Question 1

Which alkene would you expect to be the major product of the following dehydration?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 2

Dehydrohalogenation of tert-pentyl bromide at higher temperatures will produce 2-methyl-1-butene as the chief product when:

Accepted Answer

A) CH3COONa is employed as the base. 
B) KOH/C2H5OH is employed as the base 
C) CH3CH2ONa/CH3CH2OH is employed as the base. 
D) (CH3)3COK/(CH3)3COH is employed as the base. 
E) any base is used,as long as the temperature is sufficiently high. 
A) CH3COONa is employed as the base. 
B) KOH/C2H5OH is employed as the base 
C) CH3CH2ONa/CH3CH2OH is employed as the base. 
D) (CH3)3COK/(CH3)3COH is employed as the base. 
E) any base is used,as long as the temperature is sufficiently high.

Question 3

Which reaction conditions would not yield 2-butyne from 1-propyne?

Accepted Answer

A)    
B)    
C)    
D)    
E) More than one of these choices. 
A)    
B)    
C)    
D)    
E) More than one of these choices.

Question 4

What would be the major product(s)of the following reaction?

Accepted Answer

A) I and II 
B) I,II,and III 
C) III 
D) IV 
E) None of these choices. 
A) I and II 
B) I,II,and III 
C) III 
D) IV 
E) None of these choices.

Question 5

Carbocations are frequent intermediates in acidic reactions of alkenes,alcohols,etc.What do carbocations usually do? They may:

Accepted Answer

A) rearrange to a more stable carbocation. 
B) lose a proton to form an alkene. 
C) combine with a nucleophile. 
D) react with an alkene to form a larger carbocation. 
E) do all of these choices. 
A) rearrange to a more stable carbocation. 
B) lose a proton to form an alkene. 
C) combine with a nucleophile. 
D) react with an alkene to form a larger carbocation. 
E) do all of these choices.

Question 6

What is the major product for the following reaction sequence?

Accepted Answer

A)    
B)    
C)    
D)    
E)    
A)    
B)    
C)    
D)    
E)

Question 7

By analyzing the starting material and the product(s),the following reaction is an example of what type of mechanism?

Accepted Answer

A) SN1 
B) SN2 
C) E1 
D) E2 
E) None of these choices. 
A) SN1 
B) SN2 
C) E1 
D) E2 
E) None of these choices.

Question 8

What is the major product for the following reaction sequence?

Accepted Answer

A)    
B)    
C)    
D)    
E) None of these choices. 
A)    
B)    
C)    
D)    
E) None of these choices.

Question 9

Predict the product(s)for the following reaction sequence.

Accepted Answer

A)    
B)    
C)    
D)    
E) None of these choices. 
A)    
B)    
C)    
D)    
E) None of these choices.

Question 10

Catalytic hydrogenation utilizing palladium,platinum or nickel proceeds through a process known as ___ catalysis as the metal catalyst is not soluble in the reaction mixture.

Accepted Answer

The answer of Catalytic hydrogenation utilizing palladium,platinum or nickel proceeds...

Question 11

The product(s)for the following reaction would mainly be dictated by which mechanism?

Accepted Answer

A) SN1 
B) SN2 
C) E1 
D) E2 
E) None of these choices. 
A) SN1 
B) SN2 
C) E1 
D) E2 
E) None of these choices.

Question 12

What is the major product of the reaction of the following reaction?

Accepted Answer

A)    
B)    
C)    
D)    
E) None of these choices. 
A)    
B)    
C)    
D)    
E) None of these choices.

Question 13

What is the major product for the following reaction?

Accepted Answer

A)    
B)    
C)    
D)    
E) More than one of these choices. 
A)    
B)    
C)    
D)    
E) More than one of these choices.

Question 14

Name the following compound:

Accepted Answer

A) (R,Z)-5-phenyloct-5-en-3-ol 
B) (R,Z)-5-benzyloct-5-en-3-ol 
C) (R,
E) -5-phenyloct-5-en-3-ol 
D) (R,
E) -5-benzyloct-5-en-3-ol 
E) (R,
E) -5-benzyloct-3-en-6-ol 
A) (R,Z)-5-phenyloct-5-en-3-ol 
B) (R,Z)-5-benzyloct-5-en-3-ol 
C) (R,
E) -5-phenyloct-5-en-3-ol 
D) (R,
E) -5-benzyloct-5-en-3-ol 
E) (R,
E) -5-benzyloct-3-en-6-ol

Question 15

Which statement(s)is/are true of acid-catalyzed alcohol dehydrations?

