Question 1

Which of the following mechanistically depicts the protonation of tert-butyl alcohol by hydrogen bromide?

Accepted Answer

A)  
  
B)  
  
C)  
  
D)  
  
A)  
  
B)  
  
C)  
  
D)  
  A

Question 2

Dibromination of isopropylcyclopentane gives a product which can be isolated in good yields. Which of the following would you predict to be this product?

Accepted Answer

A)  A 
B)  B 
C)  C 
D)  D 
A)  A 
B)  B 
C)  C 
D)  D B

Question 3

The central carbon of the tert-butyl carbocation, $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}^{+}$, is

Accepted Answer

A)  $\mathrm{sp}^{2}$ hybridized with $\mathrm{a}+1$ formal charge. 
B)  $\mathrm{sp}^{2}$ hybridized with a 0 formal charge. 
C)  $\mathrm{sp}^{3}$ hybridized with $\mathrm{a}+1$ formal charge. 
D)  $\mathrm{sp}^{3}$ hybridized with a 0 formal charge. 
A)  $\mathrm{sp}^{2}$ hybridized with $\mathrm{a}+1$ formal charge. 
B)  $\mathrm{sp}^{2}$ hybridized with a 0 formal charge. 
C)  $\mathrm{sp}^{3}$ hybridized with $\mathrm{a}+1$ formal charge. 
D)  $\mathrm{sp}^{3}$ hybridized with a 0 formal charge. A

Question 4

What is the IUPAC name of the compound below?

Accepted Answer

A)  8-chloro-4-isopropyl-4,7-dimethylnonane 
B)  2-chloro-6-isopropyl-3,6-dimethylnonane 
C)  2-chloro-3,6,7-trimethyl-6-propyloctane 
D)  6-sec-butyl-2-chloro-3,6-dimethyloctane 
A)  8-chloro-4-isopropyl-4,7-dimethylnonane 
B)  2-chloro-6-isopropyl-3,6-dimethylnonane 
C)  2-chloro-3,6,7-trimethyl-6-propyloctane 
D)  6-sec-butyl-2-chloro-3,6-dimethyloctane

Question 5

If the compound below containing three types of alcohols were exposed to ONLY 1 equivalent of $\mathrm{HCl}$, what major product would you expect?

Accepted Answer

A)    
B)  
  
C)  
  
D)  there is no way to know 
A)    
B)  
  
C)  
  
D)  there is no way to know

Question 6

What are the products of the following reaction?

Accepted Answer

A)  1-bromobutane and water 
B)  1-bromobutane and hydrogen 
C)  butane and $\mathrm{HOBr}$ 
D)  $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OBr}+$ hydrogen 
A)  1-bromobutane and water 
B)  1-bromobutane and hydrogen 
C)  butane and $\mathrm{HOBr}$ 
D)  $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OBr}+$ hydrogen

Question 7

Which one of the following gives a single monochlorination product?

Accepted Answer

A)  2,2-dimethylpropane 
B)  2,2-dimethylbutane 
C)  2,3-dimethylbutane 
D)  2-methylpropane 
A)  2,2-dimethylpropane 
B)  2,2-dimethylbutane 
C)  2,3-dimethylbutane 
D)  2-methylpropane

Question 8

Which of the following is the most stable radical?

Accepted Answer

A)  
  
B)  
  
C)  
  
D)  
  
A)  
  
B)  
  
C)  
  
D)

Question 9

Chlorination of pentane gives a mixture of isomers having the molecular formula $\mathrm{C}_{5} \mathrm{H}_{11} \mathrm{Cl}$. The percentage of 1 -chloropentane is $22 \%$. Assuming the secondary hydrogens in pentane are equally reactive to monochlorination, what is the percentage of 3-chloropentane in the mixture?

Accepted Answer

A)  $48 \%$ 
B)  $26 \%$ 
C)  $22 \%$ 
D)  $14 \%$ 
A)  $48 \%$ 
B)  $26 \%$ 
C)  $22 \%$ 
D)  $14 \%$

Question 10

Arrange the following carbocations in order of their decreasing stabilities (most stable first).

