Question 1

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 2

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 3

Which of the following factors is favorable for nucleophilicity but not basicity?

Accepted Answer

A)  highly polarizable 
B)  low electronegativity 
C)  negatively charged 
D)  sterically hindered 
A)  highly polarizable 
B)  low electronegativity 
C)  negatively charged 
D)  sterically hindered

Question 4

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

Accepted Answer

The iodide ion is the better n

Question 5

Provide $\underline{\text{ two }}$  circumstances under which solvolysis of a chiral alkyl halide would not result in the generation of a mixture of enantiomeric products.

Accepted Answer

Choose two from among:
(i) leaving group

Question 6

When (cis)-1-bromo-2 methylcyclohexane is treated with methanol and heat, four different products are formed - two by substitution and two by elimination.   Which of the following conditions would change the outcome of this reaction by promoting the production of 3-methylhexene as the major product?

Accepted Answer

A)  KOH, ethanol and heat 
B)  water/acetone and heat 
C)  tert-butoxide/tert-butyl alcohol 
D)  tert-butyl alcohol and heat 
E)  methoxide/methanol 
A)  KOH, ethanol and heat 
B)  water/acetone and heat 
C)  tert-butoxide/tert-butyl alcohol 
D)  tert-butyl alcohol and heat 
E)  methoxide/methanol

Question 7

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 8

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 9

A sample of 1-chloro-1-phenylethane with an [α]25D of -94.8∘ is reacted with NH3 in methanol/water solvent. The major substitution product of the reaction is 1-phenyl-1-ethylamine with an [α]25D of -8.6∘. Given that optically pure (R) 1-chloro-1-phenylethane has a specific rotation of -109.0∘ and that optically pure (R) 1-phenyl-1-ethylamine has a specific rotation of +39.3∘, which of the following statements best describes this reaction?

Accepted Answer

A)  Net inversion 25% with 75% racemization -- SN1 mechanism 
B)  Net inversion 12% with 88% racemization -- SN1 mechanism 
C)  Net inversion 75% with 25% racemization -- SN2 mechanism 
D)  Net inversion 12% with 88% racemization -- SN2 mechanism 
E)  Net inversion 88% with 12% racemization -- SN2 mechanism 
A)  Net inversion 25% with 75% racemization -- SN1 mechanism 
B)  Net inversion 12% with 88% racemization -- SN1 mechanism 
C)  Net inversion 75% with 25% racemization -- SN2 mechanism 
D)  Net inversion 12% with 88% racemization -- SN2 mechanism 
E)  Net inversion 88% with 12% racemization -- SN2 mechanism

Question 10

Name one factor that is favorable for nucleophilicity but not for basicity.

Accepted Answer

The answer of Name one factor that is favorable for...

Question 11

How many distinct alkene products are possible when the alkyl iodide below undergoes E2 elimination?

Accepted Answer

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

Question 12

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 13

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 14

When 3-iodo-3-ethylpentane is heated 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)  alcohol, E1 
A)  ether, SN1 
B)  ether, SN2 
C)  ether, E1 
D)  alkene, E2 
E)  alcohol, E1

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

Provide the major organic product of the reaction below.

Accepted Answer

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

Question 17

Which of the following compounds is the most nucleophilic?

Accepted Answer

A)  CH3SH 
B)  CH3OH 
C)  H2O 
D)  CH3CO2H 
E)  BF3 
A)  CH3SH 
B)  CH3OH 
C)  H2O 
D)  CH3CO2H 
E)  BF3

Question 18

When 1-iodo-1-methylcyclohexane is treated with NaOCH2CH3 the more highly substituted alkene product predominates. When KOC(CH3)3 is used instead, the less highly substituted alkene product predominates. Offer an explanation.

Accepted Answer

The unhindered ethoxide procedures the m

Question 19

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 20

Provide the major organic product of the reaction below.

Accepted Answer

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

Exam 6: Alkyl Halides: Nucleophilic Substitution and Elimination

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

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

Which of the following factors is favorable for nucleophilicity but not basicity?

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

Provide two ‾\underline{\text{ two }} two ​ circumstances under which solvolysis of a chiral alkyl halide would not result in the generation of a mixture of enantiomeric products.

When (cis)-1-bromo-2 methylcyclohexane is treated with methanol and heat, four different products are formed - two by substitution and two by elimination. Which of the following conditions would change the outcome of this reaction by promoting the production of 3-methylhexene as the major product?

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

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

Name one factor that is favorable for nucleophilicity but not for basicity.

How many distinct alkene products are possible when the alkyl iodide below undergoes E2 elimination?

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

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

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

Provide the major organic product of the reaction below.

Provide the major organic product of the reaction below.

Which of the following compounds is the most nucleophilic?

When 1-iodo-1-methylcyclohexane is treated with NaOCH2CH3 the more highly substituted alkene product predominates. When KOC(CH3)3 is used instead, the less highly substituted alkene product predominates. Offer an explanation.

Which of the following is a secondary alkyl halide?

Provide the major organic product of the reaction below.

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 mechanisms (S_N1, S_N2, E1, E2) feature(s) a carbocation intermediate?

Provide $\underline{\text{ two }}$ circumstances under which solvolysis of a chiral alkyl halide would not result in the generation of a mixture of enantiomeric products.

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

When 3-iodo-3-ethylpentane is heated in methanol, the major organic product is an that is generated through an mechanism.

When 1-iodo-1-methylcyclohexane is treated with NaOCH₂CH₃ the more highly substituted alkene product predominates. When KOC(CH₃)₃ is used instead, the less highly substituted alkene product predominates. Offer an explanation.