Question 1

Name the following compound:

Accepted Answer

A) (S,
E) -3-chlorohex-4-en-1-yne 
B) (R,
E) -3-chlorohex-2-en-5-yne 
C) (S,
E) -3-chlorohex-2-en-5-yne 
D) (R,
E) -3-chlorohex-4-en-1-yne 
E) (R,
E) -3-chloropent-4-en-1-yne 
A) (S,
E) -3-chlorohex-4-en-1-yne 
B) (R,
E) -3-chlorohex-2-en-5-yne 
C) (S,
E) -3-chlorohex-2-en-5-yne 
D) (R,
E) -3-chlorohex-4-en-1-yne 
E) (R,
E) -3-chloropent-4-en-1-yne

Question 2

Which of the following carbocations would NOT be likely to undergo rearrangement?

Accepted Answer

A)    
B)    
C)    
D)    
E)    
A)    
B)    
C)    
D)    
E)

Question 3

Syn hydrogenation of an alkyne will produce a ___ alkene.

Accepted Answer

The answer of Syn hydrogenation of an alkyne will produce...

Question 4

What is the major product(s)of the reaction of the following reaction sequence?

Accepted Answer

A)    
B)    
C)    
D)    
E) A mixture of two of these choices. 
A)    
B)    
C)    
D)    
E) A mixture of two of these choices.

Question 5

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

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) More than one of these choices. 
A) I 
B) II 
C) III 
D) IV 
E) More than one of these choices.

Question 6

Rank the following compounds from lowest to highest heat of hydrogenation:

Accepted Answer

A) I,II,III,IV 
B) IV,III,II,I 
C) II,III,IV,I 
D) I,IV,III,II 
E) none of these choices 
A) I,II,III,IV 
B) IV,III,II,I 
C) II,III,IV,I 
D) I,IV,III,II 
E) none of these choices

Question 7

Regarding the use of potassium tert-butoxide as a base in E2 reactions,it is incorrect to state that:

Accepted Answer

A) this base is more effective than ethoxide ion,because it (KOt-Bu)is the more basic of the two. 
B) it tends to give the anti-Zaitsev,i.e.,Hofmann,product. 
C) it is more reactive in dimethyl sulfoxide than it is in tert-butyl alcohol. 
D) it favors E2 reactions over competing SN2 reactions. 
E) it will form,predominantly,the more stable alkene. 
A) this base is more effective than ethoxide ion,because it (KOt-Bu)is the more basic of the two. 
B) it tends to give the anti-Zaitsev,i.e.,Hofmann,product. 
C) it is more reactive in dimethyl sulfoxide than it is in tert-butyl alcohol. 
D) it favors E2 reactions over competing SN2 reactions. 
E) it will form,predominantly,the more stable alkene.

Question 8

Complete the following reaction,giving structural details of all intermediates as well as the final product.

Accepted Answer

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

Question 9

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

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) More than one of these choices. 
A) I 
B) II 
C) III 
D) IV 
E) More than one of these choices.

Question 10

Name the following compound:

Accepted Answer

A) (cis)-3-methoxyhex-3-ene 
B) (Z)-4-methoxyhex-4-ene 
C) (Z)-3-methoxyhex-3-ene 
D) (
E) -3-methoxyhex-3-ene 
E) 3-methoxyhex-3-ene 
A) (cis)-3-methoxyhex-3-ene 
B) (Z)-4-methoxyhex-4-ene 
C) (Z)-3-methoxyhex-3-ene 
D) (
E) -3-methoxyhex-3-ene 
E) 3-methoxyhex-3-ene

Question 11

Upon catalytic hydrogenation with platinum,a compound C6H6 absorbs four moles of hydrogen.Select a structure for C6H6.

Accepted Answer

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

Question 12

The product(s)for the following reaction would mainly be dictated by which mechanism?

Accepted Answer

A) SN1 
B) SN2 
C) E1 
D) E2 
E) None of these choices. 
A) SN1 
B) SN2 
C) E1 
D) E2 
E) None of these choices.

Question 13

The major product(s)for the following reaction would mainly be dictated by which mechanism?

Accepted Answer

A) SN1 
B) SN2 
C) E1 
D) E2 
E) None of these choices. 
A) SN1 
B) SN2 
C) E1 
D) E2 
E) None of these choices.

Question 14

Write a retrosynthetic analysis of the compound cis-1-butenylcyclohexane from vinylcyclohexane and then write a forward synthesis showing all necessary reagents and relevant intermediates.

Accepted Answer

The answer of Write a retrosynthetic analysis of the compound...

Question 15

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

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) More than one of these choices. 
A) I 
B) II 
C) III 
D) IV 
E) More than one of these choices.

Question 16

By analyzing the starting material and the product(s),the following reaction is an example of what type of mechanism?

Accepted Answer

A) SN1 
B) SN2 
C) E1 
D) E2 
E) More than one of these choices. 
A) SN1 
B) SN2 
C) E1 
D) E2 
E) More than one of these choices.

Question 17

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

Accepted Answer

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

Question 18

What would be the major 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 19

You want to synthesize 3-methyl-2-pentene from 2-chloro-3-methylpentane.Which reagent would you use?

Accepted Answer

A) HCl,heat 
B) NH3(aq),25oC 
C) CH3CO2Na,CH3CO2H,heat 
D) CH3CH2ONa,CH3CH2OH,heat 
E) CH3CH2OH,heat 
A) HCl,heat 
B) NH3(aq),25oC 
C) CH3CO2Na,CH3CO2H,heat 
D) CH3CH2ONa,CH3CH2OH,heat 
E) CH3CH2OH,heat

Question 20

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

Accepted Answer

A) (CH3CH2)2C=C=CHT 
B) (CH3CH2)2C=C=CH2 
C) (CH3CH2)2CHCCT 
D) (CH3CH2)2CHCH=CHT 
E) None of these choices. 
A) (CH3CH2)2C=C=CHT 
B) (CH3CH2)2C=C=CH2 
C) (CH3CH2)2CHCCT 
D) (CH3CH2)2CHCH=CHT 
E) None of these choices.

Exam 7: Alkenes and Alkynes I

Name the following compound:

Which of the following carbocations would NOT be likely to undergo rearrangement?

Syn hydrogenation of an alkyne will produce a ___ alkene.

What is the major product(s)of the reaction of the following reaction sequence?

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

Rank the following compounds from lowest to highest heat of hydrogenation:

Regarding the use of potassium tert-butoxide as a base in E2 reactions,it is incorrect to state that:

Complete the following reaction,giving structural details of all intermediates as well as the final product.

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

Name the following compound:

Upon catalytic hydrogenation with platinum,a compound C6H6 absorbs four moles of hydrogen.Select a structure for C6H6.

The product(s)for the following reaction would mainly be dictated by which mechanism?

The major product(s)for the following reaction would mainly be dictated by which mechanism?

Write a retrosynthetic analysis of the compound cis-1-butenylcyclohexane from vinylcyclohexane and then write a forward synthesis showing all necessary reagents and relevant intermediates.

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

By analyzing the starting material and the product(s),the following reaction is an example of what type of mechanism?

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

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

You want to synthesize 3-methyl-2-pentene from 2-chloro-3-methylpentane.Which reagent would you use?

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

The Basics

Families of Carbon

Acids and Bases

Nomenclature and Conformations of Alkanes and Cycloalkanes

Stereochemistry

Nucleophilic Reactions

Alkenes and Alkynes II

Nuclear Magnetic Resonance and Mass Spectrometry

Radical Reactions

Alcohols and Ethers

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

Upon catalytic hydrogenation with platinum,a compound C₆H₆ absorbs four moles of hydrogen.Select a structure for C₆H₆.