Question 1

is properly named:

Accepted Answer

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

Question 2

Which compound would have the lowest boiling point?

Accepted Answer

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

Question 3

If cis-2-butene is treated with meta-chloroperbenzoic acid what is the final product?

Accepted Answer

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

Question 4

The conversion of   is best achieved through use of which of these reagents in a low temperature reaction?

Accepted Answer

A) Concd.HBr 
B) Br2 
C) NaBr,H2SO4 
D) PBr3 
E) HBr,peroxide 
A) Concd.HBr 
B) Br2 
C) NaBr,H2SO4 
D) PBr3 
E) HBr,peroxide

Question 5

The product(s)of the following reaction

Accepted Answer

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

Question 6

Assuming an overall exothermic process,select the potential energy diagram that best represents the following reaction:

Accepted Answer

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

Question 7

What is the relationship between alcohols I and II?   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

Which of the following could not be used to synthesize 2-bromopentane efficiently?

Accepted Answer

A) 1-Pentene + HBr $\to$ 
B) 2-Pentene + HBr $\to$ 
C) 2-Pentanol + HBr $\to$ 
D) 2-Pentanol + PBr3 $\to$ 
E) All of these choices would afford good yields of 2-bromopentane. 
A) 1-Pentene + HBr $\to$ 
B) 2-Pentene + HBr $\to$ 
C) 2-Pentanol + HBr $\to$ 
D) 2-Pentanol + PBr3 $\to$ 
E) All of these choices would afford good yields of 2-bromopentane.

Question 9

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

Accepted Answer

A) different conformations of the same compound. 
B) constitutional isomers. 
C) enantiomers. 
D) diastereomers. 
E) identical. 
A) different conformations of the same compound. 
B) constitutional isomers. 
C) enantiomers. 
D) diastereomers. 
E) identical.

Question 10

What is the correct IUPAC name for the following compound?

Accepted Answer

A) 15-crown-5 
B) 15-crown-4 
C) 5-crown-15 
D) 15-crown-15 
E) Cyclopentadecane pentaether 
A) 15-crown-5 
B) 15-crown-4 
C) 5-crown-15 
D) 15-crown-15 
E) Cyclopentadecane pentaether

Question 11

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

Accepted Answer

A) CH3CH2CH=CH2 + HBr $\to$ 
B) CH3CH2CH2CH2OH + PBr3 $\to$ 
C) CH3CH2CH2(OH)CH3 + HBr $\to$ 
D) CH3CH2CH2CH2OH + Br2 $\to$ 
E) None of these choices. 
A) CH3CH2CH=CH2 + HBr $\to$ 
B) CH3CH2CH2CH2OH + PBr3 $\to$ 
C) CH3CH2CH2(OH)CH3 + HBr $\to$ 
D) CH3CH2CH2CH2OH + Br2 $\to$ 
E) None of these choices.

Question 12

Which compound would have the lowest boiling point?

Accepted Answer

A) CH3CH2CH2CH3 
B) CH3CH2OCH2CH3 
C) CH3CH2CH2OH 
D) (CH3)2CHOH 
E) HOCH2CH2OH 
A) CH3CH2CH2CH3 
B) CH3CH2OCH2CH3 
C) CH3CH2CH2OH 
D) (CH3)2CHOH 
E) HOCH2CH2OH

Question 13

A reaction which leads to a product of particular stereoisomeric outcome,depending on the stereochemistry of the reactant,is termed ___.

Accepted Answer

The answer of A reaction which leads to a product...

Question 14

is properly named:

Accepted Answer

A) cis-1,2-Cyclopentanediol 
B) meso-1,2-Cyclopentanediol 
C) (1R,2R)-1,2-Cyclopentanediol 
D) (1R,2S)-1,2-Cyclopentanediol 
E) (1S,2S)-1,2-Cyclopentanediol 
A) cis-1,2-Cyclopentanediol 
B) meso-1,2-Cyclopentanediol 
C) (1R,2R)-1,2-Cyclopentanediol 
D) (1R,2S)-1,2-Cyclopentanediol 
E) (1S,2S)-1,2-Cyclopentanediol

Question 15

Propose a mechanism for the following transformation:

Accepted Answer

The answer of Propose a mechanism for the following transformation:...

Question 16

is properly named:

Accepted Answer

A) 1,2-Cyclopentanediol 
B) 1,5-Cyclopentanediol 
C) (1R,2R)-1,2-Cyclopentanediol 
D) (1R,2S)-1,2-Cyclopentanediol 
E) (1S,2S)-1,2-Cyclopentanediol 
A) 1,2-Cyclopentanediol 
B) 1,5-Cyclopentanediol 
C) (1R,2R)-1,2-Cyclopentanediol 
D) (1R,2S)-1,2-Cyclopentanediol 
E) (1S,2S)-1,2-Cyclopentanediol

Question 17

What would be the major product of the following reaction sequence?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) An equimolar mixture of I and II. 
A) I 
B) II 
C) III 
D) IV 
E) An equimolar mixture of I and II.

Question 18

is properly named:

Accepted Answer

A) 1,3-Cyclopentanediol 
B) 1,4-Cyclopentanediol 
C) (1R,3R)-1,3-Cyclopentanediol 
D) (1R,3S)-1,3-Cyclopentanediol 
E) (1S,3S)-1,3-Cyclopentanediol 
A) 1,3-Cyclopentanediol 
B) 1,4-Cyclopentanediol 
C) (1R,3R)-1,3-Cyclopentanediol 
D) (1R,3S)-1,3-Cyclopentanediol 
E) (1S,3S)-1,3-Cyclopentanediol

Question 19

Heating 2-ethoxyhexane with one equivalent of concentrated HBr would produce:

Accepted Answer

A) CH3CH2OCH2CH2CH2CH2CH2CH2Br 
B) BrCH2CH2OCH2CH2CH2CH2CH2CH3 
C) CH3CH2OH and CH3CH2CH2CH2CHBrCH3 
D) CH3CH2Br and CH3CH2CH(OH)CH2CH2CH3 
E) CH3CH2Br and CH3CH2CH2CH2CH(OH)CH3 
A) CH3CH2OCH2CH2CH2CH2CH2CH2Br 
B) BrCH2CH2OCH2CH2CH2CH2CH2CH3 
C) CH3CH2OH and CH3CH2CH2CH2CHBrCH3 
D) CH3CH2Br and CH3CH2CH(OH)CH2CH2CH3 
E) CH3CH2Br and CH3CH2CH2CH2CH(OH)CH3

Question 20

If (Z)-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.

Exam 11: Alcohols and Ethers

is properly named:

Which compound would have the lowest boiling point?

If cis-2-butene is treated with meta-chloroperbenzoic acid what is the final product?

The conversion of is best achieved through use of which of these reagents in a low temperature reaction?

The product(s)of the following reaction

Assuming an overall exothermic process,select the potential energy diagram that best represents the following reaction:

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

Which of the following could not be used to synthesize 2-bromopentane efficiently?

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

What is the correct IUPAC name for the following compound?

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

Which compound would have the lowest boiling point?

A reaction which leads to a product of particular stereoisomeric outcome,depending on the stereochemistry of the reactant,is termed ___.

is properly named:

Propose a mechanism for the following transformation:

is properly named:

What would be the major product of the following reaction sequence?

is properly named:

Heating 2-ethoxyhexane with one equivalent of concentrated HBr would produce:

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

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

Heating 2-ethoxyhexanewith one equivalent of concentrated HBr would produce: