Question 1

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

Accepted Answer

A) 4 
B) 5 
C) 6 
D) 7 
E) 18 
A) 4 
B) 5 
C) 6 
D) 7 
E) 18

Question 2

Which of the alcohols listed below would you expect to react most rapidly with PBr3?

Accepted Answer

A) CH3CH2CH2CH2CH2CH2OH 
B) (CH3CH2)2CH(OH)CH2CH3 
C) (CH3CH2)2CHOHCH3 
D) (CH3CH2)3COH 
E) (CH3CH2)2C(CH3)OH 
A) CH3CH2CH2CH2CH2CH2OH 
B) (CH3CH2)2CH(OH)CH2CH3 
C) (CH3CH2)2CHOHCH3 
D) (CH3CH2)3COH 
E) (CH3CH2)2C(CH3)OH

Question 3

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 4

Propose a structure for the compound with the following formula that is consistent with the IR and 1H NMR data shown:
C7H8O
IR - 3325cm−1,strong,broad
1H broad singlet at 2.3 $\delta$(exchangeable)
2H singlet at 4.6 $\delta$
5H multiplet at 7.3 $\delta$

Accepted Answer

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

Question 5

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 6

The relationship between a crown ether and the ion it transports is known as the ___ relationship.

Accepted Answer

The answer of The relationship between a crown ether and...

Question 7

Which compound (or compounds)would be produced when trans-2-butene is treated first with a peroxy acid to form an epoxide,and then the epoxide is subjected to acid-catalyzed hydrolysis?

Accepted Answer

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

Question 8

The hydroboration-oxidation procedure can be successfully employed for synthesis of deuterated derivatives,by using BD3 instead of BH3.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

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 10

Assuming the mechanistic pathway for each of the following reactions is predominately SN1,which of these alkyl halide syntheses is predicted to occur at the greatest rate?

Accepted Answer

A) CH3CH2CH2CH2OH + HI $\to$ 
B) (CH3)2CHCH2OH + HBr $\to$ 
C) CH3CHOHCH2CH3 + HCl $\to$ 
D) CH3CHOHCH2CH3 + HBr $\to$ 
E) (CH3)3COH + HI $\to$ 
A) CH3CH2CH2CH2OH + HI $\to$ 
B) (CH3)2CHCH2OH + HBr $\to$ 
C) CH3CHOHCH2CH3 + HCl $\to$ 
D) CH3CHOHCH2CH3 + HBr $\to$ 
E) (CH3)3COH + HI $\to$

Question 11

Give the correct IUPAC name corresponding to the following structure:

Accepted Answer

(R)-3-ethy

Question 12

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 13

Which compound is a mesylate?

Accepted Answer

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

Question 14

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

Accepted Answer

A) 6 
B) 8 
C) 10 
D) 12 
E) 14 
A) 6 
B) 8 
C) 10 
D) 12 
E) 14

Question 15

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 16

is properly named:

Accepted Answer

A) (S)-bicyclo[1.1.1]octan-2-ol 
B) (S)-bicyclo[2.2.2]octan-2-ol 
C) (R)-bicyclo[2.2.2]octan-2-ol 
D) (S)-bicyclo[2.2.2]octan-1-ol 
E) (S)-bicyclo[2.2.1]octan-2-ol 
A) (S)-bicyclo[1.1.1]octan-2-ol 
B) (S)-bicyclo[2.2.2]octan-2-ol 
C) (R)-bicyclo[2.2.2]octan-2-ol 
D) (S)-bicyclo[2.2.2]octan-1-ol 
E) (S)-bicyclo[2.2.1]octan-2-ol

Question 17

What is the major product of the reaction when (R)-3-methylcyclohexene is subjected to the hydroboration-oxidation sequence?

Accepted Answer

A) (1R,2R)-2-methylcyclohexanol + (1S,2R)-2-methylcyclohexanol 
B) (1S,2R)-2-methylcyclohexanol + (1S,2S)-2-methylcyclohexanol 
C) (1R,3R)-3-methylcyclohexanol + (1S,3R)-3-methylcyclohexanol 
D) (1S,3R)-3-methylcyclohexanol + (1S,3S)-3-methylcyclohexanol 
E) Two of these choices 
A) (1R,2R)-2-methylcyclohexanol + (1S,2R)-2-methylcyclohexanol 
B) (1S,2R)-2-methylcyclohexanol + (1S,2S)-2-methylcyclohexanol 
C) (1R,3R)-3-methylcyclohexanol + (1S,3R)-3-methylcyclohexanol 
D) (1S,3R)-3-methylcyclohexanol + (1S,3S)-3-methylcyclohexanol 
E) Two of these choices

Question 18

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 19

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 20

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

Accepted Answer

A) AgNO3 in C2H5OH 
B) Dilute HCl 
C) Br2 in CCl4 
D) NaOH in H2O 
E) KMnO4 in H2O 
A) AgNO3 in C2H5OH 
B) Dilute HCl 
C) Br2 in CCl4 
D) NaOH in H2O 
E) KMnO4 in H2O

Exam 11: Alcohols and Ethers

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

Which of the alcohols listed below would you expect to react most rapidly with PBr3?

The product(s)of the following reaction

Propose a structure for the compound with the following formula that is consistent with the IR and 1H NMR data shown: C7H8O IR - 3325cm−1,strong,broad 1H broad singlet at 2.3 δ\deltaδ (exchangeable) 2H singlet at 4.6 δ\deltaδ 5H multiplet at 7.3 δ\deltaδ

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

The relationship between a crown ether and the ion it transports is known as the ___ relationship.

Which compound (or compounds)would be produced when trans-2-butene is treated first with a peroxy acid to form an epoxide,and then the epoxide is subjected to acid-catalyzed hydrolysis?

The hydroboration-oxidation procedure can be successfully employed for synthesis of deuterated derivatives,by using BD3 instead of BH3.What product would you expect from the following reaction?

The product(s)of the following reaction

Assuming the mechanistic pathway for each of the following reactions is predominately SN1,which of these alkyl halide syntheses is predicted to occur at the greatest rate?

Give the correct IUPAC name corresponding to the following structure:

The following reaction, is probably:

Which compound is a mesylate?

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

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

is properly named:

What is the major product of the reaction when (R)-3-methylcyclohexene is subjected to the hydroboration-oxidation sequence?

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

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

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

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 primary alcohols corresponding to the formula C₆H₁₄O,ignoring stereoisomers,is:

Which of the alcohols listed below would you expect to react most rapidly with PBr₃?

Propose a structure for the compound with the following formula that is consistent with the IR and ¹H NMR data shown: C₇H₈O IR - 3325cm⁻¹,strong,broad 1H broad singlet at 2.3 $\delta$ (exchangeable) 2H singlet at 4.6 $\delta$ 5H multiplet at 7.3 $\delta$

The hydroboration-oxidation procedure can be successfully employed for synthesis of deuterated derivatives,by using BD₃ instead of BH₃.What product would you expect from the following reaction?

Assuming the mechanistic pathway for each of the following reactions is predominately S_N1,which of these alkyl halide syntheses is predicted to occur at the greatest rate?

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