Question 1

What is the common name of the following compound?

Accepted Answer

A) Methyl sec-butyl ether 
B) Isobutyl methyl ether 
C) sec-Butyl methyl ether 
D) Butyl methyl ether 
A) Methyl sec-butyl ether 
B) Isobutyl methyl ether 
C) sec-Butyl methyl ether 
D) Butyl methyl ether

Question 2

What is the major product of the following reaction?

Accepted Answer

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

Question 3

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

Accepted Answer

A) (±)-2-Chlorobutane 
B) (R)-2-Chlorobutane 
C) (S)-2-Chlorobutane 
D) trans-2-Butene 
A) (±)-2-Chlorobutane 
B) (R)-2-Chlorobutane 
C) (S)-2-Chlorobutane 
D) trans-2-Butene

Question 4

Which of the following compounds are epoxides?

Accepted Answer

A) Only I and III 
B) Only III and IV 
C) Only I,III,and IV 
D) I,II,III,and IV 
A) Only I and III 
B) Only III and IV 
C) Only I,III,and IV 
D) I,II,III,and IV

Question 5

What is the IUPAC name of the following compound?

Accepted Answer

A) 5-Ethylthio-4-isopropylpentane 
B) 1-Ethylthio-3-methyl-2-propylbutane 
C) 1-Ethylthio-2-isopropylpentane 
D) Isooctylthioethane 
A) 5-Ethylthio-4-isopropylpentane 
B) 1-Ethylthio-3-methyl-2-propylbutane 
C) 1-Ethylthio-2-isopropylpentane 
D) Isooctylthioethane

Question 6

What is the major organic product(s)obtained in the following reaction?

Accepted Answer

A) I 
B) II 
C) III 
D) I and II 
A) I 
B) II 
C) III 
D) I and II

Question 7

What is the major organic product of the following reaction?

Accepted Answer

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

Question 8

What is the IUPAC name of the following compound?

Accepted Answer

A) (2R,4R)-4-chloro-2-pentanol 
B) (2R,4S)-4-chloro-2-pentanol 
C) (2S,4R)-4-chloro-2-pentanol 
D) (2S,4S)-4-chloro-2-pentanol 
A) (2R,4R)-4-chloro-2-pentanol 
B) (2R,4S)-4-chloro-2-pentanol 
C) (2S,4R)-4-chloro-2-pentanol 
D) (2S,4S)-4-chloro-2-pentanol

Question 9

What is the IUPAC of the following compound?

Accepted Answer

A) 1,1-Dimethyloxirane 
B) 2-Methylpropylane 
C) 2-Methylpropylene oxide 
D) 2,2-Dimethyloxirane 
A) 1,1-Dimethyloxirane 
B) 2-Methylpropylane 
C) 2-Methylpropylene oxide 
D) 2,2-Dimethyloxirane

Question 10

Which of the following statements about carbocation rearrangement is not true?

Accepted Answer

A) A less stable carbocation can rearrange to a more stable carbocation by shift of a hydrogen atom. 
B) A less stable carbocation can rearrange to a more stable carbocation by shift of an alkyl group. 
C) 1,2-Shifts convert a less stable carbocation to a more stable carbocation. 
D) The migrating group in a 1,2-shift moves with one bonding electron. 
A) A less stable carbocation can rearrange to a more stable carbocation by shift of a hydrogen atom. 
B) A less stable carbocation can rearrange to a more stable carbocation by shift of an alkyl group. 
C) 1,2-Shifts convert a less stable carbocation to a more stable carbocation. 
D) The migrating group in a 1,2-shift moves with one bonding electron.

Question 11

What is the IUPAC of the following compound?

Accepted Answer

A) 5-Hydroxy-3-methyl-1-pentene 
B) 3-Methyl-5-penten-1-ol 
C) 3-Methyl-1-penten-5-ol 
D) 3-Methyl-4-penten-1-ol 
A) 5-Hydroxy-3-methyl-1-pentene 
B) 3-Methyl-5-penten-1-ol 
C) 3-Methyl-1-penten-5-ol 
D) 3-Methyl-4-penten-1-ol

Question 12

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

Accepted Answer

A) (R)-2-Methylpentanenitrile 
B) (S)-2-Methylpentanenitrile 
C) (±)-2-Methylpentanenitrile 
D) trans-2-Butene 
A) (R)-2-Methylpentanenitrile 
B) (S)-2-Methylpentanenitrile 
C) (±)-2-Methylpentanenitrile 
D) trans-2-Butene

Question 13

Which of the following ethers cannot be prepared by the Williamson ether synthesis?

