Question 1

Provide the structure of the major organic product in the following reaction.
(CH3)3N + CH3CH2CH2I →

Accepted Answer

Question 2

Arrange the following species in order of increasing nucleophilicity:
CH3CH2S-, CH3CH2O-, (CH3)3CO-, (CH3)3COH.

Accepted Answer

(CH₃)₃COH <

Question 3

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 4

Provide an acceptable name for CHCl3.

Accepted Answer

chloroform

Question 5

Provide the structure of the major organic product in the reaction below.

Accepted Answer

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

Question 6

Provide the structure of the major organic product which results when (S)-2-iodopentane is treated with KCN in DMF.

Accepted Answer

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

Question 7

Provide a detailed, stepwise mechanism for the reaction below.
(CH3)2CHCH2CH2CH2I + CN- → (CH3)2CHCH2CH2CH2CH2CN + I-

Accepted Answer

Question 8

What general classification is given to the molecule below?

Accepted Answer

A)  primary chloride 
B)  secondary chloride 
C)  tertiary chloride 
D)  vinyl chloride 
E)  benzyl chloride 
A)  primary chloride 
B)  secondary chloride 
C)  tertiary chloride 
D)  vinyl chloride 
E)  benzyl chloride

Question 9

List the following bromides in order of their increasing reactivity as substrates in SN1 reactions: PhBr, PhCH2Br, and PhCH(CH3)Br.

Accepted Answer

PhBr < PhC

Question 10

Which of the following alkyl halides can produce only a single alkene product from when treated with sodium methoxide?

Accepted Answer

A)  2-chloro-2-methylpentane 
B)  3-chloro-3-ethylpentane 
C)  3-chloro-2-methylpentane 
D)  2-chloro-4-methylpentane 
E)  2-chloro-3-ethylpentane 
A)  2-chloro-2-methylpentane 
B)  3-chloro-3-ethylpentane 
C)  3-chloro-2-methylpentane 
D)  2-chloro-4-methylpentane 
E)  2-chloro-3-ethylpentane

Question 11

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

Accepted Answer

CH₃Br < CH₃C

Question 12

Which of the following is a secondary halide?

Accepted Answer

A)  ClCH2CH2C(CH3)3 
B)  ClCH2CH2CH(CH3)2 
C)  (CH3)2CClCH2CH3 
D)  (CH3)3CCHClCH3 
E)  ClCH2C(CH3)CH2CH3 
A)  ClCH2CH2C(CH3)3 
B)  ClCH2CH2CH(CH3)2 
C)  (CH3)2CClCH2CH3 
D)  (CH3)3CCHClCH3 
E)  ClCH2C(CH3)CH2CH3

Question 13

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 14

Which of the following best describes DDT?

Accepted Answer

A)  a chlorocarbon used to decaffeinate coffee beans 
B)  a polybrominated organic compound used as a herbicide 
C)  a Freon used as a foaming agent 
D)  a mixed alkyl halide used as an anesthetic 
E)  a polychlorinated organic compound used as an insecticide 
A)  a chlorocarbon used to decaffeinate coffee beans 
B)  a polybrominated organic compound used as a herbicide 
C)  a Freon used as a foaming agent 
D)  a mixed alkyl halide used as an anesthetic 
E)  a polychlorinated organic compound used as an insecticide

Question 15

Provide the structure of the major organic products which result in the reaction below.

Accepted Answer

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

Question 16

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 17

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

Question 18

Which of the following is a secondary alkyl halide?

Accepted Answer

A)  methyl bromide 
B)  isopropyl chloride 
C)  t-butyl iodide 
D)  propyl bromide 
E)  isobutyl chloride 
A)  methyl bromide 
B)  isopropyl chloride 
C)  t-butyl iodide 
D)  propyl bromide 
E)  isobutyl chloride

Question 19

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

Accepted Answer

CH₃CH₂F < CH

Question 20

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

Accepted Answer

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

Exam 6: Alkyl Halides; Nucleophilic Substitution

Provide the structure of the major organic product in the following reaction. (CH3)3N + CH3CH2CH2I →

Arrange the following species in order of increasing nucleophilicity: CH3CH2S-, CH3CH2O-, (CH3)3CO-, (CH3)3COH.

Which of the following is a geminal dihalide?

Provide an acceptable name for CHCl3.

Provide the structure of the major organic product in the reaction below.

Provide the structure of the major organic product which results when (S)-2-iodopentane is treated with KCN in DMF.

Provide a detailed, stepwise mechanism for the reaction below. (CH3)2CHCH2CH2CH2I + CN- → (CH3)2CHCH2CH2CH2CH2CN + I-

What general classification is given to the molecule below?

List the following bromides in order of their increasing reactivity as substrates in SN1 reactions: PhBr, PhCH2Br, and PhCH(CH3)Br.

Which of the following alkyl halides can produce only a single alkene product from when treated with sodium methoxide?

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

Which of the following is a secondary halide?

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

Which of the following best describes DDT?

Provide the structure of the major organic products which result in the reaction below.

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

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

Which of the following is a secondary alkyl halide?

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

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

Structure and Bonding

Acids and Bases; Functional Groups

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Structure and Synthesis of Alkenes; Elimination

Reactions of Alkenes

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 the structure of the major organic product in the following reaction. (CH₃)₃N + CH₃CH₂CH₂I →

Arrange the following species in order of increasing nucleophilicity: CH₃CH₂S^-, CH₃CH₂O^-, (CH₃)₃CO^-, (CH₃)₃COH.

Provide an acceptable name for CHCl₃.

Provide a detailed, stepwise mechanism for the reaction below. (CH₃)₂CHCH₂CH₂CH₂I + CN^- → (CH₃)₂CHCH₂CH₂CH₂CH₂CN + I^-

List the following bromides in order of their increasing reactivity as substrates in S_N1 reactions: PhBr, PhCH₂Br, and PhCH(CH₃)Br.

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

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