon atom?

a. 1 c. 3b. 2 d. 4

How many covalent bonds does each carbon atom participate in an organic compound?a. 1 c. 3b. 2 d. 4

Which is the correct Lewis Dot diagram for acetylene, C2H2?

a. c.

c. d.

Benzene BondingWhat compound is the simplest of the arenes?

a. benzene c. ethyneb. ethene d. methane

Which of the following molecules does NOT have delocalized electrons?a. benzene c. cyclohexaneb. 2-phenylpentane d. toluene

The compound benzene puzzled chemists for many years. Empirical research indicates that carbon-carbon bonds in benzene are

a. all carbon-carbon single bondsb. all carbon-carbon double bondsc. neither double nor single bondsd. easily broken in chemical reactions.

Which chemical has delocalized electrons?

a. b.


c. d.What distinguishes benzene and benzene compounds from other organic compounds?

a. benzene and benzene compounds are planar moleculesb. carbon atoms in benzene have 120 bond anglesc. carbon atoms in the benzene ring have just three bonding electronsd. carbon-carbon bonds in benzene involve delocalized bonding electrons

Functional Groups/hydrocarbon derivatives

Which of the following is a hydrocarbon derivative?a. C3H8 c. C9H18

b. CH4 d. C3H70HAn arrangement of several atoms which gives characteristic properties to an organic molecule is known as a(an)

a. carboxyl group c. groupb. functional group d. alkyl group

What is primarily responsible for the chemical properties of a hydrocarbon derivative like ethanol?

a. its delocalized electrons c. its functional groupb. its level of saturation d. its solubility in water

In the general formula for alcohols, R-OH, the "R' representsa. radon c. the functional groupb. CH3 only d. an alkyl group

The functional group for aldehydes is:a. hydroxyl c. carboxylb. carbonyl d. ester

The functional group for ketones is:c. hydroxyl c. carboxyld. carbonyl d. ester

The functional group for alcohols is:e. hydroxyl c. carboxylf. carbonyl d. ester

The functional group for carboxylic acids is:g. hydroxyl c. carboxylh. carbonyl d. ester

Which compound contains the functional group called hydroxyl?a. CH3OH c. HCOOHb. H2CO d. NH4CH3COO

The functional group for alcohols is


a. hydroxyl c. carboxylb. carbonyl d. ester

Organic Reactions

Complete the following reactions by identifying reaction type, predicting products where necessary, drawing structures for ALL organic reactants and products and naming ALL products. Indicate if more than two products are possible.

Respiration/Photosynthesis:Which biological process produces glucose from carbon dioxide and water?

a. carbonization c. fusionb. photosynthesis d. respiration

Cracking/ReformingWhich reaction type uses ethene and low molecular weight hydrocarbons and converts them into gasoline grade hydrocarbons?

a. cracking c. esterificationb. elimination d. reforming

What is the name of the process in which large molecules are broken down into smaller molecules in order to increase the yield of gasoline from petroleum?

a. polymerization c. esterificationb. hydrogenation d. cracking

Which chemical reaction may be used to convert straight-chain aliphatic hydrocarbons to alkylated or branched hydrocarbons?

a. elimination c. esterificationb. reforming d. substitution

n-decane + H2 butane + _______

SubstitutionWhich is NOT a possible product in the reaction between benzene and 2 mol of bromine?

a. 1,3-dibromobenzene c. 1,2,3,4-tetrabromobenzeneb. o-dibromobenzene d. hydrogen bromide

Which is NOT a possible product in the reaction between benzene and 2 mol of chlorine?a. 1,2-dichlorobenzene c. 1,2,4,5-tetrachlorobenzeneb. p-dichlorobenzene d. hydrogen chloride

Which pairs of reactants are most likely to react by a substitution reaction?I. H2 II. Cl2 III.


C2H4 IV. C2H6

a. I and III

c.I and

IVb. II and III

d.II and

IVWhich pairs of reactants are most likely to react by a substitution reaction?

I. Br2 II. HBrIII. C2H6 IV. C2H4

a. I and III

c.I and

IVb. II and III

d.II and

IVWhich type of compound will undergo a substitution reaction with a halogen?

a. an alkane c. an alkyneb. an alkene d. a ketone

Based on the generalizations for reaction types, butane and fluorine gases react bya. addition c. combustionb. esterification d. substitution

Short answer: propane + 1 mol chlorinepentane + 1 mol bromine


benzene + 2 mol brominem-dimethylbenzene + chlorine butane + 2 mol brominepentane + Br2

hexane + chlorine

Addition

Which IS a product of the reaction between 2-butene and 1 mol of chlorine?a. 1,2-dichlorobutane c. 1,3-dichlorobutaneb. 2,3-dichlorobutane d. 1-4-dichlorobutane

Which IS a product of the reaction between propene and 1 mol of chlorine?a. 1,2-dichloropropane c. hydrogenb. 1,3-dichloropropane d. 1-chloropropane

Which is NOT a product of the reaction between 1-pentyne and 2 mol of hydrogen bromide?a. 1,1-dichloropentane c. 1,3-dichloropentaneb. 1,2-dichloropentane d. 2,2-dichloropentane

What type of reaction is C2H4+ H2 C2H6 ?a. addition c. condensationb. substitution d. esterification

