Question 1

What is the most likely mechanism for the reaction below?

Accepted Answer

A)  SN1 
B)  SN2 
C)  E1 
D)  E2 
A)  SN1 
B)  SN2 
C)  E1 
D)  E2 D

Question 2

What is (are) the product(s) of the following reaction?

Accepted Answer

A)  I and II 
B)  II and III 
C)  I and III 
D)  I, II and III 
A)  I and II 
B)  II and III 
C)  I and III 
D)  I, II and III D

Question 3

Which of the following alkyl halides would afford the indicated product upon reaction with sodium methoxide?

Accepted Answer

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

Question 4

Classify each alkene in vitamin D3 labeled I, II, III by the number of carbon substituents bonded to the double bond.

Accepted Answer

A)  I = Disubstituted; II = trisubstituted; III = trisubstituted. 
B)  I = Monosubstituted; II = disubstituted; III = trisubstituted. 
C)  I = Disubstituted; II = disubstituted; III = trisubstituted. 
D)  I = Disubstituted; II = trisubstituted; III = disubstituted. 
A)  I = Disubstituted; II = trisubstituted; III = trisubstituted. 
B)  I = Monosubstituted; II = disubstituted; III = trisubstituted. 
C)  I = Disubstituted; II = disubstituted; III = trisubstituted. 
D)  I = Disubstituted; II = trisubstituted; III = disubstituted.

Question 5

Which of the following alkenes is the most stable?

Accepted Answer

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

Question 6

How many unique F1F1F1S1F1F1F10 carbons are found in the alkyl halide below?

Accepted Answer

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

Question 7

What is (are) the elimination product(s) of the following reaction?

Accepted Answer

A)  Only I 
B)  Only II 
C)  Only III 
D)  II and III 
A)  Only I 
B)  Only II 
C)  Only III 
D)  II and III

Question 8

Which alkyl halide(s) would give the following alkene as the only product in an elimination reaction?

Accepted Answer

A)  Only I 
B)  Only II 
C)  Only III 
D)  I and II 
A)  Only I 
B)  Only II 
C)  Only III 
D)  I and II

Question 9

Which of the following statements about the mechanism of an E2 reaction is not true?

Accepted Answer

A)  It is fastest with tertiary halides. 
B)  It exhibits first-order kinetics. 
C)  A better leaving group should make a faster reaction. 
D)  All bonds are broken and formed in a single step. 
A)  It is fastest with tertiary halides. 
B)  It exhibits first-order kinetics. 
C)  A better leaving group should make a faster reaction. 
D)  All bonds are broken and formed in a single step.

Question 10

What is the major elimination product obtained from the following reaction?

Accepted Answer

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

Question 11

What is (are) the product(s) of the following reaction?

Accepted Answer

A)  Only I 
B)  Only II 
C)  Only III 
D)  I and II 
A)  Only I 
B)  Only II 
C)  Only III 
D)  I and II

Question 12

What is the major product of the following reaction?

Accepted Answer

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

Question 13

How many unique F1F1F1S1F1F1F10 carbons are found in the alkyl halide below?

Accepted Answer

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

Question 14

Which of the following alkyl halides will afford the product below as the major product in an E2 reaction?

Accepted Answer

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

Question 15

What is (are) the starting material(s) in the reaction below?

Accepted Answer

A)  Only I 
B)  Only II 
C)  Only III 
D)  II and III 
A)  Only I 
B)  Only II 
C)  Only III 
D)  II and III

Question 16

What is the most likely mechanism for the reaction below?

Accepted Answer

A)  SN1 
B)  SN2 
C)  E1 
D)  E2 
A)  SN1 
B)  SN2 
C)  E1 
D)  E2

Question 17

Which of the following statements about an E1 mechanism is true?

Accepted Answer

A)  The identity of the leaving group affects the rate of reaction. 
B)  The reaction follows second-order kinetics. 
C)  The reaction is slowest with tertiary substrates. 
D)  Polar aprotic solvents favor the E1 mechanism. 
A)  The identity of the leaving group affects the rate of reaction. 
B)  The reaction follows second-order kinetics. 
C)  The reaction is slowest with tertiary substrates. 
D)  Polar aprotic solvents favor the E1 mechanism.

Question 18

Which of the following is the major E2 product formed from the following alkyl halide?

Accepted Answer

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

Question 19

Which of the following is the most reactive substrate in an E2 reaction? $\mathrm { CH } _ { 3 } \mathrm { Br } \quad \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { Br } \quad \mathrm { CH } _ { 3 } \mathrm { CH } \left( \mathrm { Br } ^ { 2 } \right) \mathrm { CH } _ { 2 } \mathrm { CH } _ { 3 } \quad \left( \mathrm { CH } _ { 3 } \right) _ { 3 } \mathrm { CBr }$
I $\quad\quad\quad\quad\quad\quad\quad$II$\quad\quad\quad\quad\quad\quad\quad\quad\quad\quad$III$\quad\quad\quad\quad\quad\quad\quad\quad$IV

Accepted Answer

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

Question 20

What is the product of the following reaction?

Accepted Answer

A)  Only I 
B)  Only II 
C)  Only III 
D)  II and III 
A)  Only I 
B)  Only II 
C)  Only III 
D)  II and III

Exam 8: Alkyl Halides and Elimination Reactions

What is the most likely mechanism for the reaction below?

What is (are) the product(s) of the following reaction?

Which of the following alkyl halides would afford the indicated product upon reaction with sodium methoxide?

Classify each alkene in vitamin D3 labeled I, II, III by the number of carbon substituents bonded to the double bond.

Which of the following alkenes is the most stable?

How many unique  carbons are found in the alkyl halide below?

What is (are) the elimination product(s) of the following reaction?

Which alkyl halide(s) would give the following alkene as the only product in an elimination reaction?

Which of the following statements about the mechanism of an E2 reaction is not true?

What is the major elimination product obtained from the following reaction?

What is (are) the product(s) of the following reaction?

What is the major product of the following reaction?

How many unique  carbons are found in the alkyl halide below?

Which of the following alkyl halides will afford the product below as the major product in an E2 reaction?

What is (are) the starting material(s) in the reaction below?

What is the most likely mechanism for the reaction below?

Which of the following statements about an E1 mechanism is true?

Which of the following is the major E2 product formed from the following alkyl halide?

What is the product of the following reaction?

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alcohols, Ethers and Epoxides

Alkenes

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Electrophilic Aromatic Substitution

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones Nucleophilic Addition

Carboxylic Acids and Derivatives

Substitution Reactions of Carbonyl Compounds at the Alpha-Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Lipids

Synthetic Polymers

Filters

Classify each alkene in vitamin D₃ labeled I, II, III by the number of carbon substituents bonded to the double bond.