History of Organic Chemistry - MOLEBUS (ALLCHEM) · Web viewbutane c. pentane cyclopropane d. propane Which of the following compounds is a structural isomer of butane? 2-methylbutane

History of Organic Chemistry

Organic Chemistry Testbank1

History of Organic Chemistry

The first organic chemical to be synthesized in a lab from inorganic chemicals was

a. ethanol

c.methane

b. sugar

d.urea

The first person to synthesis an organic chemical from inorganic chemicals was

a. August Kekulé

c.Friedrich Wöhler

b. John Dalton

d.Raymond LeMieux

The Avitalism@ theory in organic chemistry held that

a.organic chemicals can only be obtained from living organisms

b.organic chemicals can only be obtained from dead organisms

c.organic chemicals can only be obtained from living or dead organisms

d.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 Chemistry

Organic chemicals

a. are all the compounds of carbon including the ionic compounds

b. are all the molecular compounds of carbon except the oxides

c. are all the ionic compounds of carbon including the oxides

d. 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 carbon

b. molecular compounds of carbon

c. non-living substances only

d. 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.C4H7O

b. CO2

d.CCl4

Which is NOT an organic chemical?

c. CH3CHO

c.C2H6O

d. CBr4

d.CO

Which substance is organic?

a. AgCl

c.NH4CN

b. AgOCN

d.(NH2)2CO

Multitude of Organic Chemicals

Which statement is true?

a. Carbon can bond in chains with branches, but cannot form rings

b. 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 bonds

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

Which statement is true?

a. Over 90% of all known compounds are organic

b. Over 90% of all known compounds are inorganic

c. There are about 2 times as many inorganic compounds as organic compounds

d. 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 Series

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

a. 1 hydrogen atom

c.2 hydrogen atoms

b. 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 larger

d. increases by A-CH2" as they get larger

Which of the following is part of a homologous series:

a.CH4, C2H4, C4H8b.CH4, C2H2, C3H6

c.C3H8, C3H6, C3H4d.C2H4, C3H6, C4H8

Which term describes this group of compounds?

chloromethane, chloroethane, 1-chloropropane, 1-chlorobutane

a. aldehydes

c.functional isomers

b. aromatics

d.homologous series

Alkanes/Straight chain alkanes

Alkanes are:

a. organic compounds containing one or more carbon-carbon double bonds

b. special group of unsaturated cyclic hydrocarbons

c. organic compounds containing one or more carbon-carbon triple bonds

d. hydrocarbons that contain only single covalent bonds

How many double covalent bonds are in an alkane?

a. none

c.one

b. two

d.The number varies

How many carbons are in a molecule of hexane?

a. 3

b.4

b. 5

d.6

What is the name of the alkane having five carbons?

a. hexane

c.methane

b. 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?

C

H

C

C

H

2

C

H

C

H

3

C

H

3

a. C3H8

b. CH3-CH2-CH3

d.

c. C-C-C

What is the name of the molecule on the right?

a.

C

H

C

H

2

C

H

2

C

H

3

C

H

3

butane

b. pentane

c. propane

d. tetrane

C

H

3

C

C

H

C

H

2

C

H

3

Cl

C

H

3

Cl


a. butane

b. pentane

c. propane

d. hexane

C

H

3

C

H

2

C

H

C

H

3

O

H

What is the IUPAC name of the compound on the right?

a. butane

b. decane

c. propane

d. pentane

What is the name of the straight chain alkane with 7 carbons?

a. pentane

c.hexene

b. heptane

d.octyne

Branched Alkanes - Nomenclature

Which 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.propyl

What 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-

C

H

3

C

H

C

H

C

H

2

C

H

2

C

H

3

What is the name of the compound on the right?

