Question 1

The major product expected from the sequential reaction of cyclopentene with Br2/H2O,followed by sodium hydroxide is:

Accepted Answer

A) I 
B) II 
C) III 
D) IV + enantiomer 
E) None of these choices. 
A) I 
B) II 
C) III 
D) IV + enantiomer 
E) None of these choices.

Question 2

Which of the following could be used to synthesize 1-bromopentane?

Accepted Answer

A) CH3CH2CH2CH=CH2 + HBr $\to$ 
B) CH3CH2CH2CH2CH2OH + PBr3 $\to$ 
C) CH3CH2CH2CH2CH2OH + NaBr $\to$ 
D) CH3CH2CH2CH2CH2OH + Br2 $\to$ 
E) CH3CH2CH2CH=CH2 + Br2 $\to$ 
A) CH3CH2CH2CH=CH2 + HBr $\to$ 
B) CH3CH2CH2CH2CH2OH + PBr3 $\to$ 
C) CH3CH2CH2CH2CH2OH + NaBr $\to$ 
D) CH3CH2CH2CH2CH2OH + Br2 $\to$ 
E) CH3CH2CH2CH=CH2 + Br2 $\to$

Question 3

If (E)-2-pentene is treated with meta-chloroperbenzoic acid what is the final product?

Accepted Answer

A) I + enantiomer 
B) II + enantiomer 
C) III + enantiomer 
D) All of these choices. 
E) None of these choices. 
A) I + enantiomer 
B) II + enantiomer 
C) III + enantiomer 
D) All of these choices. 
E) None of these choices.

Question 4

Which would be the best way to carry out the following synthesis?

Accepted Answer

A) (1)HA,heat; (2)H3O+,H2O,heat 
B) (1)(CH3)3COK / (CH3)3COH; (2)BH3:THF,then H2O2,OH- 
C) (1)(CH3)3COK / (CH3)3COH; (2)H3O+,then H2O,heat 
D) (1)KOH,C2H5OH; (2)BH3:THF,then H2O2,OH- 
E) (1)KOH,C2H5OH; (2)HA,heat; (3)H3O+,H2O,heat 
A) (1)HA,heat; (2)H3O+,H2O,heat 
B) (1)(CH3)3COK / (CH3)3COH; (2)BH3:THF,then H2O2,OH- 
C) (1)(CH3)3COK / (CH3)3COH; (2)H3O+,then H2O,heat 
D) (1)KOH,C2H5OH; (2)BH3:THF,then H2O2,OH- 
E) (1)KOH,C2H5OH; (2)HA,heat; (3)H3O+,H2O,heat

Question 5

Finish the following acid-base reaction and predict if it will proceed in the forward direction:

Accepted Answer

The answer of Finish the following acid-base reaction and predict...

Question 6

If trans-2-bromocyclohexanol is treated with sodium hydroxide what is the major product?

Accepted Answer

A) I + enantiomer 
B) II + enantiomer 
C) III 
D) IV + enantiomer 
E) None of these choices. 
A) I + enantiomer 
B) II + enantiomer 
C) III 
D) IV + enantiomer 
E) None of these choices.

Question 7

What is the relationship between (1R,2S)-2-methylcycloheptanol and (1R,2R)-2-methylcycloheptanol? They are:

Accepted Answer

A) constitutional isomers. 
B) enantiomers. 
C) conformers 
D) diastereomers. 
E) identical. 
A) constitutional isomers. 
B) enantiomers. 
C) conformers 
D) diastereomers. 
E) identical.

Question 8

What is the relationship between alcohols I and II?   They are:

Accepted Answer

A) conformers. 
B) constitutional isomers. 
C) enantiomers. 
D) diastereomers. 
E) identical. 
A) conformers. 
B) constitutional isomers. 
C) enantiomers. 
D) diastereomers. 
E) identical.

Question 9

is properly named:

Accepted Answer

A) 1,2-Cyclohexanediol 
B) 1,6-Cyclohexanediol 
C) (1R,2R)-1,2-Cyclohexanediol 
D) (1R,2S)-1,2-Cyclohexanediol 
E) (1S,2S)-1,2-Cyclohexanediol 
A) 1,2-Cyclohexanediol 
B) 1,6-Cyclohexanediol 
C) (1R,2R)-1,2-Cyclohexanediol 
D) (1R,2S)-1,2-Cyclohexanediol 
E) (1S,2S)-1,2-Cyclohexanediol

Question 10

Which of the following can be described as "optically active,primary alcohol"?

