Deck 19: Organic Chemistry I

Question 1

Name the compound CH₃C(CH₃)₂CH₂CH₃.

A)2-isopropylpropane
B)1-methyl-2-propylethane
C)2,2-dimethylbutane
D)1,1-dimethylbutane
E)Hexane

Answer 1

2,2-dimethylbutane

Question 2

Name the following compound.

A)1-iodo-toluene
B)1-methyl-2-iodobenzene
C)m-iodobenzene
D)2-iodo-3-methylbenzene
E)m-toluene

Answer 2

1-iodo-toluene

Question 3

Name the compound CH₃C(CH₃)₂C(CH₃)(CH₂CH₃)CH(CH₃)₂.

A)3,4-dimethyl-3-tert-butylpentane
B)3-isopropyl-3,4,4-trimethylpenatane
C)3-ethyl-2,2,3,4-tetramethylpentane
D)Undecane
E)3-ethyl-2,3,4,4-tetramethylpentane

Answer 3

3-ethyl-2,2,3,4-tetramethylpentane

Question 4

Name the compound CH₃CH(CH₃)CH(CH₂CH₃)C(CH₃)₃.

A)2,4,4-trimethyl-3-ethylpentane
B)2,2,4-trimethyl-3-ethylpentane
C)Decane
D)1,2-tetramethylpentane
E)2,2-dimethyl-3-ethyl-4-methylpentane

Question 5

All of the following are saturated hydrocarbons except

A)C₄H₁₀.
B)C₃H₄.
C)C₅H₁₂.
D)C₄H₆.
E)C₃H₈.

Question 6

Name the compound C(CH₃)₄.

A)2-methylbutane
B)pentane
C)2,2-dimethylpropane
D)Isopropylmethane
E)Isobutylmethane

Question 7

Heptane,with the formula,C₇H₁₆,can have how many isomeric structures?

A)4
B)5
C)6
D)7
E)9

Question 8

Name the following compound.

A)1,1-dichloro-5-methylcyclohexane
B)1-methyl-3,3-dichlorocyclohexane
C)1,1-dichloro-3-methylcyclohexane
D)Dichlorocyclohexane-3-methyl
E)1-methyl-5,5-dichlorocyclohexane

Question 9

Name the compound (CH₃CH₂)₂CHCH=CHCH₃.

A)Diethylbutene
B)3-ethyl-4-hexene
C)4,4-diethyl-2-butene
D)4-ethyl-2-hexene
E)Ethylhexene

Question 10

Name the compound CH₂=CHC(CH₃)CH(CH₃)₂.

Question 11

Which of the following has the highest boiling point?

A)C₃H₈
B)CH₃(CH₂)₇CH₃
C)CH₃(CH₂)₃CH₃
D)CH₃(CH₂)₄CH₃
E)CH₃(CH₂)₅CH₃

Question 12

Name the following compound.

A)Cyclopentane-1-chloro-3-methyl
B)1-methyl-4-chlorocyclopentane
C)1-methyl-3-chlorocyclopentane
D)1-chloro-4-methylcyclopentane
E)1-chloro-3-methylcyclopentane

Question 13

Name the compound (CH₃)₂CHCCCH₃.

Question 14

Name the compound CH₃CH(CH₂CH₃)CH(CH₂CH₃)CH(CH₃)CH(CH₃)₂.

A)Dodecane
B)2,3-diethyl-4,5-dimethylhexane
C)2,3-dimethyl-4,5-diethylhexane
D)2-ethyl-3-ethyl-4-methyl-5-methylhexane
E)2,3-diethy-4-isopropylpentane

Question 15

Name the following compound.

Question 16

Name the following compound.

Question 17

Name the following compound.

A)1-tert-butyl-4-ethyl-5-methylbutane
B)Undecane
C)1,1,1,4-tetramethyl-3-ethylpentane
D)3-ethyl-2,5,5-trimethylhexane
E)4-ethyl-2,2,5-trimethylhexane

Question 18

Which of the following could be a cycloalkane?

A)C₃H₈
B)C₅H₁₂
C)C₆H₁₄
D)C₆H₁₂
E)C₄H₁₀

Question 19

Name the following compound.

Question 20

The compound (CH₃)₃CCH₂CH(CH₃)₂ is

A)named as a pentane but is an isomer of heptane.
B)named as a pentane but is an isomer of octane.
C)named as a hexane but is an isomer of octane.
D)named as a pentane but is an isomer of hexane.
E)named as a butane but is an isomer of octane.

Question 21

Consider the compound below. Which of the following is true?

A)The compound has geometric isomers.
B)The compound is not chiral.
C)The compound exists as 3 stereoisomers.
D)The compound is chiral and does not have geometric isomers.
E)The compound is chiral.

Question 22

Which of the following have a cis configuration?

A)2
B)1 and 2
C)2 and 4
D)1,2,and 4
E)1 and 4

Question 23

Which of the following compounds exist as geometric isomers?

A)1,2,3,and 4
B)2 and 4
C)1 and 3
D)1,2,and 4
E)3 and 4

Question 24

The alkene CH₃CH=CHCH₂CH₃ cannot exist as cis and trans isomers.

Question 25

Which of the following compounds has a chiral center?

A)CH₃CH₂CH(NH₂)COOH
B)(CH₃) ₂C(NH₂)COOH
C)CH₃CHCH(Cl)
D)NH₂CH₂COOH
E)C(CH₃)₄

Question 26

Of the following five alkanes,which has the highest boiling point?

A)CH₃CH(CH₃)CH(CH₃)CH₂CH₃
B)CH₃CH(CH₃)(CH₂)₃CH₃
C)C₃H₈
D)CH₃CH(CH₃)(CH₂)₃CH₃
E)CH₃(CH₂)₄CH₃

Question 27

Which of the following have a trans configuration?

A)1,3,and 4
B)3
C)1,2,and 3
D)1 and 3
E)1,2,3,and 4

Question 28

Which of the following is optically active?

A)NH₂CH(CH₃)COOH
B)(CH₃)₂C(NH₂)COOH
C)CH₃CHCH(Cl)
D)C(CH₃)₄
E)NH₂CH₂COOH

Question 29

The compound 1-chloro-1-pentene

A)can exist as cis and trans isomers.
B)has the formula C₅H₁₁Cl.
C)cannot exist as cis and trans isomers.
D)is an alkyne.
E)has 3 structural isomers.

Question 30

How many of the structural isomers of C₆H₁₄ have tertiary hydrogens?

A)5
B)2
C)1
D)3
E)4

Question 31

A racemic mixture is an equal mixture of enantiomers and therefore is optically active.

Question 32

How many of the structural isomers of C₆H₁₄ have only primary and tertiary hydrogens?

A)1
B)2
C)3
D)4
E)5

Question 33

The compound 2-chloro-1-pentene

A)has the formula C₅H₁₁Cl.
B)is an alkyne.
C)cannot exist as cis and trans isomers.
D)can exist as cis and trans isomers.
E)has 3 structural isomers.

Question 34

Name the following compound.

A)cis-1,2-dichloro-1-butene
B)Dichlorobutene
C)cis-2-ethyl-1,2-dichloroethene
D)trans-1,2-dichloro-1-butene
E)cis-1,2-dichloro-2-ethylethene

Question 35

Consider a molecule of molecular formula C₁₀H₁₆.What total number of rings plus $\pi$ bonds are present in the molecule?

A)2
B)1
C)3
D)4
E)0

Question 36

How many of the structural isomers of C₆H₁₄ have only primary and secondary hydrogens?

A)2
B)1
C)5
D)4
E)3

Question 37

Consider a molecule of molecular formula C₁₀H₁₈.What total number of rings plus $\pi$ bonds are present in the molecule?

