Question 1

What is the IUPAC name of the following compound?

Accepted Answer

(R)-2-methylhex-5-en-3-ol

Question 2

What is the major organic product obtained from the following reaction?

Accepted Answer

The answer of What is the major organic product obtained...

Question 3

The pKa of CH3CH2CH2OH is _______than that of CH3CH2CH2SH.

Accepted Answer

less
smaller

Question 4

What is the best choice of reagent to achieve the following transformation?

Accepted Answer

A)  CrO3 
B)  NaOH 
C)  PCC 
D)  HIO4 
A)  CrO3 
B)  NaOH 
C)  PCC 
D)  HIO4

Question 5

What is the major organic product obtained from the following sequence of reactions?

Accepted Answer

A)  (±)-2-azidopentane 
B)  (R)-2-azidopentane 
C)  (S)-2-azidopentane 
D)  (S)-2-pentyl tosylate 
A)  (±)-2-azidopentane 
B)  (R)-2-azidopentane 
C)  (S)-2-azidopentane 
D)  (S)-2-pentyl tosylate

Question 6

Which of the following alcohols reacts fastest with HBr to give the corresponding alkyl bromide?

Accepted Answer

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

Question 7

What type of reactive intermediate is formed in the reaction of tert-butyl alcohol with H2SO4 to give methylpropene?

Accepted Answer

A)  tert-butyl cation 
B)  tert-butyl anion 
C)  tert-butyl radical 
D)  tert-butoxide 
A)  tert-butyl cation 
B)  tert-butyl anion 
C)  tert-butyl radical 
D)  tert-butoxide

Question 8

Oxidation of ethanol by chromic acid produces ethanoic acid, which is commonly known as acetic acid. In the course of the reaction, ethanol is first converted to acetaldehyde. Then, hydration of acetaldehyde produces "X", which bears two hydroxyl groups. "X" reacts with the chromic acid in the presence of an acid catalyst to form "Y". A base reacts with "Y" to produce acetic acid. Identify "X" and "Y".

Accepted Answer

A)  X is propanal hydrate, and Y is ethyl chromate ester. 
B)  X is formaldehyde hydrate, and Y is ethyl chromate ester. 
C)  X is acetaldehyde hydrate, and Y is propyl chromate ester. 
D)  X is acetaldehyde hydrate, and Y is ethyl chromate ester. 
A)  X is propanal hydrate, and Y is ethyl chromate ester. 
B)  X is formaldehyde hydrate, and Y is ethyl chromate ester. 
C)  X is acetaldehyde hydrate, and Y is propyl chromate ester. 
D)  X is acetaldehyde hydrate, and Y is ethyl chromate ester.

Question 9

What is the major organic product obtained from the following reaction?

Accepted Answer

The answer of What is the major organic product obtained...

Question 10

Which of the following alcohols undergoes the most rapid dehydration upon treatment with H2SO4 to give an alkene?

Accepted Answer

A)  methanol 
B)  ethanol 
C)  2-propanol 
D)  2-methyl-2-propanol 
A)  methanol 
B)  ethanol 
C)  2-propanol 
D)  2-methyl-2-propanol

Question 11

What is the correct assignment of the names of the following functional groups?

Accepted Answer

A)  1 = thiol; 2 = sulfone; 3 = sulfoxide 
B)  1 = thiol; 2 = sulfoxide; 3 = sulfone 
C)  1 = thiol; 2 = sulfinic acid; 3 = sulfonic acid 
D)  1 = sulfonic acid; 2 = sulfone; 3 = sulfinic acid 
A)  1 = thiol; 2 = sulfone; 3 = sulfoxide 
B)  1 = thiol; 2 = sulfoxide; 3 = sulfone 
C)  1 = thiol; 2 = sulfinic acid; 3 = sulfonic acid 
D)  1 = sulfonic acid; 2 = sulfone; 3 = sulfinic acid

Question 12

(CH3)3CO- Na+ would be formed by the reaction of sodium metal and 1-butanol.

Accepted Answer

A) True 
 B)False

Question 13

What is the major organic product obtained from the following reaction?

Accepted Answer

The answer of What is the major organic product obtained...

Question 14

What is the major organic product obtained from the following reaction? $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{SH} \stackrel { I_2 } { \longrightarrow }$

Accepted Answer

The answer of What is the major organic product obtained...

Question 15

What is the major organic product obtained from the following reaction?

Accepted Answer

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

Question 16

What is the major organic product obtained from the following reaction?

Accepted Answer

The answer of What is the major organic product obtained...

Question 17

Of the following compounds, 3 would have the highest boiling point. 1. $ \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCH}_{3}$$\quad$$\quad$2. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}$$\quad$$\quad$$\quad$3. $\begin{array}{c}
\mathrm{CH}_{3} \mathrm{CHCH}_{3}\|\\mathrm{OH}
\end{array}$

Accepted Answer

A) True 
 B)False

Question 18

Which of the following is/are primary (1°) alcohols?

Accepted Answer

A)  only 1 
B)  only 3 
C)  only 1 and 3 
D)  only 2, 3, and 4 
A)  only 1 
B)  only 3 
C)  only 1 and 3 
D)  only 2, 3, and 4

Question 19

(CH3)3COH would react faster than (CH3)2CHCH2OH under SN1 conditions.

Accepted Answer

A) True 
 B)False

Question 20

Why can't tertiary alcohols be oxidized to ketones or aldehydes?

Accepted Answer

The prerequisite for the oxidation of al

Exam 10: Alcohols

What is the IUPAC name of the following compound?

What is the major organic product obtained from the following reaction?

The pKa of CH3CH2CH2OH is _______than that of CH3CH2CH2SH.

What is the best choice of reagent to achieve the following transformation?

What is the major organic product obtained from the following sequence of reactions?

Which of the following alcohols reacts fastest with HBr to give the corresponding alkyl bromide?

What type of reactive intermediate is formed in the reaction of tert-butyl alcohol with H2SO4 to give methylpropene?

What is the major organic product obtained from the following reaction?

Which of the following alcohols undergoes the most rapid dehydration upon treatment with H2SO4 to give an alkene?

What is the correct assignment of the names of the following functional groups?

(CH3)3CO- Na+ would be formed by the reaction of sodium metal and 1-butanol.

What is the major organic product obtained from the following reaction?

What is the major organic product obtained from the following reaction? CH3CH2SH⟶I2\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{SH} \stackrel { I_2 } { \longrightarrow }CH3​CH2​SH⟶I2​​

What is the major organic product obtained from the following reaction?

What is the major organic product obtained from the following reaction?

Of the following compounds, 3 would have the highest boiling point. 1. CH3CH2OCH3 \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCH}_{3}CH3​CH2​OCH3​\quad\quad 2. CH3CH2CH2OH\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}CH3​CH2​CH2​OH\quad\quad\quad 3. |

Which of the following is/are primary (1°) alcohols?

(CH3)3COH would react faster than (CH3)2CHCH2OH under SN1 conditions.

Why can't tertiary alcohols be oxidized to ketones or aldehydes?

Covalent Bonding and Shapes of Molecules

Alkanes and Cycloalkanes

Stereoisomerism and Chirality

Acids and Bases

Alkenes: Bonding, Nomenclature, and Properties

Reactions of Alkenes

Alkynes

Haloalkanes, Halogenation, and Radical Reactions

Nucleophilic Substitution and Beta-Elimination

Ethers, Epoxides, and Sulfides

Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Mass Spectrometry

An Introduction to Organometallic Compounds

Aldehydes and Ketones

Carboxylic Acids

Functional Derivatives of Carboxylic Acids

Enolate Anions and Enamines

Dienes, Conjugated Systems, and Pericyclic Reactions

Benzene and the Concept of Aromaticity

Reactions of Benzene and Its Derivatives

Amines

Catalytic Carbon-Carbon Bond Formation

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids

Organic Polymer Chemistry

Filters

The pK_a of CH₃CH₂CH₂OH is _______than that of CH₃CH₂CH₂SH.

What type of reactive intermediate is formed in the reaction of tert-butyl alcohol with H₂SO₄ to give methylpropene?

Which of the following alcohols undergoes the most rapid dehydration upon treatment with H₂SO₄ to give an alkene?

(CH₃)₃CO^- Na⁺ would be formed by the reaction of sodium metal and 1-butanol.

What is the major organic product obtained from the following reaction? $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{SH} \stackrel { I_2 } { \longrightarrow }$

Of the following compounds, 3 would have the highest boiling point. 1. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCH}_{3}$ $\quad$ $\quad$ 2. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}$ $\quad$ $\quad$ $\quad$ 3. |

(CH₃)₃COH would react faster than (CH₃)₂CHCH₂OH under S_N1 conditions.