Accepted Answer

A) CH3CH2CH2CH2CH2OH 
B) (CH3)2CHCH2CH2OH 
C) CH3CH2CH(CH3)CH2OH 
D) (CH3)2CHCHOHCH3 
E) Two of these choices. 
A) CH3CH2CH2CH2CH2OH 
B) (CH3)2CHCH2CH2OH 
C) CH3CH2CH(CH3)CH2OH 
D) (CH3)2CHCHOHCH3 
E) Two of these choices.

Question 11

The number of tertiary alcohols corresponding to the formula C5H12O,counting stereoisomers separately,is:

Accepted Answer

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

Question 12

What is the total number of pentyl alcohols,including stereoisomers?

Accepted Answer

A) 7 
B) 8 
C) 9 
D) 10 
E) 11 
A) 7 
B) 8 
C) 9 
D) 10 
E) 11

Question 13

The major industrial process in use today for the production of methanol is the:

Accepted Answer

A) hydration of ethyne. 
B) distillation of wood. 
C) hydrogenation of carbon dioxide. 
D) reduction of methanal. 
E) catalytic reduction of carbon monoxide. 
A) hydration of ethyne. 
B) distillation of wood. 
C) hydrogenation of carbon dioxide. 
D) reduction of methanal. 
E) catalytic reduction of carbon monoxide.

Question 14

Complete the following reaction sequence,giving structures for compounds C and D:

Accepted Answer

The answer of Complete the following reaction sequence,giving structures for...

Question 15

The reaction between 4-methyl-1-pentanol and PBr3 to yield 1-bromo-4-methylpentane is probably:

Accepted Answer

A) an SN1-type reaction involving the protonated alkyl dibomophosphite of the alcohol as the substrate. 
B) an SN2-type reaction involving the protonated alkyl dibomophosphite of the alcohol as the substrate. 
C) an E1-type reaction involving the protonated alkyl dibomophosphite of the alcohol as the substrate. 
D) an E2-type reaction involving the protonated alkyl dibomophosphite of the alcohol as the substrate. 
E) an epoxidation reaction. 
A) an SN1-type reaction involving the protonated alkyl dibomophosphite of the alcohol as the substrate. 
B) an SN2-type reaction involving the protonated alkyl dibomophosphite of the alcohol as the substrate. 
C) an E1-type reaction involving the protonated alkyl dibomophosphite of the alcohol as the substrate. 
D) an E2-type reaction involving the protonated alkyl dibomophosphite of the alcohol as the substrate. 
E) an epoxidation reaction.

Question 16

What is the relationship between alcohols I and II?   They are:

Accepted Answer

A) conformers. 
B) constitutional isomers. 
C) enantiomers. 
D) diastereomers. 
E) identical. 
A) conformers. 
B) constitutional isomers. 
C) enantiomers. 
D) diastereomers. 
E) identical.

Exam 11: Alcohols and Ethers

The major product expected from the sequential reaction of cyclopentene with Br2/H2O,followed by sodium hydroxide is:

Which of the following could be used to synthesize 1-bromopentane?

If (E)-2-pentene is treated with meta-chloroperbenzoic acid what is the final product?

Which would be the best way to carry out the following synthesis?

Finish the following acid-base reaction and predict if it will proceed in the forward direction:

If trans-2-bromocyclohexanol is treated with sodium hydroxide what is the major product?

What is the relationship between (1R,2S)-2-methylcycloheptanol and (1R,2R)-2-methylcycloheptanol? They are:

What is the relationship between alcohols I and II? They are:

is properly named:

Which of the following can be described as "optically active,primary alcohol"?

The number of tertiary alcohols corresponding to the formula C5H12O,counting stereoisomers separately,is:

What is the total number of pentyl alcohols,including stereoisomers?

The major industrial process in use today for the production of methanol is the:

Complete the following reaction sequence,giving structures for compounds C and D:

The reaction between 4-methyl-1-pentanol and PBr3 to yield 1-bromo-4-methylpentane is probably:

What is the relationship between alcohols I and II? They are:

The Basics

Families of Carbon

Acids and Bases

Nomenclature and Conformations of Alkanes and Cycloalkanes

Stereochemistry

Nucleophilic Reactions

Alkenes and Alkynes I

Alkenes and Alkynes II

Nuclear Magnetic Resonance and Mass Spectrometry

Radical Reactions

Alcohols From Carbonyl Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Reactions at the Α Carbon of Carbonyl Compounds

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

Amines

Transition Metal Complexes

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

The major product expected from the sequential reaction of cyclopentene with Br₂/H₂O,followed by sodium hydroxide is:

The number of tertiary alcohols corresponding to the formula C₅H₁₂O,counting stereoisomers separately,is:

The reaction between 4-methyl-1-pentanol and PBr₃ to yield 1-bromo-4-methylpentane is probably: