Question 1

Which of the following solvents could be described as polar and protic?

Accepted Answer

A)  ethanol 
B)  acetonitrile 
C)  dimethylformamide 
D)  acetone 
E)  18-crown-6 
A)  ethanol 
B)  acetonitrile 
C)  dimethylformamide 
D)  acetone 
E)  18-crown-6

Question 2

Circle the aprotic solvents.

Accepted Answer

The answer of Circle the aprotic solvents.  ...

Question 3

Provide the major organic product of the reaction below.

Accepted Answer

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

Question 4

Provide the structure of isopropyl iodide.

Accepted Answer

The answer of Provide the structure of isopropyl iodide....

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

Provide an acceptable name for the compound shown below.

Accepted Answer

4-bromo-1,

Question 7

Arrange the following substrates in order of their increasing SN2 reactivity with NaCN:
bromoethane, 1-chloro-3,3-dimethylpentane, 1-chloro-2,2-dimethylpentane, and 2-bromo-2-methylpentane.

Accepted Answer

2-bromo-2-methylpent

Question 8

Which halide is a better nucleophile, iodide or fluoride? Explain.

Accepted Answer

The iodide ion is the better n

Question 9

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 10

Rank the following molecules in order of increasing relative rate of SN1 solvolysis with methanol and heat (slowest to fastest reacting).

Accepted Answer

A)  3 < 2 < 4 < 5 < 1 
B)  2 < 3 < 4 < 1 < 5 
C)  5 < 4 < 3 < 2 < 1 
D)  2 < 3 < 4 < 5 < 1 
E)  1 < 2 < 5 < 4 < 3 
A)  3 < 2 < 4 < 5 < 1 
B)  2 < 3 < 4 < 1 < 5 
C)  5 < 4 < 3 < 2 < 1 
D)  2 < 3 < 4 < 5 < 1 
E)  1 < 2 < 5 < 4 < 3

Question 11

Predict the two most likely mechanisms that occur when iodocyclohexane is heated in methanol.

Accepted Answer

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

Question 12

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 13

Provide the major organic product of the reaction below.

Accepted Answer

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

Question 14

Provide the major organic product of the reaction below.

Accepted Answer

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

Question 15

Provide the major organic product of the reaction below.

Accepted Answer

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

Question 16

Draw two reasonable resonance structures and the hybrid of the intermediate formed in the following reaction.

Accepted Answer

Free Radic

Question 17

Rank the following compounds in order of increasing reactivity in an SN2 reaction. (Fastest is first, slowest is last.)

Accepted Answer

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

Exam 6: Alkyl Halides; Nucleophilic Substitution

Which of the following solvents could be described as polar and protic?

Circle the aprotic solvents.

Provide the major organic product of the reaction below.

Provide the structure of isopropyl iodide.

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.

Provide an acceptable name for the compound shown below.

Arrange the following substrates in order of their increasing SN2 reactivity with NaCN: bromoethane, 1-chloro-3,3-dimethylpentane, 1-chloro-2,2-dimethylpentane, and 2-bromo-2-methylpentane.

Which halide is a better nucleophile, iodide or fluoride? Explain.

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

Rank the following molecules in order of increasing relative rate of SN1 solvolysis with methanol and heat (slowest to fastest reacting).

Predict the two most likely mechanisms that occur when iodocyclohexane is heated in methanol.

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

Provide the major organic product of the reaction below.

Provide the major organic product of the reaction below.

Provide the major organic product of the reaction below.

Draw two reasonable resonance structures and the hybrid of the intermediate formed in the following reaction.

Rank the following compounds in order of increasing reactivity in an SN2 reaction. (Fastest is first, slowest is last.)

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

Arrange the following substrates in order of their increasing S_N2 reactivity with NaCN: bromoethane, 1-chloro-3,3-dimethylpentane, 1-chloro-2,2-dimethylpentane, and 2-bromo-2-methylpentane.

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

Rank the following molecules in order of increasing relative rate of S_N1 solvolysis with methanol and heat (slowest to fastest reacting).

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

Rank the following compounds in order of increasing reactivity in an S_N2 reaction. (Fastest is first, slowest is last.)