Question 1

What is the major product for the following reaction?

Accepted Answer

A)    
B)    
C)    
D)    
E) More than one of these choices. 
A)    
B)    
C)    
D)    
E) More than one of these choices.

Question 2

Consider the substitution reaction that takes place when (R)-3-bromo-3-methylhexane is treated with sodium methoxide.Which of the following would be true?

Accepted Answer

A) An SN2 reaction would take place with inversion of configuration at the stereogenic center. 
B) An SN1 reaction would take place with retention of configuration at the stereogenic center. 
C) An SN1 reaction would take place with racemization of configuration at the stereogenic center. 
D) An SN1 reaction would take place,accompanied by an E1 reaction,affording a complex mixture of products. 
E) An E2 reaction would take place,during which the stereogenic center is lost. 
A) An SN2 reaction would take place with inversion of configuration at the stereogenic center. 
B) An SN1 reaction would take place with retention of configuration at the stereogenic center. 
C) An SN1 reaction would take place with racemization of configuration at the stereogenic center. 
D) An SN1 reaction would take place,accompanied by an E1 reaction,affording a complex mixture of products. 
E) An E2 reaction would take place,during which the stereogenic center is lost.

Question 3

Conversion of alkynes to E-alkenes (trans-alkenes)can be accomplished via a ___ reaction.

Accepted Answer

dissolving

Question 4

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

Accepted Answer

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

Question 6

What would be the major product obtained when trans-1-bromo-3-methylcyclopentane is allowed to react with NaSH at 25oC?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) Equal amounts of I and II. 
A) I 
B) II 
C) III 
D) IV 
E) Equal amounts of I and II.

Question 7

Propose a reasonable synthetic strategy for the synthesis of trans-6-methyl-3-heptene from 4-methyl-1-pentyne.

Accepted Answer

@#IMG-DLM& Step 1: Add NaNH₂/NH₃(l)to selectively de

Question 8

When tert-pentyl chloride undergoes solvolysis in aqueous ethanol at room temperature,there is/are formed:

Accepted Answer

A)    
B)    
C)    
D)    
E) All of these choices. 
A)    
B)    
C)    
D)    
E) All of these choices.

Question 9

What is the major product for 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 10

What is the major product for the following reaction?

Accepted Answer

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

Question 11

Predict the major organic product(s)of the following reaction:

Accepted Answer

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

Question 12

Predict the product(s)for 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 13

How will you prepare cis-1,2-dimethylcyclohexane from 1,2-dimethylcyclohexene?

Accepted Answer

Catalytic

Question 14

What is the major product for the following reaction?

Accepted Answer

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

Question 15

The structure of the product obtained from 2-butyne and Li/C2H5NH2 is:

Accepted Answer

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

Question 16

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 17

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

Accepted Answer

A) SN1 
B) SN2 
C) E1 
D) E2 
E) More than one of the above 
A) SN1 
B) SN2 
C) E1 
D) E2 
E) More than one of the above

Question 18

Propose a two-step synthetic strategy for the synthesis of 2-methylhexane from 5-methyl-2-hexanol.

Accepted Answer

@#IMG-DLM& Step 1:
Acid-catalyzed dehydration of 5

Question 19

Name the following compound:

Accepted Answer

A) (S,
E) -2,4-dibromo-3-methylpent-2-ene 
B) (R,Z)-2,4-dibromo-3-methylpent-2-ene 
C) (R,
E) -2,4-dibromo-3-methylpent-3-ene 
D) (S,
E) -2,4-dibromo-3-methylpent-3-ene 
E) (R,
E) -2,4-dibromo-3-methylpent-2-ene 
A) (S,
E) -2,4-dibromo-3-methylpent-2-ene 
B) (R,Z)-2,4-dibromo-3-methylpent-2-ene 
C) (R,
E) -2,4-dibromo-3-methylpent-3-ene 
D) (S,
E) -2,4-dibromo-3-methylpent-3-ene 
E) (R,
E) -2,4-dibromo-3-methylpent-2-ene

Question 20

Which structure represents (E)-1-bromo-2-methylhex-2-ene?

Accepted Answer

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

Exam 7: Alkenes and Alkynes I

What is the major product for the following reaction?

Consider the substitution reaction that takes place when (R)-3-bromo-3-methylhexane is treated with sodium methoxide.Which of the following would be true?

Conversion of alkynes to E-alkenes (trans-alkenes)can be accomplished via a ___ reaction.

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

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

What would be the major product obtained when trans-1-bromo-3-methylcyclopentane is allowed to react with NaSH at 25oC?

Propose a reasonable synthetic strategy for the synthesis of trans-6-methyl-3-heptene from 4-methyl-1-pentyne.

When tert-pentyl chloride undergoes solvolysis in aqueous ethanol at room temperature,there is/are formed:

What is the major product for the following reaction sequence?

What is the major product for the following reaction?

Predict the major organic product(s)of the following reaction:

Predict the product(s)for the following reaction sequence.

How will you prepare cis-1,2-dimethylcyclohexane from 1,2-dimethylcyclohexene?

What is the major product for the following reaction?

The structure of the product obtained from 2-butyne and Li/C2H5NH2 is:

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

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

Propose a two-step synthetic strategy for the synthesis of 2-methylhexane from 5-methyl-2-hexanol.

Name the following compound:

Which structure represents (E)-1-bromo-2-methylhex-2-ene?

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

What would be the major product obtained when trans-1-bromo-3-methylcyclopentane is allowed to react with NaSH at 25^oC?

The structure of the product obtained from 2-butyne and Li/C₂H₅NH₂ is: