Deck 19: Organic Chemistry I

Question 1

Name the compound C(CH₃)₄.

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

Answer 1

2,2-dimethylpropane

Question 2

Name the compound (CH₃)₂CHCCCH₃.

Answer 2

4-methyl-2-pentyne

Question 3

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

Answer 3

4-ethyl-2,2,5-trimethylhexane

Question 4

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 5

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 6

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

Question 7

Name the compound CH₃C(CH₃)₂CH₂CH₃.

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

Question 8

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 9

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 10

All of the following are saturated hydrocarbons except

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

Question 11

Name the following compound.

Question 12

Which of the following could be a cycloalkane?

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

Question 13

Name the following compound.

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

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)1,1-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 18

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

Question 19

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 20

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

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

Question 21

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 22

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 23

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 24

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 25

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 26

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 27

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

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

Question 28

A racemic mixture is an equal mixture of enantiomers and therefore is optically active.True or false?

Question 29

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

Question 30

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 31

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 32

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 33

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 34

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 35

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 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

Enantiomers have identical chemical properties,except when they react with other chiral compounds.True or false?

Question 38

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 39

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 40

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 41

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 42

The most characteristic reaction of alkenes is

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

Question 43

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 44

Why do alkanes not react with boiling nitric acid?

Question 45

Arenes undergo predominantly addition reactions.True or false?

Question 46

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 47

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 48

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 49

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 50

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 51

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 52

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 53

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 54

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 55

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

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 ortho- and meta-products upon nitration?

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

Question 58

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

Question 59

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 60

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

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

Question 61

Which of the following undergoes electrophilic reactions?

A)ethanol
B)butane
C)2-propene
D)chloroethane

Question 62

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

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

Question 63

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 64

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

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

Question 65

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 66

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 67

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

Question 68

For the compounds below,which statement is true? 1 2

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 69

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 70

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 71

How many products are predicted for the reaction below?

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

Question 72

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 73

How many products are predicted for the reaction below?

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

Question 74

The most common reaction of benzene is addition.True or false?

Question 75

For the compounds below,which statement is true? 1 2

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 76

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

Question 77

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

Question 78

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 79

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

Question 80

How many products are predicted theoretically from the following reaction?

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