Question 1

Which of the following would be a reasonable synthesis of CH3CH2CH2CH2OH?

Accepted Answer

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

Question 2

Which is the best way to prepare 3-methoxypentane via the Williamson method?

Accepted Answer

A) CH3OH + CH3CH2CHOHCH2CH3 + H2SO4,140 S1U1P1$\circ$S1S1P0C 
B) CH3OH + (CH3)2CHCH2CH2OH + H2SO4,140 S1U1P1$\circ$S1S1P0C 
C) CH3ONa + (CH3CH2)2CHBr 
D) CH3I + (CH3CH2)2CHONa 
E) CH3I + (CH3)2CHCH2CH2ONa 
A) CH3OH + CH3CH2CHOHCH2CH3 + H2SO4,140 S1U1P1$\circ$S1S1P0C 
B) CH3OH + (CH3)2CHCH2CH2OH + H2SO4,140 S1U1P1$\circ$S1S1P0C 
C) CH3ONa + (CH3CH2)2CHBr 
D) CH3I + (CH3CH2)2CHONa 
E) CH3I + (CH3)2CHCH2CH2ONa

Question 3

Which is the best method to prepare ethoxycyclopentane via the Williamson method?

Accepted Answer

The answer of Which is the best method to prepare...

Question 4

Provide a reasonable synthetic strategy for the synthesis of trans-2-methoxycyclopentanol from bromocyclopentane

Accepted Answer

The answer of Provide a reasonable synthetic strategy for the...

Question 5

Stereochemically speaking,conversion of an alcohol into a tosylate occurs with ___ of configuration.

Accepted Answer

The answer of Stereochemically speaking,conversion of an alcohol into a...

Question 6

What is the correct IUPAC name for the following compound?

Accepted Answer

A) 4-isopropyl-3,4-dimethyl-2-butanol 
B) 2,3,4-trimethyl-4-pentanol 
C) 1,1,2,3-tetramethyl-4-pentanol 
D) 3,4,5-trimethyl-2-hexanol 
E) 3,4,5,5-tetramethyl-2-pentanol 
A) 4-isopropyl-3,4-dimethyl-2-butanol 
B) 2,3,4-trimethyl-4-pentanol 
C) 1,1,2,3-tetramethyl-4-pentanol 
D) 3,4,5-trimethyl-2-hexanol 
E) 3,4,5,5-tetramethyl-2-pentanol

Question 7

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 8

The oxymercuration-demercuration procedure can be successfully employed for synthesis of deuterated derivatives,by using NaBD4 instead of NaBH4 in the second step.What product would you expect from 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 9

Which compound would have the highest 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 10

The reaction between 2-methyl-2-pentanol and HBr to yield 2-methyl-2-pentene 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 11

Which compound would have the highest boiling point?

Accepted Answer

A) CH3CH2CH2CH3 
B) CH2(OH)CH(OH)CH2OH 
C) CH3CH2CH2OH 
D) (CH3)2CHOH 
E) HOCH2CH2OH 
A) CH3CH2CH2CH3 
B) CH2(OH)CH(OH)CH2OH 
C) CH3CH2CH2OH 
D) (CH3)2CHOH 
E) HOCH2CH2OH

Question 12

Which of these ethers is least likely to undergo significant cleavage by hot aqueous H2SO4?

Accepted Answer

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

Question 13

The reaction between 2-methyl-2-pentanol and HBr to yield 2-bromo-2-methylpentane 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 14

2,2-Dimethyl-1-propanol has the common name:

Accepted Answer

A) Isoamyl alcohol 
B) Isopentyl alcohol 
C) tert-Pentyl alcohol 
D) Neopentyl alcohol 
E) 2-Methylisobutyl alcohol 
A) Isoamyl alcohol 
B) Isopentyl alcohol 
C) tert-Pentyl alcohol 
D) Neopentyl alcohol 
E) 2-Methylisobutyl alcohol

Question 15

Which is a correct IUPAC name for CH3CH2OCH2CH2CH2OCH2CH3?

