Question 1

What kind of reactive intermediate is present in the mechanism of the following reaction?

Accepted Answer

A)  alkyne 
B)  allylic anion 
C)  allylic cation 
D)  allylic radical 
E)  benzylic cation 
A)  alkyne 
B)  allylic anion 
C)  allylic cation 
D)  allylic radical 
E)  benzylic cation D

Question 2

Provide the reagents necessary for carrying out the transformation of cyclopentane to cyclopentene.

Accepted Answer

1. Br₂, hν 2. NaOH, acetone

Question 3

By what mechanism does cyclohexanol react when treated in sulfuric acid and what compound results?

Accepted Answer

A)  E1; methoxycyclohexane 
B)  E2; methoxycyclohexane 
C)  SN1; methoxycyclohexane 
D)  E2; cyclohexene 
E)  E1; cyclohexene 
A)  E1; methoxycyclohexane 
B)  E2; methoxycyclohexane 
C)  SN1; methoxycyclohexane 
D)  E2; cyclohexene 
E)  E1; cyclohexene E

Question 4

Provide the proper IUPAC name for the alkene shown below.

Accepted Answer

6-bromo-1-

Question 5

Describe the major elimination products of the following reaction, including any stereochemistry, and indicate which structure will predominate. Explain and defend your answer.

Accepted Answer

Possible products: @#IMG-DLM& This reaction would

Question 6

Name the alkene shown. Be sure to include the appropriate E or Z label necessary.

Accepted Answer

(E)-1-brom

Question 7

Using Zaitsev's rule, choose the most stable alkene among the following.

Accepted Answer

A)  hex-1-ene 
B)  (
E) -hex-2-ene 
C)  (Z)-hex-2-ene 
D)  They are all of equal stability according to Zaitsev's rule. 
A)  hex-1-ene 
B)  (
E) -hex-2-ene 
C)  (Z)-hex-2-ene 
D)  They are all of equal stability according to Zaitsev's rule.

Question 8

Name the alkene shown. Be sure to include the appropriate E or Z label necessary.

Accepted Answer

2,5-dichlo

Question 9

Does the alkene shown below violate Bredt's rule?

Accepted Answer

The answer of Does the alkene shown below violate Bredt's...

Question 10

How many elements of unsaturation are implied by the molecular formula C7H11Cl?

Accepted Answer

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

Question 11

Provide an acceptable name for (CH3CH2)2CHCH2CH=CH2.

Accepted Answer

4-ethyl-1-

Question 12

Draw all likely alkene products in the following reaction and circle the product you expect to predominate.

Accepted Answer

No alkene

Question 13

Which of the following alkenes has the largest molar heat of hydrogenation (ie, releases the most heat upon hydrogenation)?

Accepted Answer

A)  2,3-dimethyl-2-butene 
B)  2-methyl-2-butene 
C)  $\underline{\text{ trans }}$-2-butene 
D)  $\underline{\text{  cis }}$ -2-butene 
E)  1-hexene 
A)  2,3-dimethyl-2-butene 
B)  2-methyl-2-butene 
C)  $\underline{\text{ trans }}$-2-butene 
D)  $\underline{\text{  cis }}$ -2-butene 
E)  1-hexene

Question 14

The steroid testosterone has the molecular formula C19H28O2. Given that there are two P -bond in a molecule of testosterone, how many rings are present in each molecule?

Accepted Answer

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

Question 15

Dehydrohalogenation of 2-bromobutane in the presence of a strong base proceeds via which of the following mechanistic pathways?

Accepted Answer

A)  SN1 
B)  SN2 
C)  E1 
D)  E2 
E)  none of the above 
A)  SN1 
B)  SN2 
C)  E1 
D)  E2 
E)  none of the above

Question 16

Compare the relative heats of hydrogenation of cyclobutene and cyclopentene and explain the difference in magnitude.

Accepted Answer

Cyclobutene's heat of hydrogen

Question 17

Which of the following alkenes is the major product when 2-bromo-2-methylpentane is treated with sodium ethoxide in ethanol?