Which equation represents an addition reaction?a. CH3CH3 + Cl2 CH3CH2Cl + HClb. CH2CH2 + Cl2 CH2ClCH2Cl c. CH3CH2Cl + OHB CH2CH2 + H2O + ClBd. CH2CH2 + CH3CH3 (CH3)2CHCH3

How many products will result when 1-butene reacts with water?a. 1 c. 3b. 2 d. 4

How many products will result when 2-butene reacts with water?a. 1 c. 3b. 2 d. 4

Which organic reactant will produce 3-chloropentane when reacted with hydrogen chloride?a. pentane c. 2-penteneb. 1-pentene d. 2-pentyne

Short answer2-pentyne + excess HCl 2-pentyne + 2 mol HCl2-butyne + 2 mol HBr1-butyne + 2 mol HCl 3-octene + hydrogen iodide


1-pentene + water1-butene + water3-heptene + water 4-methyl-1-butyne + 1 mol hydrogen

EsterficationWhich of the following pairs of compounds could be combined to synthesize the compound responsible for the odor of pears, pentyl ethanoate?

a. 1-pentanol and ethanol c. 1-pentanol and ethanoic acidb. ethanal and pentanoic acid d. ethanol and 1-pentene

Which substance would be the best choice as a catalyst for a reaction between octanoic acid and ethanol?

a. acetic acid c. methanolb. sodium hydroxide d. sulfuric acid

What is the organic product of the reaction of methanol and ethanoic acid?a. propanone c. ethyl methanoateb. propanal d. methyl ethanoate

Short answerethanoic acid + 1-pentanolpropanol + butanoic acidmethanoic acid + 1-pentanol 1-butanol + _________________ butyl propanoate

Hydrocarbon CombustionWhen hydrocarbons are burned completely, which product is always formed?

a. amorphous graphite c. limewaterb. carbon dioxide d. methane

Short answer2-methyl-1-butene + oxygen (Balance this reaction)2-methyl-1-hexene + oxygen (Balance this reaction)3-methyl-1-pentyne + oxygen 3,4-diethyl-2-pentene + oxygen

EliminationWhich substance will undergo an elimination reaction when reacting with hydroxide ions?

a. 2-fluoropropane c. ethanoic acidb. methyl methanoate d. propanal

Which compound, when heated in the presence of a strong acid, will produce a second compound that will react quickly with bromine, even in the dark?

a. acetylene c. 1-hexanol


b. 2-butene d. pentaneWhich reaction will not produce an alkene?

a. 2-chlorohexane is heated with sodium hydroxideb. 2-pentyne and hydrogen are mixed in the presence of a platinum catalystc. 1-propanol is warmed with butanoic acid in the presence of a strong acidd. 3-propanol is warmed in the presence of a strong acid

Short answer2-chlorobutane + hydroxide ions2-chlorobutane + sodium hydroxide 2-pentanol is warmed in the presence of a strong acid

ethanol

3-heptanol

Reaction type: _______________________

Identifying Polymerization

Identify the reaction type:

a. addition polymerization c. condesation polymerizationb. esterification d. hydrocarbon combustion

Identify the reaction type:

a. addition polymerization c. condesation polymerizationb. esterification d. hydrocarbon combustion


What monomer was used to produce the polymer:

a. b.

c. d.

Condensation Polymerization

Which polymer was produced by condensation polymerization?

a.


b.

c. d.

Long answer:Proteins are the building blocks of the human body. They are composed of chains of amino acids, and make up our skin, nails, hair and connective tissue. The type of protein formed depends upon the sequence of the amino acids in the chain.

Some amino acids are given below.

alanine glycine

cysteine Threonine

a. What type of reaction will link these amino acids into a long chained protein?b. What are the chemical characteristics of these molecules that allow them to form

long chains? Pick one of the amino acids to illustrate your answer.c. The protein in hair will curl around in a helix shape, held together by hydrogen

bonds. Draw a dotted line to show where hydrogen bonding could occur if cysteine and threonine were close together on two different protein chains. (2)

Addition PolymerizationWhich substance will undergo addition polymerization?a. 1-propanol c. propanalb. propanone d. propeneWhich monomer will produce the polymer on the right?a. 1-penteneb. 2-pentenec. ethylmethylethaned. pentane

Which synthetic polymer is the product of addition polymerization?a. cellulose c. ribonucleic acid (RNA)b. protein d. teflon

Short answeraddition polymerization reaction with 1-penteneaddition polymerization reaction with 1-butenen 2-pentyne

Long Answer Questions:

When ethene reacts with chlorine in the absence of light, only one product forms. However, if ethene reacts with chlorine in the presence of light, over a long period of time, many products are formed.

a. Identify the reaction type when ethene reacts in the absence of light, and write equation to show the product formed. Name and draw the product. (4%)

b. Identify the two reaction types when ethene reacts in the presence of light, and write an equation to illustrate each. Name and draw all possible products. (8%)

Documents

History of Organic Chemistry - MOLEBUS (ALLCHEM) · Web view-CH- b. -CH2--CH3- d. -CH2= Which of the following is a condensed structural diagram for propane? C3H8 CH3-CH2-CH3 d. C-C-C