Accepted Answer

A) 1,4-Dioxane 
B) Ethylene glycol diethyl ether 
C) 1,3-Diethoxypropane 
D) 1,2-Diethoxyethane 
E) 1,2-Diethoxymethane 
A) 1,4-Dioxane 
B) Ethylene glycol diethyl ether 
C) 1,3-Diethoxypropane 
D) 1,2-Diethoxyethane 
E) 1,2-Diethoxymethane

Question 16

What is a correct IUPAC name for the following compound?

Accepted Answer

A) 1,2-butanediol 
B) isopropanol 
C) 1-propanol 
D) 1,2-propanediol 
E) ethylene glycol 
A) 1,2-butanediol 
B) isopropanol 
C) 1-propanol 
D) 1,2-propanediol 
E) ethylene glycol

Question 17

Supply the missing structures A and B.

Accepted Answer

The answer of Supply the missing structures A and B....

Question 18

Propose a structure for the compound with the following formula that is consistent with the IR and 1H NMR data shown:
C4H10O
IR - 1125cm−1,strong,broad
6H triplet at 1.2 $\delta$,J = 7 Hz
4H quartet at 3.7 $\delta$,J = 7 Hz

Accepted Answer

The answer of Propose a structure for the compound with...

Question 19

Today,most industrial ethanol is made in the U.S.by the:

Accepted Answer

A) fermentation of grain. 
B) hydrolysis of ethyl bromide. 
C) hydration of ethylene. 
D) reduction of acetaldehyde. 
E) hydration of acetylene. 
A) fermentation of grain. 
B) hydrolysis of ethyl bromide. 
C) hydration of ethylene. 
D) reduction of acetaldehyde. 
E) hydration of acetylene.

Question 20

What is the relationship between (1S,3R)-3-methylcyclohexanol and (1R,2R)-2-methylcyclohexanol? 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.

Exam 11: Alcohols and Ethers

Which of the following would be a reasonable synthesis of CH3CH2CH2CH2OH?

Which is the best way to prepare 3-methoxypentane via the Williamson method?

Which is the best method to prepare ethoxycyclopentane via the Williamson method?

Provide a reasonable synthetic strategy for the synthesis of trans-2-methoxycyclopentanol from bromocyclopentane

Stereochemically speaking,conversion of an alcohol into a tosylate occurs with ___ of configuration.

What is the correct IUPAC name for the following compound?

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

The oxymercuration-demercuration procedure can be successfully employed for synthesis of deuterated derivatives,by using NaBD4 instead of NaBH4 in the second step.What product would you expect from the following reaction?

Which compound would have the highest boiling point?

The reaction between 2-methyl-2-pentanol and HBr to yield 2-methyl-2-pentene is probably:

Which compound would have the highest boiling point?

Which of these ethers is least likely to undergo significant cleavage by hot aqueous H2SO4?

The reaction between 2-methyl-2-pentanol and HBr to yield 2-bromo-2-methylpentane is probably:

2,2-Dimethyl-1-propanol has the common name:

Which is a correct IUPAC name for CH3CH2OCH2CH2CH2OCH2CH3?

What is a correct IUPAC name for the following compound?

Supply the missing structures A and B.

Propose a structure for the compound with the following formula that is consistent with the IR and 1H NMR data shown: C4H10O IR - 1125cm−1,strong,broad 6H triplet at 1.2 δ\deltaδ ,J = 7 Hz 4H quartet at 3.7 δ\deltaδ ,J = 7 Hz

Today,most industrial ethanol is made in the U.S.by the:

What is the relationship between (1S,3R)-3-methylcyclohexanol and (1R,2R)-2-methylcyclohexanol? 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

Which of the following would be a reasonable synthesis of CH₃CH₂CH₂CH₂OH?

The oxymercuration-demercuration procedure can be successfully employed for synthesis of deuterated derivatives,by using NaBD₄ instead of NaBH₄ in the second step.What product would you expect from the following reaction?

Which of these ethers is least likely to undergo significant cleavage by hot aqueous H₂SO₄?

Which is a correct IUPAC name for CH₃CH₂OCH₂CH₂CH₂OCH₂CH₃?

Propose a structure for the compound with the following formula that is consistent with the IR and ¹H NMR data shown: C₄H₁₀O IR - 1125cm⁻¹,strong,broad 6H triplet at 1.2 $\delta$ ,J = 7 Hz 4H quartet at 3.7 $\delta$ ,J = 7 Hz