Question 1

Which of the reagents listed below would serve as the basis for a simple chemical test to distinguish between

Accepted Answer

A) AgNO3 in alcohol 
B) NaOH in H2O 
C) Br2 in CCl4 
D) Cold conc.H2SO4 
E) KMnO4 in H2O 
A) AgNO3 in alcohol 
B) NaOH in H2O 
C) Br2 in CCl4 
D) Cold conc.H2SO4 
E) KMnO4 in H2O

Question 2

Which is the best method to prepare 2-ethoxy-5-methylhexane?

Accepted Answer

A) C2H5ONa + (CH3)2CHCH2CH2Br 
B) C2H5ONa + (CH3)2CHCH2CH2CH2CH2Br 
C) C2H5ONa + (CH3)2CHCH2CH2CHBrCH3 
D) C2H5Br + (CH3)2CHCH2CH2CH(CH3)ONa 
E)    
A) C2H5ONa + (CH3)2CHCH2CH2Br 
B) C2H5ONa + (CH3)2CHCH2CH2CH2CH2Br 
C) C2H5ONa + (CH3)2CHCH2CH2CHBrCH3 
D) C2H5Br + (CH3)2CHCH2CH2CH(CH3)ONa 
E)

Question 3

The following reaction,   is probably:

Accepted Answer

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

Question 4

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 5

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 6

Complete the following reaction sequence,giving structural details of all key intermediates:

Accepted Answer

The answer of Complete the following reaction sequence,giving structural details...

Question 7

Which reaction can accomplish the following transformation in good yield:

Accepted Answer

A) H+/H2O 
B) oxymercuration/demercuration 
C) hydroboration/oxidation 
D) reaction with NaOH 
E) none of these choices 
A) H+/H2O 
B) oxymercuration/demercuration 
C) hydroboration/oxidation 
D) reaction with NaOH 
E) none of these choices

Question 8

The total number of secondary alcohols corresponding to the formula C6H14O,ignoring stereoisomers,is:

Accepted Answer

A) 2 
B) 4 
C) 6 
D) 8 
E) 10 
A) 2 
B) 4 
C) 6 
D) 8 
E) 10

Question 9

Which of the following would be a reasonable synthesis of 2-butanol?

Accepted Answer

A)    
B)    
C)    
D)    
E) None of these choices. 
A)    
B)    
C)    
D)    
E) None of these choices.

Question 10

What would be the major product(s)of the following reaction

Accepted Answer

A) C6H5Br + CH3OH 
B) C6H5CH2Br + CH3Br 
C) C6H5CH2OH + CH3Br 
D) C6H5CH2Br + CH3OH 
E) C6H5CH2CH2Br 
A) C6H5Br + CH3OH 
B) C6H5CH2Br + CH3Br 
C) C6H5CH2OH + CH3Br 
D) C6H5CH2Br + CH3OH 
E) C6H5CH2CH2Br

Question 11

The number of primary 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

The total number of secondary alcohols corresponding to the formula C4H10O,counting stereoisomers separately,is:

Accepted Answer

A) 1 
B) 2 
C) 3 
D) 4 
E) No secondary alcohols can be made from this formula 
A) 1 
B) 2 
C) 3 
D) 4 
E) No secondary alcohols can be made from this formula

Question 13

Draw the structures of all the products formed when (R)-3-methylcyclopentene is subjected to the hydroboration-oxidation sequence.

Accepted Answer

The alkene is symmetrically su

Question 14

Propose a mechanism for the following transformation:

Accepted Answer

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

Question 15

Which compound would have the highest boiling point?

Accepted Answer

A) CH3CH2CH2CH3 
B) CH3CH2OCH3 
C) CH3CH2CH2OH 
D) (CH3)2CHOH 
E) HOCH2CH2OH 
A) CH3CH2CH2CH3 
B) CH3CH2OCH3 
C) CH3CH2CH2OH 
D) (CH3)2CHOH 
E) HOCH2CH2OH

Question 16

Which of the following could be used to synthesize 2-chlorobutane?

Accepted Answer

A) CH3CH2CH$\equiv$CH2 + Cl2(aq)$\to$ 
B) CH3CH2CHOHCH3 + HCl $\to$ 
C) CH3CH2C$\equiv$CH + HCl $\to$ 
D) CH3CH2C$\equiv$CH + Cl2 $\to$ 
E) None of these choices. 
A) CH3CH2CH$\equiv$CH2 + Cl2(aq)$\to$ 
B) CH3CH2CHOHCH3 + HCl $\to$ 
C) CH3CH2C$\equiv$CH + HCl $\to$ 
D) CH3CH2C$\equiv$CH + Cl2 $\to$ 
E) None of these choices.

Question 17

Draw all of the optically active alcohols corresponding to the formula C5H12O.

Accepted Answer

Question 18

Which of these,though often used,is an incorrect common name for (CH3)3COH?

Accepted Answer

A) tert-Butyl alcohol 
B) tert-Butanol 
C) 2-Methyl-2-propanol 
D) More than one is incorrect. 
E) Each is a correct name. 
A) tert-Butyl alcohol 
B) tert-Butanol 
C) 2-Methyl-2-propanol 
D) More than one is incorrect. 
E) Each is a correct name.

Question 19

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 20

Draw all of the ethers corresponding to the formula C5H12O,including stereoisomers.

Accepted Answer

Exam 11: Alcohols and Ethers

Which of the reagents listed below would serve as the basis for a simple chemical test to distinguish between

Which is the best method to prepare 2-ethoxy-5-methylhexane?

The following reaction, is probably:

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

Which compound would have the lowest boiling point?

Complete the following reaction sequence,giving structural details of all key intermediates:

Which reaction can accomplish the following transformation in good yield:

The total number of secondary alcohols corresponding to the formula C6H14O,ignoring stereoisomers,is:

Which of the following would be a reasonable synthesis of 2-butanol?

What would be the major product(s)of the following reaction

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

The total number of secondary alcohols corresponding to the formula C4H10O,counting stereoisomers separately,is:

Draw the structures of all the products formed when (R)-3-methylcyclopentene is subjected to the hydroboration-oxidation sequence.

Propose a mechanism for the following transformation:

Which compound would have the highest boiling point?

Which of the following could be used to synthesize 2-chlorobutane?

Draw all of the optically active alcohols corresponding to the formula C5H12O.

Which of these,though often used,is an incorrect common name for (CH3)3COH?

is properly named:

Draw all of the ethers corresponding to the formula C5H12O,including stereoisomers.

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 total number of secondary alcohols corresponding to the formula C₆H₁₄O,ignoring stereoisomers,is:

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

The total number of secondary alcohols corresponding to the formula C₄H₁₀O,counting stereoisomers separately,is:

Draw all of the optically active alcohols corresponding to the formula C₅H₁₂O.

Which of these,though often used,is an incorrect common name for (CH₃)₃COH?

Draw all of the ethers corresponding to the formula C₅H₁₂O,including stereoisomers.