Accepted Answer

A) Protonation of the alcohol is a fast step. 
B) Formation of a carbocation from the protonated alcohol is a slow step. 
C) Rearrangements of less stable carbocations to more stable carbocations are common. 
D) Loss of a proton by the carbocation intermediate is a fast step. 
E) All of these choices. 
A) Protonation of the alcohol is a fast step. 
B) Formation of a carbocation from the protonated alcohol is a slow step. 
C) Rearrangements of less stable carbocations to more stable carbocations are common. 
D) Loss of a proton by the carbocation intermediate is a fast step. 
E) All of these choices.

Question 16

Which is not a satisfactory procedure for the synthesis of 3-methyl-1-butene?

Accepted Answer

A) (CH3)2CHCCHOHCH3 + conc.H2SO4 
B) (CH3)2CHC$\equiv$ CH + Li/liq.NH3 
C) (CH3)2CHCH2CH2Br + CH3ONa/CH3OH 
D) (CH3)2CHCHBrCH3 + (CH3)3COK/(CH3)3COH 
E) (CH3)2CHC$\equiv$CH + H2/Ni2B (P-2) 
A) (CH3)2CHCCHOHCH3 + conc.H2SO4 
B) (CH3)2CHC$\equiv$ CH + Li/liq.NH3 
C) (CH3)2CHCH2CH2Br + CH3ONa/CH3OH 
D) (CH3)2CHCHBrCH3 + (CH3)3COK/(CH3)3COH 
E) (CH3)2CHC$\equiv$CH + H2/Ni2B (P-2)

Question 17

The main reason why anti-periplaner conformation is preferred in E2 reactions is because the conformation of the hydrogen that is anti to the leaving group provides for a staggered transition state,which is lower in free energy.

Accepted Answer

A) True 
 B)False

Question 18

Which of the following reactions proceeds with inversion of configuration at the carbon bearing the leaving group?

Accepted Answer

A) SN2 
B) SN1 
C) E2 
D) E1 
E) All of these answer choices are correct. 
A) SN2 
B) SN1 
C) E2 
D) E1 
E) All of these answer choices are correct.

Question 19

The ambiguous name dimethylcyclopentene does not clearly distinguish between several structures.
a)Draw the structures of all constitutional isomers corresponding to this name.
b)Indicate which of these is likely to be the most stable,i.e,have the smallest heat of combustion,justifying your rationale briefly.
c)Which of these structures represents an achiral molecule?

Accepted Answer

a) @#IMG-DLM& 
b)Structure I is likely t

Question 20

Which structure represents (R,Z)-5-methylhept-2-ene?

Accepted Answer

A)    
B)    
C)    
D)    
E) None of these choices. 
A)    
B)    
C)    
D)    
E) None of these choices.

Exam 7: Alkenes and Alkynes I

Which alkene would you expect to be the major product of the following dehydration?

Dehydrohalogenation of tert-pentyl bromide at higher temperatures will produce 2-methyl-1-butene as the chief product when:

Which reaction conditions would not yield 2-butyne from 1-propyne?

What would be the major product(s)of the following reaction?

Carbocations are frequent intermediates in acidic reactions of alkenes,alcohols,etc.What do carbocations usually do? They may:

What is the major product for the following reaction sequence?

By analyzing the starting material and the product(s),the following reaction is an example of what type of mechanism?

What is the major product for the following reaction sequence?

Predict the product(s)for the following reaction sequence.

Catalytic hydrogenation utilizing palladium,platinum or nickel proceeds through a process known as ___ catalysis as the metal catalyst is not soluble in the reaction mixture.

The product(s)for the following reaction would mainly be dictated by which mechanism?

What is the major product of the reaction of the following reaction?

What is the major product for the following reaction?

Name the following compound:

Which statement(s)is/are true of acid-catalyzed alcohol dehydrations?

Which is not a satisfactory procedure for the synthesis of 3-methyl-1-butene?

The main reason why anti-periplaner conformation is preferred in E2 reactions is because the conformation of the hydrogen that is anti to the leaving group provides for a staggered transition state,which is lower in free energy.

Which of the following reactions proceeds with inversion of configuration at the carbon bearing the leaving group?

Which structure represents (R,Z)-5-methylhept-2-ene?

The Basics

Families of Carbon

Acids and Bases

Nomenclature and Conformations of Alkanes and Cycloalkanes

Stereochemistry

Nucleophilic Reactions

Alkenes and Alkynes II

Nuclear Magnetic Resonance and Mass Spectrometry

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Reactions at the Α Carbon of Carbonyl Compounds

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

Amines

Transition Metal Complexes

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

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