a. 2,4-diethyl-2-methylhexane

b. 3-ethyl-5,5-dimethylheptane

c. 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-dimethylhexane

b. 2-ethyl-3,3-diemethylhexane

c. 4,4,5-trimethylheptane

d. 3,4,4-trimethylheptane

O

N

H

2

O

H

C

H

3

threonine

O

N

H

2

S

H

cysteine


a. 2,3-dimethylpentane

b. 3,4-dimethylpentane

c. 3,4,4 -trimethylbutane

d. 2,3,4-trimethylbutane

C

C

H

H

C

H

3

C

H

2

C

H

3

n


a. trimethylpentane

b. 2-methyl-3-methyl-4-methylpentane

c. 2,2-dimethyl-3-methylpentane

d. 2,3,4-trimethylpentane

C

C

C

C

C

C

H

H

H

H

H

H

H

H

H

H

H

H


a. 2-ethyl-2,4,5-trimethylpentane

b. 2-ethyl-2,4-dimethylhexane

c. 3,5,5-trimethylheptane

d. 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 butane

b.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.tetramethylpropane

b. 1,1,1,2-tetramethylpropane

d.heptane

Alkenes - Nomenclature

Alkenes are:





Which hydrocarbon contains a double carbon to carbon bond?

a. 1-butene

c.2-methylbutane

b. 1-butyne

d.cyclobutane

Which compound is an alkene?

a. butyne

c.pentane

b. nonene

d.propanone


a. 2-ethyl-3-propyl-1-pentene

b. 2,3-diethyl-4-methyl-1-pentene

c. 3-ethyl-2,4-dimethyl4-hexene

d. 3,4-diethyl-2-methyl-4-pentene


a. 2,3-dimethyl-4-propyl-4-pentene

b. 2,3-dipropyl-1-butene

c. 3,4-dimethyl-2-propyl-1-pentene

d. 4,5,6-trimethyl-4-heptene

What is the IUPAC name of this compound?

a. 1,1-dimethyl-2-butene

b. 2-methyl-3-pentene

c. 4-methyl-2-pentene

d. methylhexane

C

H

2

C

C

C

H

2

C

H

3

C

C

H

3

C

H

3

C

H

3

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

a. 1-methyl-1-pentene

b. 5-methyl-4-pentene

c. 2,3-hexene

d. 2-hexene.

Determine the IUPAC name for the following molecule:

a.2,5-dimethyl-2-hexene

b.2,5-dimethyl-4-hexene

c.2,5-dimethyl-2-heptene

d.2,5-dimethyl-4-heptene

C

H

3

What is the name for the following molecule?

a.2-ethyl-2-pentene

b.4-ethyl-3-pentene

c.3-methyl-3-hexene

d.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 - Nomenclature

Alkynes are:





What is the name of the smallest alkyne?

a. butyne

c.ethyne

b. methyne

d.propyne

C

H

2

C

H

2

C

H

2

C

H

3


a. 4,4-diethyl-2-butyne

b. 4-ethyl-2-hexyne

c. 3-ethyl-4-hexyne

d. 1,1-diethyl-2-butyne

C

H

2

C

H

2

C

H

2

C

H

2

C

H

3


a. 1,6,6,6-tetramethyl-2-pentyne

b. 2,2-dimethyl-4-heptyne

c. 2,2,6-trimethyl-4-hexyne

d. 6,6-dimethyl-3-heptyne

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

a.

C

H

3

C

H

2

C

C

C

H

2

C

H

3

C

H

3

H

c.

b.

C

H

3

C

H

C

H

C

H

C

H

3

C

H

3

d.

C

H

2

C

H

C

H

2

C

H

C

H

3

C

H

3

What is the name of the molecule

C

H

3

C

C

H

?

