Question 1

The term CFC is an abbreviation for ________.

Accepted Answer

The answer of The term CFC is an abbreviation for...

Question 2

Provide a series of synthetic steps by which (CH3)2C-CH2 could be prepared from 2-methylpropane.

Accepted Answer

1. Br₂, hν

Question 3

Which of the following alkyl chlorides is least likely to undergo rearrangement during a solvolysis reaction?

Accepted Answer

A)  2-chloro-4-methylpentane 
B)  2-chloro-3-methylpentane 
C)  2-chloro-2-methylpentane 
D)  cis-1-chloro-2-ethylcyclohexane 
E)  trans-1-chloro-2-ethylcyclohexane 
A)  2-chloro-4-methylpentane 
B)  2-chloro-3-methylpentane 
C)  2-chloro-2-methylpentane 
D)  cis-1-chloro-2-ethylcyclohexane 
E)  trans-1-chloro-2-ethylcyclohexane

Question 4

SN2 reactions take place with ________ of stereochemistry at the center undergoing substitution.

Accepted Answer

Question 5

Which of the following is a geminal dihalide?

Accepted Answer

A)  cis-1,2-dibromocyclopentane 
B)  3,3-dichloropentane 
C)  trans-1,4-diiodocyclohexane 
D)  isobutyl chloride 
E)  1,3-dibromoheptane 
A)  cis-1,2-dibromocyclopentane 
B)  3,3-dichloropentane 
C)  trans-1,4-diiodocyclohexane 
D)  isobutyl chloride 
E)  1,3-dibromoheptane

Question 6

Which of the following statements describe a favorable attribute of a leaving group? (More than one answer is possible.)

Accepted Answer

A)  The leaving group should be highly polarizable. 
B)  The lower the electronegativity of the leaving group the better. 
C)  Good leaving groups need to have low steric hindrance. 
D)  The departed leaving group should have low basicity. 
A)  The leaving group should be highly polarizable. 
B)  The lower the electronegativity of the leaving group the better. 
C)  Good leaving groups need to have low steric hindrance. 
D)  The departed leaving group should have low basicity.

Question 7

Provide the structure of the major organic product which results in the following reaction.

Accepted Answer

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

Question 8

Provide the structure of the major organic product which results in the following reaction.

Accepted Answer

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

Question 9

Provide the structure of the major organic product which results when 2-bromo-2-methylbutane is treated with sodium ethoxide.

Accepted Answer

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

Question 10

What type of intermediate is present in the SN2 reaction of cyanide with bromoethane?

Accepted Answer

A)  carbocation 
B)  free radical 
C)  carbene 
D)  carbanion 
E)  This reaction has no intermediate. 
A)  carbocation 
B)  free radical 
C)  carbene 
D)  carbanion 
E)  This reaction has no intermediate.

Question 11

Provide the structure of 1-bromo-3-methylhexane.

Accepted Answer

The answer of Provide the structure of 1-bromo-3-methylhexane....

Question 12

Which of the following alkyl halides has the smallest molecular dipole moment?

Accepted Answer

A)  CH3F 
B)  CH3Cl 
C)  CH2I2 
D)  CH2Cl2 
E)  CF4 
A)  CH3F 
B)  CH3Cl 
C)  CH2I2 
D)  CH2Cl2 
E)  CF4

Question 13

Although F is more electronegative than Cl, the C-Cl bond has a larger dipole moment than the C-F bond. Explain.

Accepted Answer

The bond dipole moment is determined by

Question 14

List the following bromides in order of their increasing reactivity as substrates in SN2 reactions: PhBr, PhCH2Br, and PhCH(CH3)Br.

Accepted Answer

PhBr < PhC

Question 15

SN1 reactions usually proceed with:

Accepted Answer

A)  equal amounts of inversion and retention at the center undergoing substitution. 
B)  slightly more inversion than retention at the center undergoing substitution. 
C)  slightly more retention then inversion at the center undergoing substitution. 
D)  complete inversion at the center undergoing substitution. 
E)  complete retention at the center undergoing substitution. 
A)  equal amounts of inversion and retention at the center undergoing substitution. 
B)  slightly more inversion than retention at the center undergoing substitution. 
C)  slightly more retention then inversion at the center undergoing substitution. 
D)  complete inversion at the center undergoing substitution. 
E)  complete retention at the center undergoing substitution.

