Question 1

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

Accepted Answer

The intermediate car

Question 2

Provide an acceptable name for the compound shown below.

Accepted Answer

cis-1, 2-d

Question 3

Which of the following alkyl halides reacts most rapidly via an SN2 reaction with NaCN?

Accepted Answer

A)  1-iodohexane 
B)  1-fluorohexane 
C)  (R)-2-bromohexane 
D)  iodocyclohexane 
E)  1-iodo-1-methylcyclohexane 
A)  1-iodohexane 
B)  1-fluorohexane 
C)  (R)-2-bromohexane 
D)  iodocyclohexane 
E)  1-iodo-1-methylcyclohexane

Question 4

Arrange the following compounds in order of increasing reactivity toward ethanol solvolysis:
t-butyl bromide, t-butyl iodide, isopropyl chloride, methyl iodide.

Accepted Answer

methyl iodide < isop

Question 5

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 6

When 3-iodo-3-ethylpentane is treated with sodium methoxide in methanol, the major organic product is an ________ that is generated through an ________ mechanism.

Accepted Answer

A)  ether; SN1 
B)  ether; SN2 
C)  ether; E1 
D)  alkene; E2 
E)  alkene; E1 
A)  ether; SN1 
B)  ether; SN2 
C)  ether; E1 
D)  alkene; E2 
E)  alkene; E1

Question 7

Draw the highest energy transition state in the solvolysis of (CH3)3CI in CH3OH.

Accepted Answer

Question 8

Show the best way to prepare CH3OCH(CH3)2 by an SN2 reaction.

Accepted Answer

Question 9

Provide the major organic product of the reaction below.

Accepted Answer

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

Question 10

Which of the following mechanisms (SN1, SN2, E1, E2) feature(s) a carbocation intermediate?

Accepted Answer

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

Question 11

Draw the structures of the two major products formed in the following reaction. Indicate which of the two structures would be predicted to predominate under thermodynamic condition and explain why.

Accepted Answer

Reactivity of allylic hydrogens due to r

Question 12

Which of the cations below would be subject to a structural rearrangement?

Accepted Answer

A)  1 
B)  3 
C)  1, 2, & 3 
D)  2 & 3 
A)  1 
B)  3 
C)  1, 2, & 3 
D)  2 & 3

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

Do all primary alkyl iodides undergo SN2 reactions with sodium cyanide in DMSO at identical rates? Explain.

Accepted Answer

No. All primary iodides are no

Question 15

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 16

Show how the following reaction might be constructed using an SN2 reaction by drawing structures for the starting materials.

Accepted Answer

Question 17

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

Accepted Answer

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

Question 18

When a SN1 reaction of R-2-iodobutane takes place in hot methanol, the product ________.

Accepted Answer

A)  is chiral 
B)  will rotate plane polarized light 
C)  is racemic 
D)  will undergo a hydride shift 
E)  none of the above 
A)  is chiral 
B)  will rotate plane polarized light 
C)  is racemic 
D)  will undergo a hydride shift 
E)  none of the above

Question 19

The following structure is a proteasome inhibitor that may find application in treating cervical cancer (J. Med. Chem. 2011, 449). The halides in this structure may be classified as ________ and ________.

Accepted Answer

A)  vicinal; vinyl 
B)  vicinal; aryl 
C)  vinyl; aryl 
D)  vinyl; geminal 
A)  vicinal; vinyl 
B)  vicinal; aryl 
C)  vinyl; aryl 
D)  vinyl; geminal

Question 20

What is the IUPAC name of the compound shown below?

Accepted Answer

A)  (2R,3S,4S)-2-chloro-3,4-dibromo-3-methylhexane 
B)  (2R,3S,4S)-3,4-dibromo-2-chloro-3-methylhexane 
C)  (3S,4S,5S)-3,4-dibromo-5-chloro-4-methylhexane 
D)  (2R,3R,4S)-3,4-dibromo-2-chloro-3-methylhexane 
E)  (2R,3S,4R)-3,4-dibromo-2-chloro-3-methylhexane 
A)  (2R,3S,4S)-2-chloro-3,4-dibromo-3-methylhexane 
B)  (2R,3S,4S)-3,4-dibromo-2-chloro-3-methylhexane 
C)  (3S,4S,5S)-3,4-dibromo-5-chloro-4-methylhexane 
D)  (2R,3R,4S)-3,4-dibromo-2-chloro-3-methylhexane 
E)  (2R,3S,4R)-3,4-dibromo-2-chloro-3-methylhexane

Exam 6: Alkyl Halides; Nucleophilic Substitution

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

Provide an acceptable name for the compound shown below.

Which of the following alkyl halides reacts most rapidly via an SN2 reaction with NaCN?

Arrange the following compounds in order of increasing reactivity toward ethanol solvolysis: t-butyl bromide, t-butyl iodide, isopropyl chloride, methyl iodide.

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

When 3-iodo-3-ethylpentane is treated with sodium methoxide in methanol, the major organic product is an ________ that is generated through an ________ mechanism.

Draw the highest energy transition state in the solvolysis of (CH3)3CI in CH3OH.

Show the best way to prepare CH3OCH(CH3)2 by an SN2 reaction.

Provide the major organic product of the reaction below.

Which of the following mechanisms (SN1, SN2, E1, E2) feature(s) a carbocation intermediate?

Draw the structures of the two major products formed in the following reaction. Indicate which of the two structures would be predicted to predominate under thermodynamic condition and explain why.

Which of the cations below would be subject to a structural rearrangement?

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

Do all primary alkyl iodides undergo SN2 reactions with sodium cyanide in DMSO at identical rates? Explain.

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

Show how the following reaction might be constructed using an SN2 reaction by drawing structures for the starting materials.

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

When a SN1 reaction of R-2-iodobutane takes place in hot methanol, the product ________.

The following structure is a proteasome inhibitor that may find application in treating cervical cancer (J. Med. Chem. 2011, 449). The halides in this structure may be classified as ________ and ________.

What is the IUPAC name of the compound shown 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

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

Which of the following alkyl halides reacts most rapidly via an S_N2 reaction with NaCN?

When 3-iodo-3-ethylpentane is treated with sodium methoxide in methanol, the major organic product is an that is generated through an mechanism.

Draw the highest energy transition state in the solvolysis of (CH₃)₃CI in CH₃OH.

Show the best way to prepare CH₃OCH(CH₃)₂ by an S_N2 reaction.

Which of the following mechanisms (S_N1, S_N2, E1, E2) feature(s) a carbocation intermediate?

Do all primary alkyl iodides undergo S_N2 reactions with sodium cyanide in DMSO at identical rates? Explain.

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

Show how the following reaction might be constructed using an S_N2 reaction by drawing structures for the starting materials.

When a S_N1 reaction of R-2-iodobutane takes place in hot methanol, the product ________.

The following structure is a proteasome inhibitor that may find application in treating cervical cancer (J. Med. Chem. 2011, 449). The halides in this structure may be classified as and .