a.acetylene

c.propyne

b.1-butyne

d.propene

Cycloalkanes, cylcoalkene - Nomenclature


a. ethylbenzene

b. ethylcyclohexane

c. phenylethane

d. propylcyclohexane


a. butylcyclohexane

b. phenylpropane

c. propylbenzene


C

H

2

C

H

C

H

2

C

H

C

H

3

C

H

3

C

H

3


a. ethylcyclopentane

b. pentylcyclopropane

c. propylcylclopentane


C

H

2

C

H

C

H

3

C

H

C

H

3

C

H

2

C

H

3


a. 2-ethylcyclopentene

b. 3-ethylcyclopentene

c. 2-ethyl-2-cyclopentene

d. 5-ethyl-2-cyclopentene


a. 2-methylcyclohexene

b. 3-methylcyclohexene

c. 4-methylcyclohexene

d. 5-methylcyclohexene

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

A

B

C

a.A, B, C

c.C, A, B

b.B, C, A

d.C, B, A

Simple Aromatics - nomenclature

C

H

3

C

H

3


a. 2-butylbenzene

b. butylbenzene

c. phenylbutane

d. propylbenzene


a. butylbenzene

b. 2-pentylbenzene

c. pentylbenzene

d. phenylpentane

C

H

3

C

C

H

C

H

2

C

H

3

Cl

Cl

C

H

3


a. pentylcyclohexane

b. cyclopentylhexane

c. pentylbenzene

d. hexylbenzene

C

H

3

C

H

2

C

H

C

H

2

O

H

C

H

3


a.butylbenzene

b.phenylbutane

c.propylbenzene

d.phenylpropane

Phenyl Branches - nomenclature

C

H

3

C

C

C

H

C

H

2

C

H

3

C

H

2

C

H

3

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

a. 1,1,4-trimethyl-4-phenylbutane

b. 2,4-dimethyl-5-phenylpentane

c. 2,4-dimethyl-2-pentylbenzene

d. 2,4-dimethyl-1-phenylpentane

C

H

2

C

C

H

C

H

2

C

H

3

C

H

C

H

3

C

H

3

C

H

2

C

H

3


a. 2-methyl-3-ethyl-1-phenylbutane

b. 2,3-dimethyl-1-phenylpentane

c. 2,3-dimethyl-1-pentylbenzene

d. 3,4-dimethyl-5-phenylpentane

C

H

2

C

C

H

C

H

2

C

H

2

C

H

C

H

3

C

H

3

C

H

3

C

H

3

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

a.2-pentylbenzene

b.2-phenypentane

c.1 -methyl-1-phenylbutane

d.pentylbenzene

C

H

2

C

H

3

C

H

2

C

H

2

C

C

H

3

C

H

2

C

H

3

C

H

3

How many phenyl groups does the following molecule have?

a.0

c.2

b.1

d.6

Disubstituted benzenes

What is another acceptable name for 1,3-dimethylbenzene?

a.m-dimethylbenzene

c.o-dimethylbenzene

b.n-dimethylbenzene

d.p-dimethylbenzene


a.m-dimethylbenzene

c.o-dimethylbenzene

b.n-dimethylbenzene

d.p-dimethylbenzene


a.m-dimethylbenzene

c.o-dimethylbenzene

b.n-dimethylbenzene

d.p-dimethylbenzene

C

H

3

C

H

C

H

C

H

C

H

3

C

H

3

C

H

3

C

H

3


a. ethylmethylbenzene

b. o-ethylmethylbenzene

c. m-ethylmethylbenzene

d. p-ethylmethylbenzene

What is the name of the compound on the right?

e. diethylbenzene

f. m-diethylbenzene

g. o-diethylbenzene

h. p-diethylbenzene


a. ethylpropylbenzene

b. o-ethylpropylbenzene

c. m-ethylpropylbenzene

d. p-ethylpropylbenzene

What is the IUPAC name for the isomeric compound on the right?

a.1,2-dichlorobenzene

b.1,3-dichlorobenzene

c.2,2-dichlorobenzene

d.2,6-dichlorobenzene

Which of the following molecules is p-ethylmethylbenzene?

a.

b.

c.

d.