A)3
B)1
C)4
D)0
E)2

Question 38

All of the following are structural isomers of C₆H₁₄ except

A)CH₃(CH₂)₄CH₃
B)CH₃CH₂C(CH₃)₃
C)(CH₃)₂CHCH(CH₃)₂
D)CH₃(CH₂)₂CH(CH₃)₂
E)(CH₃)₂CHCH₂CH₃

Question 39

Name the following compound.

A)cis-2-pentene
B)trans-1-methyl-1-butene
C)Ethylmethylethene
D)trans-1-ethyl-1-propene
E)trans-2-pentene

Question 40

Enantiomers have identical chemical properties,except when they react with other chiral compounds.

Question 41

What major product(s)is (are)obtained from the following reaction?

A)ortho-nitroaniline and para-nitroaniline
B)para-nitroaniline
C)meta-nitroaniline
D)ortho-,meta-,and para-nitroaniline
E)ortho-nitroaniline

Question 42

When 2-methyl-1-butene reacts with HBr,the reaction occurs in two steps.Draw the structure of the intermediate.(Hint: Intermediate carbocations are most stable when formed at tertiary carbons.)

Question 43

The product of the reaction of 2-butene with Cl₂ is

A)3,3-dichlorobutane.
B)2,3-dichlorobutane.
C)butane.
D)2-chlorobutane.
E)2,2-dichlorobutane.

Question 44

How many different monochlorination products are formed when n-butane reacts with chlorine gas under the influence of UV light?

A)5
B)1
C)3
D)2
E)4

Question 45

Why do alkanes not react with boiling nitric acid?

Question 46

Which of the following pairs react?

A)CH₄(g)and KMnO₄(aq)
B)CH₄(g)and NaOH(aq)
C)CH₄(g)and Cl₂(g)
D)CH₄(g)and HNO₃(l)
E)CH₄(g)and H₂SO₄(l)

Question 47

With which of the following do alkanes react?

A)Boiling nitric acid
B)The strong oxidizing agent KMnO₄
C)Boiling aqueous sodium hydroxide to give alcohols
D)Concentrated sulfuric acid
E)Oxygen to give carbon dioxide and water

Question 48

When 2-methyl-1-butene reacts with HBr,what are the two products formed?

Question 49

Which of the following undergo nitration more slowly than benzene?

A)3 and 4
B)1 and 2
C)2 and 3
D)1,4,and 5
E)1 and 5

Question 50

Which of the following undergo nitration faster than benzene?

A)4 and 5
B)2,3,and 5
C)1 and 2
D)3 and 4
E)1,4,and 5

Question 51

Which of the following forms ortho- and meta-products upon nitration?

A)Phenol
B)Benzoic acid
C)Nitrobenzene
D)Cyanobenzene (benzonitrile)

Question 52

When 2-methyl-1-butene reacts with HBr,the reaction occurs in two steps.The attacking agent in the first step is __________.

Question 53

How many different monochlorination products are formed when 2-methylpentane reacts with chlorine gas under the influence of UV light?

A)5
B)1
C)2
D)3
E)4

Question 54

The most characteristic reaction of alkenes is

A)addition
B)substitution
C)dehydrogenation
D)dimerization
E)elimination

Question 55

The product of the reaction of 2-butene with HBr is

A)1-bromobutane.
B)2-bromo-2-butene.
C)butane.
D)2-bromo-1-butene.
E)2-bromobutane.

Question 56

When 2-methyl-1-butene reacts with HBr,the reaction occurs in two steps.What is the major product? (Hint: Intermediate carbocations are most stable when formed at tertiary carbons.)

Question 57

Which of the following forms a meta-product upon nitration?

A)Benzoic acid
B)Aaniline
C)Phenol
D)Chlorobenzene

Question 58

Arenes undergo predominantly addition reactions.

Question 59

What type of reaction is the reaction of ethene with bromine water resulting in the formation of 1,2-bromoethane?

A)Redox reaction.
B)Nucleophilic reaction.
C)Substitution reaction.
D)Oxidation reaction.