Accepted Answer

A) Isopropyl methyl ether 
B) tert-Butyl methyl ether 
C) tert-Butyl phenyl ether 
D) Methyl phenyl ether 
A) Isopropyl methyl ether 
B) tert-Butyl methyl ether 
C) tert-Butyl phenyl ether 
D) Methyl phenyl ether

Question 14

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

Accepted Answer

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

Question 15

Which of the following compounds is (are)symmetrical ethers?

Accepted Answer

A) Only I 
B) Only IV 
C) Only III and IV 
D) Only I,III,and IV 
A) Only I 
B) Only IV 
C) Only III and IV 
D) Only I,III,and IV

Question 16

What is the IUPAC name of the following compound?

Accepted Answer

A) R-2,2-dimethylcyclohexanol 
B) S-2,2-dimethylcyclohexanol 
C) R-1,1-dimethyl-2-cyclohexanol 
D) S-1,1-dimethyl-2-cyclohexanol 
A) R-2,2-dimethylcyclohexanol 
B) S-2,2-dimethylcyclohexanol 
C) R-1,1-dimethyl-2-cyclohexanol 
D) S-1,1-dimethyl-2-cyclohexanol

Question 17

What are the major products obtained upon treatment of ethyl methyl ether with excess HBr?

Accepted Answer

A) Bromomethane and ethanol 
B) Bromoethane and methanol 
C) Bromoethane and bromomethane 
D) Ethanol and methanol 
A) Bromomethane and ethanol 
B) Bromoethane and methanol 
C) Bromoethane and bromomethane 
D) Ethanol and methanol

Question 18

What is the IUPAC of the following compound? (CH3CH2)3COH

Accepted Answer

A) 2-Ethyl-2-pentanol 
B) 2-Ethyl-3-pentanol 
C) 3-Ethyl-3-pentanol 
D) 2,2-Diethyl-1-butanol 
A) 2-Ethyl-2-pentanol 
B) 2-Ethyl-3-pentanol 
C) 3-Ethyl-3-pentanol 
D) 2,2-Diethyl-1-butanol

Question 19

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

Accepted Answer

A) HCl 
B) H2SO4 
C) NaOH 
D) TsCl,pyridine 
A) HCl 
B) H2SO4 
C) NaOH 
D) TsCl,pyridine

Question 20

Which of the following explains why epoxides are much more reactive than ethers?

Accepted Answer

A) The C-O-C bond angle of an epoxide is 109°,making epoxides to have angle strain. 
B) The oxygen atom of an epoxide is sp2 hybridized. 
C) The C-O-C bond angle of an epoxide is 120°,making epoxides to have angle strain. 
D) The C-O-C bond angle of an epoxide is 60°,making epoxides to have angle strain. 
A) The C-O-C bond angle of an epoxide is 109°,making epoxides to have angle strain. 
B) The oxygen atom of an epoxide is sp2 hybridized. 
C) The C-O-C bond angle of an epoxide is 120°,making epoxides to have angle strain. 
D) The C-O-C bond angle of an epoxide is 60°,making epoxides to have angle strain.

Exam 9: Alcohols,ethers,and Related Compounds

What is the common name of the following compound?

What is the major product of the following reaction?

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

Which of the following compounds are epoxides?

What is the IUPAC name of the following compound?

What is the major organic product(s)obtained in the following reaction?

What is the major organic product of the following reaction?

What is the IUPAC name of the following compound?

What is the IUPAC of the following compound?

Which of the following statements about carbocation rearrangement is not true?

What is the IUPAC of the following compound?

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

Which of the following ethers cannot be prepared by the Williamson ether synthesis?

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

Which of the following compounds is (are)symmetrical ethers?

What is the IUPAC name of the following compound?

What are the major products obtained upon treatment of ethyl methyl ether with excess HBr?

What is the IUPAC of the following compound? (CH3CH2)3COH

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

Which of the following explains why epoxides are much more reactive than ethers?

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Elimination Reactions

Alkenes and Addition Reactions

Alkynes and Synthesis

Oxidation and Reduction

Radical Reactions

Conjugation,resonance,and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones - Nucleophilic Addition

Carboxylic Acids and the Acidity of the O-H Bond

Carboxylic Acids and Their Derivatives Nucleophilic Acyl Substitution

Substitution Reactions of Carbonyl Compounds at the a Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond-Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

Spectroscopy A: Mass Spectrometry

Spectroscopy B: Infrared Spectroscopy

Spectroscopy C: Nuclear Magnetic Resonance Spectroscopy

Filters

What is the IUPAC of the following compound? (CH₃CH₂)₃COH