Units of Unsaturation/general formulas

What type of hydrocarbon is the compound on the right? CH3-CH2-CH2-CH2-CH2-CH3

a. aliphatic

c.cyclic

b. 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)3CH

A saturated continuous-chain hydrocarbon with seven carbons is _____.

a. cycloheptene

c.heptene

b. heptane

d.heptyne

Which of the following compounds is an unsaturated hydrocarbon?

a. methane

c.nonane

b. propyne

d.ethyl

How many units of unsaturation does the molecular formula C5H8 have?

a. none

c.two

b. one

d.three

How many units of unsaturation does the molecular formula C7H12 have?

a. none

c.two

b. 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.alkynes

b.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 with

a. one ring or one double bond

c.one ring and one double bond

b.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.pentane

b. cyclopropane

d.propane

Which of the following compounds is a structural isomer of butane?

a. 2-methylbutane

c.2,2-dimethylbutane

b. 2-methylpropane

d.2,2-diethylpropane

Which pairs of molecules are structural isomers?

a.cyclohexane and 2,2-dimethylbutane

b.cyclohexene and 3,3-dimethyl-1-butyne

c.methylcyclobutane and 2-pentyne

d.2-methylpentyne and 2-methylpentene

A structural isomer of hexane is _____.

a. benzene

c.cyclohexane

b. 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.3

b. 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 butanoated.propanoic acid and propanal

Structural isomers have _____.

a. the same molecular formula

b. different physical and chemical properties

c. the same elemental composition

d. all of the above

Which of the following pairs of compounds are isomers?

a. propanal and 1-propanol

b. propanoic acid and propyl propanoate

c. propanone and propanal

d. 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.

Halocarbons

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

a. fluorine

c.oxygen

b. 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-ethylpentane

b. 4-chloro-2-ethyl-2-methylpentane d.1-chloro-1,3,3,3-trimethylpentane

C

C

C

C

C

H

H

H

H

H

H

H

H

H

H

H

H


a. 2-dichloro-3-methylpentane

b. 2,2-dichloro-3-methylpentane

c. 4,4-dichloro-3-methylpentane

d. 4,4-dichloro-3,5-dimethylbutane

C

C

C

H

H

H

H

H

H

H

H


a. 2,3-dichloro-2-methylpentane

b. 1,2-dichloro-1,1-dimethylbutane

c. 2,3-chloro-2-methylpentane

d. 3,4-dichloro-4-methylpentane

C

H

3

C

H

2

C

H

2

C

H

3

The correct name for the molecule on the right is:

a.1,4,4-trifluoro-2-bromopentane

b.2-bromo-1,4,4-trifluoropentane

c.2,2,5-trifluoro-4-bromopentane

d.4-bromo-2,2,5-trifluoropentane

Alcohols

C

H

3

C

H

2

C

H

2

C

H

2

C

H

2

C

H

3


a. butanone

b. 2-butanol

c. 2-butanal

d. butyl ether

C

H

3

C

C

H

2

C

H

C

H

2

F

F

F

Br


a. 3-pentanone

b. 3-pentanal

c. 3-pentanol

d. 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- dimethylbutanol

b. 1,1-dimethyl-1-butanol

d.2-methyl-2-pentanol

Ethers

Which molecule is an ether?

a.

C

H

3

C

H

C

H

2

C

H

2

C

H

3

O

H

c.

C

H

3

C

O

C

H

2

C

H

3

O

b.

C

H

3

C

H

O

C

H

2

C

H

3

C

H

3

d.

C

H

2

C

O

H

O

C

H

3

Which of the following is an ether?

a.

C

H

3

C

H

2

C

H

2

C

H

2

C

O

H

O

c.

C

H

3

C

H

2

O

C

H

3

b.

C

H

3

C

H

2

C

H

2

C

C

H

3

O

d.

C

H

3

C

H

2

C

H

2

C

H

O

C

H

3

O

C

H

2

C

H

2

C

H

3


a. butanal

b. methylpropyl ether

c. butanone

d. methyl propanoate

C

H

2

O

C

H

2

C

H

2

C

H

3

C

H

3


a.pentanal

b.ethylpropyl ether

c.pentanone

d.ethyl propanoate

Aldehydes

Which molecule is an aldehyde?

a.

O

C

C

H

2

C

H

2

C

H

3

C

H

3

c.

C

H

3

C

O

C

H

2

C

H

3

O

b.

C

H

3

C

H

O

C

H

2

C

H

3

C

H

3

d.

H

C

C

H

2

C

H

2

C

H

3

O

Which of the following is an aldehyde?

a.

C

H

3

C

H

2

C

H

2

C

H

2

C

O

H

O

c.

C

H

3

C

H

2

O

C

H

3

b.

C

H

3

C

H

2

C

H

2

C

C

H

3

O

d.

C

H

3

C

H

2

C

H

2

C

H

O

C

H

C

H

2

C

H

2

C

H

3

O


a. butanal

b. 1-butanone

c. butanoic acid

d. propanal

C

H

C

H

2

C

H

2

C

H

2

O

C

H

3


a. butanal

b. 1-butanone

c. butanoic acid

d. propanal


a. butanone

c.ethane

b. ethanol

d.pentanal


a.butanal

b. ethanone

c.ethanol

d.pentanoic acid

Ketones

O


a. ethylpropyl ether

b. 3-hexanal

c. 3-hexanone

d. methyl butanoate

O


a. diethyl ether

b. 2-pentanone

c. 3-pentanone

d. 3-pentanal

Which of the following is a ketone?

a.

C

H

3

C

H

2

C

H

2

C

H

2

C

O

H

O

c.

C

H

3

C

H

2

O

C

H

3

b.

C

H

3

C

H

2

C

H

2

C

C

H

3

O

d.

C

H

3

C

H

2

C

H

2

C

H

O

Which condensed structural formula represents a ketone?

a.CH3CH2CH2OH

c.CH3COCH3

b.CH3CH2CHO

d.CH3CH2COOH

Carboxylic Acids

Cl

Cl


a. butanone

b. ethanoic acid

c. methy propanoate

d. propanoic acid

O

H

O


a. butanal

b. butanoic acid

c. methy propanoate

d. propanoic acid

C

H

3

C

H

2

O

C

O

H


a.pentanal

b.pentanoic acid

c.methy butanoate

d.pentanone

Esters

O

H

O


a. butyl ethanoate

b. ethyl propanoate

c. ethyl butanoate

d. propyl ethanoate

O

O


a.ethyl methanoate

b.methyl ethanoate

c.ethanoic acid

d.propanoic acid

C

H

2

C

H

2

C

H

2

C

O

H

O

C

H

3


a.

O

O

ethyl propanoate

b. methyl butanoate

c. butyl methanoate

d. methyl propanoate

Trivial Names

C

H

3


a. acetylene

b. formaldehyde

c. phenol

d. toluene

O

H


a. acetylene

b. formaldehyde

c. phenol

d. 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 reactions

b.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 points

d.Crude oil from different sources, when distilled in a fractionating tower, will yield the same percent of gasoline

Which compound in crude oil will be the first to evaporate relative to the other hydrocarbons listed?

a. decane

c.heptane

b. nonane

d.octane

What is not a source of raw materials for petrochemical industries?

a. coal deposits

c.crude oil

b. 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.lignite

b. bituminous

d.peat

Which process involves the conversion of once living organic matter to fossil fuels?

a. carbonization

c.combustion

b. nuclear fusion

d..photosynthesis

Shapes of molecules

The bonding shape around every carbon in propane is

a. bent

c.tetrahedral

b. linear

d.trigonal planar

What is the shape of a methane molecule?

a. bent

c.pyramidal

b. linear

d.tetrahedral

The bonding shape around both carbons in ethyne is

a. bent lineartetrahedraltrigonal 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 planar

b. linear

c. tetrahedral

d. 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.propanal

b. propanone

d.propane

Which substance would be least soluble in water?

a. propanoic acid

c.propanal

b. propanone

d.propane

Which substance is immiscible with water?

a. 2-butanol

c.ethanal

b. 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. C3H7OH

In which of the following compounds is hexane most likely to dissolve?