Accepted Answer

A)  2-methylpent-1-ene 
B)  2-methylpent-2-ene 
C)  (
E) -4-methylpent-2-ene 
D)  (Z)-4-methylpent-2-ene 
E)  4-methylpent-1-ene 
A)  2-methylpent-1-ene 
B)  2-methylpent-2-ene 
C)  (
E) -4-methylpent-2-ene 
D)  (Z)-4-methylpent-2-ene 
E)  4-methylpent-1-ene

Question 18

Propose a detailed, step-by-step mechanism for the reaction pathway shown below.

Accepted Answer

The answer of Propose a detailed, step-by-step mechanism for the...

Question 19

Which of the alkyl chlorides listed below undergoes dehydrohalogenation in the presence of a strong base to give pent-2-ene as the only alkene product?

Accepted Answer

A)  1-chloropentane 
B)  2-chloropentane 
C)  3-chloropentane 
D)  1-chloro-2-methylbutane 
E)  1-chloro-3-methylbutane 
A)  1-chloropentane 
B)  2-chloropentane 
C)  3-chloropentane 
D)  1-chloro-2-methylbutane 
E)  1-chloro-3-methylbutane

Question 20

Provide an acceptable name for (CH3)2CHCH=C(CH3)CH2CH3.

Accepted Answer

2,4-dimeth

Exam 7: Structure and Synthesis of Alkenes

What kind of reactive intermediate is present in the mechanism of the following reaction?

Provide the reagents necessary for carrying out the transformation of cyclopentane to cyclopentene.

By what mechanism does cyclohexanol react when treated in sulfuric acid and what compound results?

Provide the proper IUPAC name for the alkene shown below.

Describe the major elimination products of the following reaction, including any stereochemistry, and indicate which structure will predominate. Explain and defend your answer.

Name the alkene shown. Be sure to include the appropriate E or Z label necessary.

Using Zaitsev's rule, choose the most stable alkene among the following.

Name the alkene shown. Be sure to include the appropriate E or Z label necessary.

Does the alkene shown below violate Bredt's rule?

How many elements of unsaturation are implied by the molecular formula C7H11Cl?

Provide an acceptable name for (CH3CH2)2CHCH2CH=CH2.

Draw all likely alkene products in the following reaction and circle the product you expect to predominate.

Which of the following alkenes has the largest molar heat of hydrogenation (ie, releases the most heat upon hydrogenation)?

The steroid testosterone has the molecular formula C19H28O2. Given that there are two P -bond in a molecule of testosterone, how many rings are present in each molecule?

Dehydrohalogenation of 2-bromobutane in the presence of a strong base proceeds via which of the following mechanistic pathways?

Compare the relative heats of hydrogenation of cyclobutene and cyclopentene and explain the difference in magnitude.

Which of the following alkenes is the major product when 2-bromo-2-methylpentane is treated with sodium ethoxide in ethanol?

Propose a detailed, step-by-step mechanism for the reaction pathway shown below.

Which of the alkyl chlorides listed below undergoes dehydrohalogenation in the presence of a strong base to give pent-2-ene as the only alkene product?

Provide an acceptable name for (CH3)2CHCH=C(CH3)CH2CH3.

Introduction and Review

Structure and Properties of Organic Molecules

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides: Nucleophilic Substitution and Elimination

Reactions of Alkenes

Alkynes

Structure and Synthesis of Alcohols

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Ethers, Epoxides, and Thioethers

Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Aromatic Compounds

Reactions of Aromatic Compounds

Ketones and Aldehydes

Amines

Carboxylic Acids

Carboxylic Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

How many elements of unsaturation are implied by the molecular formula C₇H₁₁Cl?

Provide an acceptable name for (CH₃CH₂)₂CHCH₂CH=CH₂.

The steroid testosterone has the molecular formula C₁₉H₂₈O₂. Given that there are two P -bond in a molecule of testosterone, how many rings are present in each molecule?

Provide an acceptable name for (CH₃)₂CHCH=C(CH₃)CH₂CH₃.