Question 1

Which of the following compounds will undergo an SN2 reaction most readily?

Accepted Answer

A)  (CH3)3CCH2I 
B)  (CH3)3CCl 
C)  (CH3)2CHI 
D)  (CH3)2CHCH2CH2CH2I 
E)  (CH3)2CHCH2CH2CH2Cl 
A)  (CH3)3CCH2I 
B)  (CH3)3CCl 
C)  (CH3)2CHI 
D)  (CH3)2CHCH2CH2CH2I 
E)  (CH3)2CHCH2CH2CH2Cl

Question 2

Predict the two most likely mechanisms for the reaction of 2-iodohexane with sodium ethoxide.

Accepted Answer

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

Question 3

Provide the structure of the major alkene product of the reaction below.

Accepted Answer

The answer of Provide the structure of the major alkene...

Question 4

List the following bromides in order of their increasing reactivity as substrates in SN1 reactions: 1-iodo-1-ethylcyclopentane, chlorocyclopentane, and iodocyclopentane.

Accepted Answer

chlorocyclopentane <

Question 5

If the absolute configuration at an asymmetric carbon does not change during the course of a reaction, the reaction is said to occur with ________ of stereochemistry.

Accepted Answer

The answer of If the absolute configuration at an asymmetric...

Question 6

When water is shaken with dichloromethane, a two-phase system results. Which compound forms the upper phase? Explain.

Accepted Answer

Water is less dense

Question 7

When 1-bromo-2, 2-dimethylcyclopentane is heated in ethanol, one of the products which results is shown below. Provide a detailed, stepwise mechanism for the production of this compound, and give the name of the mechanism by which it is produced.

Accepted Answer

The answer of When 1-bromo-2, 2-dimethylcyclopentane is heated in ethanol,...

Question 8

Which of the following best describes the carbon-chlorine bond of an alkyl chloride?

Accepted Answer

A)  nonpolar; no dipole 
B)  polar; d+ at carbon and d- at chlorine 
C)  polar; d- at carbon and d+ at chlorine 
D)  ionic 
E)  none of the above 
A)  nonpolar; no dipole 
B)  polar; d+ at carbon and d- at chlorine 
C)  polar; d- at carbon and d+ at chlorine 
D)  ionic 
E)  none of the above

Question 9

Provide the major organic product of the reaction below and a detailed, stepwise mechanism which accounts for its formation.

Accepted Answer

The answer of Provide the major organic product of the...

Question 10

Provide a structure for the major substitution and elimination product of the following reaction.

Accepted Answer

The answer of Provide a structure for the major substitution...

Question 11

Arrange the following alkyl halides in order of increasing boiling point:
CH3CH2Br, CH3CH2CH2Br, (CH3)2CHBr, CH3CH2F.

Accepted Answer

CH₃CH₂F < CH

Question 12

When t-butyl chloride undergoes solvolysis in a solvent mixture composed of 70% water/30% acetone, the reaction rate is slower than when the same compound is solvolyzed in 80% water/20% acetone. Explain.

Accepted Answer

This is purely a solvent effect. The gre

Question 13

Provide the major organic product of the reaction below.

Accepted Answer

The answer of Provide the major organic product of the...

Question 14

List the following compounds in order of increasing reactivity in an SN1 reaction.
CH3Br, CH3CH2CH2I, (CH3)3CI, CH3CHBrCH3, CH3CHICH3

Accepted Answer

CH₃Br < CH₃C

Question 15

Provide an acceptable name for CHCl3.

Accepted Answer

chloroform

Question 16

Provide the name of the bromoalkane shown below.

Accepted Answer

3-bromo-4-

Question 17

Provide a step-by-step mechanism for the reaction below. Include all intermediates, formal charges and correct arrow pushing of electrons.

Accepted Answer

The answer of Provide a step-by-step mechanism for the reaction...

Question 18

Why does CH2=CHCHBrCH3 undergo solvolysis much more rapidly than 2-bromobutane?