a. acetic acid

c.ethyl alcohol

b. 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-dimethylpentane

b. 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 bonding

b. 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.isomerism

b. 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 weight

b. similar boiling and melting points primarily because they have similar polarities

c. similar boiling and melting points primarily because they are nearly equal in stability

d. 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.4

b.3

d.5

What is the physical state of the smallest alkanes (C1-C4) at room temperature?

a. gas

c.solid

b. liquid

d.gas or liquid

Intermolecular Forces

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

a. 1-pentanol

c.pentanal

b. 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.propanal

b. propanoic acid

d.propanol

Hydrogen bonding is most noticeable in

a. alkanes

c.esters

b. 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 Bonding

How many valence electrons surround a carbon atom?

a. 1

c.3

b. 2

d.4

How many covalent bonds does each carbon atom participate in an organic compound?

a. 1

c.3

b. 2

d.4

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

a.

C

C

H

H

c.

C

C

H

H

c.

C

C

H

H

d.

C

C

H

H

Benzene Bonding

What compound is the simplest of the arenes?

a. benzene

c.ethyne

b. ethene

d.methane

Which of the following molecules does NOT have delocalized electrons?

a. benzene

c.cyclohexane

b. 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 bonds

b. all carbon-carbon double bonds

c. neither double nor single bonds

d. easily broken in chemical reactions.

Which chemical has delocalized electrons?

a.

C

H

3

C

C

H

b.

C

H

3

C

H

3

C

H

2

c.

d.

What distinguishes benzene and benzene compounds from other organic compounds?

a. benzene and benzene compounds are planar molecules

b. carbon atoms in benzene have 120 bond angles

c. carbon atoms in the benzene ring have just three bonding electrons

d. 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.C3H70H

An arrangement of several atoms which gives characteristic properties to an organic molecule is known as a(an)

a. carboxyl group

c.group

b. 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 group

b. its level of saturation

d.its solubility in water

In the general formula for alcohols, R-OH, the "R' represents

a. radon

c.the functional group

b. CH3 only

d.an alkyl group

The functional group for aldehydes is:

a. hydroxyl

c.carboxyl

b. carbonyl

d.ester

The functional group for ketones is:

c. hydroxyl

c.carboxyl

d. carbonyl

d.ester

The functional group for alcohols is:

e. hydroxyl

c.carboxyl

f. carbonyl

d.ester

The functional group for carboxylic acids is:

g. hydroxyl

c.carboxyl

h. carbonyl

d.ester

Which compound contains the functional group called hydroxyl?

a. CH3OH

c.HCOOH

b. H2CO

d.NH4CH3COO

The functional group for alcohols is

a. hydroxyl

c.carboxyl

b. 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.fusion

b. photosynthesis

d.respiration

Cracking/Reforming

Which reaction type uses ethene and low molecular weight hydrocarbons and converts them into gasoline grade hydrocarbons?

a. cracking

c.esterification

b. 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.esterification

b. hydrogenation

d.cracking

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

a. elimination

c.esterification

b. reforming

d.substitution

n-decane + H2 ( butane + _______

ADVANCE \u19

ADVANCE \d19Substitution

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

a. 1,3-dibromobenzene

c.1,2,3,4-tetrabromobenzene

b. 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-tetrachlorobenzene

b. p-dichlorobenzene

d.hydrogen chloride

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

I.H2II.Cl2III.C2H4IV.C2H6

a.I and III

c.I and IV

b.II and III

d.II and IV

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

I.Br2II.HBrIII.C2H6 IV.C2H4

a.I and III

c.I and IV

b.II and III

d.II and IV

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

a. an alkane

c.an alkyne

b.an alkene

d.a ketone

Based on the generalizations for reaction types, butane and fluorine gases react by

a. addition

c.combustion

b. esterification

d.substitution

Short answer:

propane + 1 mol chlorine

pentane + 1 mol bromine

benzene + 2 mol bromine

m-dimethylbenzene + chlorine

butane + 2 mol bromine

pentane + Br2

hexane + chlorine ADVANCE \d3ADVANCE \u3

Addition

Which IS a product of the reaction between 2-butene and 1 mol of chlorine?