Question 16

Do all primary iodides react with N3- at the same rate via the SN2 mechanism? Explain.

Accepted Answer

No, not all primary alkyl react with N₃^- a

Question 17

Provide the structure of the major organic product which results in the following reaction.

Accepted Answer

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

Question 18

When trans-1-iodo-4-methylcyclohexane is heated in methanol, the product mixture is primarily ________.

Accepted Answer

A)  a single, chiral compound 
B)  a mixture of diasteromeric ethers 
C)  a mixture of diasteromeric alcohols 
D)  a single, chiral alcohol 
E)  a single, chiral ether 
A)  a single, chiral compound 
B)  a mixture of diasteromeric ethers 
C)  a mixture of diasteromeric alcohols 
D)  a single, chiral alcohol 
E)  a single, chiral ether

Question 19

Which of the following species is the least nucleophilic?

Accepted Answer

A)  H2O 
B)  BF3 
C)  (CH3)3N 
D)  CH3O- 
E)  CN- 
A)  H2O 
B)  BF3 
C)  (CH3)3N 
D)  CH3O- 
E)  CN-

Question 20

The major product from the reaction of 2-chloro-2-methylpentane with sodium ethoxide in ethanol results from which of the following mechanistic pathways?

Accepted Answer

A)  SN1 
B)  SN2 
C)  E1 
D)  E2 
E)  E1cb 
A)  SN1 
B)  SN2 
C)  E1 
D)  E2 
E)  E1cb

Exam 6: Alkyl Halides: Nucleophilic Substitution and Elimination

The term CFC is an abbreviation for ________.

Provide a series of synthetic steps by which (CH3)2C-CH2 could be prepared from 2-methylpropane.

Which of the following alkyl chlorides is least likely to undergo rearrangement during a solvolysis reaction?

SN2 reactions take place with ________ of stereochemistry at the center undergoing substitution.

Which of the following is a geminal dihalide?

Which of the following statements describe a favorable attribute of a leaving group? (More than one answer is possible.)

Provide the structure of the major organic product which results in the following reaction.

Provide the structure of the major organic product which results in the following reaction.

Provide the structure of the major organic product which results when 2-bromo-2-methylbutane is treated with sodium ethoxide.

What type of intermediate is present in the SN2 reaction of cyanide with bromoethane?

Provide the structure of 1-bromo-3-methylhexane.

Which of the following alkyl halides has the smallest molecular dipole moment?

Although F is more electronegative than Cl, the C-Cl bond has a larger dipole moment than the C-F bond. Explain.

List the following bromides in order of their increasing reactivity as substrates in SN2 reactions: PhBr, PhCH2Br, and PhCH(CH3)Br.

SN1 reactions usually proceed with:

Do all primary iodides react with N3- at the same rate via the SN2 mechanism? Explain.

Provide the structure of the major organic product which results in the following reaction.

When trans-1-iodo-4-methylcyclohexane is heated in methanol, the product mixture is primarily ________.

Which of the following species is the least nucleophilic?

The major product from the reaction of 2-chloro-2-methylpentane with sodium ethoxide in ethanol results from which of the following mechanistic pathways?

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

Provide a series of synthetic steps by which (CH₃)₂C-CH₂ could be prepared from 2-methylpropane.

S_N2 reactions take place with ________ of stereochemistry at the center undergoing substitution.

What type of intermediate is present in the S_N2 reaction of cyanide with bromoethane?

List the following bromides in order of their increasing reactivity as substrates in S_N2 reactions: PhBr, PhCH₂Br, and PhCH(CH₃)Br.

S_N1 reactions usually proceed with:

Do all primary iodides react with N₃^- at the same rate via the S_N2 mechanism? Explain.