Accepted Answer

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

Question 11

Arrange the following alcohols in order of their decreasing reactivity with $\mathrm{HBr}$ (most reactive first).

Accepted Answer

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

Which of the following mechanistically depicts the protonation of tert-butyl alcohol by hydrogen bromide?

Dibromination of isopropylcyclopentane gives a product which can be isolated in good yields. Which of the following would you predict to be this product?

The central carbon of the tert-butyl carbocation, $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}^{+}$ , is

What is the IUPAC name of the compound below?

If the compound below containing three types of alcohols were exposed to ONLY 1 equivalent of $\mathrm{HCl}$ , what major product would you expect? $If the compound below containing three types of alcohols were exposed to ONLY 1 equivalent of \mathrm{HCl} , what major product would you expect?$

What are the products of the following reaction?

Which one of the following gives a single monochlorination product?

Which of the following is the most stable radical?

Arrange the following carbocations in order of their decreasing stabilities (most stable first).

Arrange the following alcohols in order of their decreasing reactivity with $\mathrm{HBr}$ (most reactive first). $Arrange the following alcohols in order of their decreasing reactivity with \mathrm{HBr} (most reactive first).$

Structure Determines Properties

Alkanes and Cycloakanes: Introduction to Hydrocarbons

Alkanes and Cycloalkanes: Introduction to Stereochemistry

Structure and Preparation of Alkenes: Elimination Reactions

Addition Reactions of Alkenes

Chirality

Nucleophilic Substitution

Alkynes

Spectroscopy

Organometallic Compounds

Alcohols, Diols, and Thiols

Ethers, Epoxides, and Sulfides

Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl Group

Carboxylic Acids

Acid Derivatives

Enols and Enolates

Amines

Phenols

Carbohydrates

Lipids

Amino Acids, Peptides, and Proteins

Nucleosides, Nucleotides, and Nucleic Acids

Synthetic Polymers

Filters

Exam 4: Alcohols and Alkyl Halides: Introduction to Reaction Mechanisms

Which of the following mechanistically depicts the protonation of tert-butyl alcohol by hydrogen bromide?

Dibromination of isopropylcyclopentane gives a product which can be isolated in good yields. Which of the following would you predict to be this product?

The central carbon of the tert-butyl carbocation, (CH3)3C+\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}^{+}(CH3​)3​C+ , is

What is the IUPAC name of the compound below?

If the compound below containing three types of alcohols were exposed to ONLY 1 equivalent of HCl\mathrm{HCl}HCl , what major product would you expect?

What are the products of the following reaction?

Which one of the following gives a single monochlorination product?

Which of the following is the most stable radical?

Arrange the following carbocations in order of their decreasing stabilities (most stable first).

Arrange the following alcohols in order of their decreasing reactivity with HBr\mathrm{HBr}HBr (most reactive first).

Structure Determines Properties

Alkanes and Cycloakanes: Introduction to Hydrocarbons

Alkanes and Cycloalkanes: Introduction to Stereochemistry

Structure and Preparation of Alkenes: Elimination Reactions

Addition Reactions of Alkenes

Chirality

Nucleophilic Substitution

Alkynes

Spectroscopy

Organometallic Compounds

Alcohols, Diols, and Thiols

Ethers, Epoxides, and Sulfides

Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl Group

Carboxylic Acids

Acid Derivatives

Enols and Enolates

Amines

Phenols

Carbohydrates

Lipids

Amino Acids, Peptides, and Proteins

Nucleosides, Nucleotides, and Nucleic Acids

Synthetic Polymers

Filters

The central carbon of the tert-butyl carbocation, $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}^{+}$ , is

If the compound below containing three types of alcohols were exposed to ONLY 1 equivalent of $\mathrm{HCl}$ , what major product would you expect? $If the compound below containing three types of alcohols were exposed to ONLY 1 equivalent of \mathrm{HCl} , what major product would you expect?$

Arrange the following alcohols in order of their decreasing reactivity with $\mathrm{HBr}$ (most reactive first). $Arrange the following alcohols in order of their decreasing reactivity with \mathrm{HBr} (most reactive first).$