a. 1,2-dichlorobutane

c.1,3-dichlorobutane

b. 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.hydrogen

b. 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-dichloropentane

b. 1,2-dichloropentane

d.2,2-dichloropentane

What type of reaction is C2H4+ H2 (C2H6?

a. addition

c.condensation

b. substitution

d.esterification

Which equation represents an addition reaction?

a. CH3CH3 + Cl2 (CH3CH2Cl + HCl

b. CH2CH2 + Cl2 (CH2ClCH2Cl

c. CH3CH2Cl + OHB ( CH2CH2 + H2O + ClB

d. CH2CH2 + CH3CH3 ((CH3)2CHCH3

How many products will result when 1-butene reacts with water?

a. 1

c.3

b. 2

d.4

How many products will result when 2-butene reacts with water?

a. 1

c.3

b. 2

d.4

Which organic reactant will produce 3-chloropentane when reacted with hydrogen chloride?

a. pentane

c.2-pentene

b. 1-pentene

d.2-pentyne

Short answer

2-pentyne + excess HCl

2-pentyne + 2 mol HCl

2-butyne + 2 mol HBr

1-butyne + 2 mol HCl

3-octene + hydrogen iodide

1-pentene + water

1-butene + water

3-heptene + water

4-methyl-1-butyne + 1 mol hydrogen

Esterfication

Which 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 acid

b. 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.methanol

b. sodium hydroxide

d.sulfuric acid

What is the organic product of the reaction of methanol and ethanoic acid?

a. propanone

c.ethyl methanoate

b. propanal

d.methyl ethanoate

Short answer

ethanoic acid + 1-pentanol

propanol + butanoic acid

methanoic acid + 1-pentanol

1-butanol + _________________ ( butyl propanoate

Hydrocarbon Combustion

When hydrocarbons are burned completely, which product is always formed?

a. amorphous graphite

c.limewater

b. carbon dioxide

d.methane

Short answer

2-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

Elimination

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

a. 2-fluoropropane

c.ethanoic acid

b. 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.pentane

Which reaction will not produce an alkene?

a. 2-chlorohexane is heated with sodium hydroxide

b. 2-pentyne and hydrogen are mixed in the presence of a platinum catalyst

c. 1-propanol is warmed with butanoic acid in the presence of a strong acid

d. 3-propanol is warmed in the presence of a strong acid

Short answer

2-chlorobutane + hydroxide ions

2-chlorobutane + sodium hydroxide

2-pentanol is warmed in the presence of a strong acid

ethanol

H

SO

2

4

¾

®

¾

¾

3-heptanol

H

SO

2

4

¾

®

¾

¾

ADVANCE \d3

ADVANCE \u3

Reaction type: _______________________

Identifying Polymerization

Identify the reaction type:

C

C

O

H

O

O

O

H

+

C

H

2

C

H

2

O

H

O

H

C

C

O

O

O

O

C

H

2

C

H

2

n

n

n

+

O

H

2

n

a. addition polymerization

c.condesation polymerization

b. esterification

d.hydrocarbon combustion

Identify the reaction type:

C

C

C

H

3

H

H

H

n

C

C

H

H

H

C

H

3

n

a. addition polymerization

c.condesation polymerization

b. esterification

d.hydrocarbon combustion

What monomer was used to produce the polymer:

C

H

3

C

H

3

C

H

3

. . .

. . .

a.

C

C

H

C

H

3

H

C

H

3

b.

C

C

H

C

H

3

H

H

c.

C

C

C

H

3

C

H

3

H

C

H

3

d.

C

C

C

H

3

H

C

H

3

H

C

H

3

Condensation Polymerization

Which polymer was produced by condensation polymerization?

a.

O

O

C

H

3

C

H

3

O

O

n

b.

C

H

3

C

H

3

C

H

3

C

H

3

C

H

3

. . . .

. . . .

c.

C

H

C

H

C

H

3

n

d.