Question 60

The product of the hydrogenation of cis-2-butene is

A)2-butyne
B)trans-butane
C)cis-butane
D)trans-2-butane
E)butane

Question 61

How many monobrominated products are predicted theoretically from the following reaction?

A)5
B)3
C)4
D)6
E)2

Question 62

What major product(s)is (are)obtained from the following reaction?

A)1,4-dinitrobenzene
B)1,2-,1,3-,and 1,4-dinitrobenzene
C)1,3-dinitrobenzene
D)1,2-dinitrobenzene and 1,4-dinitrobenzene
E)1,2-dinitrobenzene

Question 63

A dichlorobenzene reacts with HNO₃/H₂SO₄ and produces three mononitrated products.Identify the initial dichlorobenzene.

Question 64

What major product(s)is (are)predicted from the following reaction?

A)1-chloro-1-phenylethane
B)meta-chloroethylbenzene
C)ortho- and para-chloroethylbenzene
D)ortho-chloroethylbenzene
E)para-chloroethylbenzene

Question 65

How many products are predicted theoretically from the following reaction?

A)5
B)3
C)1
D)4
E)2

Question 66

What is the product of benzoic acid after it is treated with nitric acid and concentrated sulfuric acid?

A)ortho-nitrobenzoic acid
B)para -nitrobenzoic acid
C)para-nitrobenzoic acid
D)ortho- and para-nitrobenzoic acids

Question 67

What major product(s)is (are)obtained from the following reaction?

A)1,3,5-trinitrobenzene
B)1,2,3-trinitrobenzene
C)1,2,3,5-tetranitrobenzene
D)1,3,4,5-tetranitrobenzene
E)1,3,4-trinitrobenzene

Question 68

How many products are predicted for the reaction below?

A)1
B)2
C)3
D)4
E)No reaction occurs.

Question 69

Consider the reaction of ethene with bromine water to produce 1,2-dibromoethane.Which of the following statements is correct regarding this reaction?

A)This reaction is a nucleophilic reaction.
B)This reaction is a substitution reaction.
C)A negatively charged intermediate is involved in this reaction.
D)A cyclic bromonium ion is an intermediate in this reaction.

Question 70

Fill in the missing reactants and products in the reaction scheme below.

Question 71

What major product(s)is (are)predicted from the following reaction?

A)ortho-dibromobenzene and para-dibromobenzene
B)ortho-dibromobenzene
C)ortho-,meta-,and para-dibromobenzene
D)meta-dibromobenzene
E)para-dibromobenzene

Question 72

For the compounds below,which statement is true?

A)Compound 1 is chiral.
B)Compound 2 is chiral.
C)Compounds 1 and 2 are chiral.
D)Compounds 1 and 2 are identical.

Question 73

A dichlorobenzene reacts with HNO₃/H₂SO₄ and produces one mononitrated product.Identify the initial dichlorobenzene.

Question 74

The most common reaction of benzene is addition.

Question 75

Which of the following species is likely to attack benzene and result in substitution?

A)NH₃
B)FeBr₄ ^-
C)OH^-
D)HCl
E)NO₂⁺

Question 76

A mixture of nitric acid and concentrated sulfuric acid is used to convert benzene to nitrobenzene.The nitrating agent in this reaction is

A)HNO₃
B)NO₂^-
C)NO₂⁺
D)NO₃^-

Question 77

How many products are predicted for the reaction below?

A)4
B)No reaction occurs.
C)3
D)1
E)2

Question 78

For the compounds below,which statement is true?

A)Compound 1 is chiral.
B)Compounds 1 and 2 are chiral.
C)Compounds 1 and 2 are geometric isomers.
D)Compounds 1 and 2 are identical.

Question 79

What major product(s)is (are)predicted from the following reaction?

A)None,the ring is deactivated and no reaction occurs.
B)2,4-dibromonitrobenzene
C)3,4-dibromonitrobenzene
D)1,4-dibromobenzene
E)1,2,3-tribromonitrobenzene

Question 80

Alkanes undergo substitution by a radical chain mechanism,even though they are very unreactive?