Accepted Answer

The intermediate car

Question 19

Provide the major organic product of the reaction below.

Accepted Answer

The answer of Provide the major organic product of the...

Question 20

Which of the following statements correctly describe(s) E1 reactions of alkyl halides (RX)? 
I. Rate = k[base]
II. Rate = k[base][RX]
III. Rate = k[RX]
IV. The reactions occur in two or more distinct steps.
V. Rearrangements are sometimes seen.

Accepted Answer

A)  II and IV 
B)  III and V 
C)  I, IV, and V 
D)  I only 
E)  III, IV, and V 
A)  II and IV 
B)  III and V 
C)  I, IV, and V 
D)  I only 
E)  III, IV, and V

Exam 6: Alkyl Halides: Nucleophilic Substitution and Elimination

Which of the following compounds will undergo an SN2 reaction most readily?

Predict the two most likely mechanisms for the reaction of 2-iodohexane with sodium ethoxide.

Provide the structure of the major alkene product of the reaction below.

List the following bromides in order of their increasing reactivity as substrates in SN1 reactions: 1-iodo-1-ethylcyclopentane, chlorocyclopentane, and iodocyclopentane.

If the absolute configuration at an asymmetric carbon does not change during the course of a reaction, the reaction is said to occur with ________ of stereochemistry.

When water is shaken with dichloromethane, a two-phase system results. Which compound forms the upper phase? Explain.

When 1-bromo-2, 2-dimethylcyclopentane is heated in ethanol, one of the products which results is shown below. Provide a detailed, stepwise mechanism for the production of this compound, and give the name of the mechanism by which it is produced.

Which of the following best describes the carbon-chlorine bond of an alkyl chloride?

Provide the major organic product of the reaction below and a detailed, stepwise mechanism which accounts for its formation.

Provide a structure for the major substitution and elimination product of the following reaction.

Arrange the following alkyl halides in order of increasing boiling point: CH3CH2Br, CH3CH2CH2Br, (CH3)2CHBr, CH3CH2F.

When t-butyl chloride undergoes solvolysis in a solvent mixture composed of 70% water/30% acetone, the reaction rate is slower than when the same compound is solvolyzed in 80% water/20% acetone. Explain.

Provide the major organic product of the reaction below.

List the following compounds in order of increasing reactivity in an SN1 reaction. CH3Br, CH3CH2CH2I, (CH3)3CI, CH3CHBrCH3, CH3CHICH3

Provide an acceptable name for CHCl3.

Provide the name of the bromoalkane shown below.

Provide a step-by-step mechanism for the reaction below. Include all intermediates, formal charges and correct arrow pushing of electrons.

Why does CH2=CHCHBrCH3 undergo solvolysis much more rapidly than 2-bromobutane?

Provide the major organic product of the reaction below.

Which of the following statements correctly describe(s) E1 reactions of alkyl halides (RX)? I. Rate = k[base] II. Rate = k[base][RX] III. Rate = k[RX] IV. The reactions occur in two or more distinct steps. V. Rearrangements are sometimes seen.

Introduction and Review

Structure and Properties of Organic Molecules

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Structure and Synthesis of Alkenes

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

Which of the following compounds will undergo an S_N2 reaction most readily?

List the following bromides in order of their increasing reactivity as substrates in S_N1 reactions: 1-iodo-1-ethylcyclopentane, chlorocyclopentane, and iodocyclopentane.

Arrange the following alkyl halides in order of increasing boiling point: CH₃CH₂Br, CH₃CH₂CH₂Br, (CH₃)₂CHBr, CH₃CH₂F.

List the following compounds in order of increasing reactivity in an S_N1 reaction. CH₃Br, CH₃CH₂CH₂I, (CH₃)₃CI, CH₃CHBrCH₃, CH₃CHICH₃

Provide an acceptable name for CHCl₃.

Why does CH₂=CHCHBrCH₃ undergo solvolysis much more rapidly than 2-bromobutane?