C

C

C

H

3

C

H

3

H

H

n

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

O

N

H

2

C

H

3

glycine

O

N

H

2

cysteine

O

N

H

2

S

H

Threonine

O

N

H

2

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)

C

H

3

C

H

2

C

C

C

H

2

C

H

3

C

H

3

H

Addition Polymerization

Which substance will undergo addition polymerization?

a. 1-propanol

c.propanal

b. propanone

d.propene

Which monomer will produce the polymer on the right?

a. 1-pentene

b. 2-pentene

c. ethylmethylethane

d. pentane

Which synthetic polymer is the product of addition polymerization?

a. cellulose

c.ribonucleic acid (RNA)

b. protein

d.teflon

Short answer

addition polymerization reaction with 1-pentene

addition polymerization reaction with 1-butene

n 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%)

� EMBED ACD.ChemSketch.20 ��




�

















































� EMBED WP8Doc ��





+

H

2

C

H

3

C

H

C

H

C

H

2

C

H

2

C

H

3

C

H

3

C

H

2

C

H

2

C

H

2

C

H

2

C

H

3

C

H

2

C

H

2

C

H

2

C

H

3

C

H

2

C

H

C

H

3

C

H

C

H

3

C

H

2

C

H

3

C

H

C

H

2

C

H

2

C

H

3

C

H

3

C

H

2

C

H

C

H

2

C

H

C

H

3

C

H

3

C

H

3

C

H

3

C

H

3

Cl

Cl

C

H

3

C

C

H

C

H

2

C

H

3

Cl

Cl

C

H

3

C

H

3

C

C

H

2

C

H

C

H

2

F

F

F

Br

C

H

3

C

H

2

C

H

C

H

2

O

H

C

H

3

C

H

3

O

C

H

2

C

H

2

C

H

3

+

H

2

C

H

2

C

C

C

H

2

C

H

3

C

C

H

3

C

H

3

C

H

3

C

C

C

C

C

C

H

H

H

H

H

H

H

H

H

H

H

H

C

H

2

C

C

H

C

H

2

C

H

3

C

H

C

H

3

C

H

3

C

H

2

C

H

3

C

H

2

C

C

H

C

H

2

C

H

2

C

H

C

H

3

C

H

3

C

H

3

C

H

3

C

H

2

C

H

3

C

H

2

C

H

2

C

C

H

3

C

H

2

C

H

3

C

H

3

C

H

3

C

H

C

H

C

H

C

H

3

C

H

3

C

H

3

C

H

3

C

H

3

C

H

2

C

H

2

C

H

3

C

H

3

C

H

2

C

H

2

C

H

2

C

H

2

C

H

3

C

C

C

C

C

H

H

H

H

H

H

H

H

H

H

H

H

C

H

3

C

H

2

C

H

C

H

3

O

H

C

H

2

O

C

H

2

C

H

2

C

H

3

C

H

3

C

H

C

H

2

C

H

2

C

H

3

O

C

H

C

H

2

C

H

2

C

H

2

O

C

H

3

O

O

O

H

O

C

H

3

C

C

H

C

H

2

C

H

3

Cl

C

H

3

Cl

O

H

O

O

O

C

H

2

C

H

2

C

H

2

C

O

H

O

C

H

3

C

H

3

C

H

2

O

C

O

H

O

O

C

H

3

O

H

C

C

H

H

C

H

3

C

H

2

C

H

3

n

O

N

H

2

O

H

C

H

3

threonine

O

N

H

2

S

H

cysteine

C

C

C

H

H

H

H

H

H

H

H

C

H

3

C

C

C

H

C

H

2

C

H

3

C

H

2

C

H

3

_1105106259.unknown

_1105105802.unknown

_1105104811.unknown

_1105099356.unknown

_1105099280.unknown

Documents

History of Organic Chemistry - MOLEBUS (ALLCHEM) · Web viewbutane c. pentane cyclopropane d. propane Which of the following compounds is a structural isomer of butane? 2-methylbutane