Question 1

Which of the following reactions would yield 3,3-dimethyl-1-butene in a reasonable percentage yield (i.e.,greater than 50%)?

Accepted Answer

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

Question 2

What would you expect to be the chief organic product(s)when 2-bromo-2-methylpentane react(s)with sodium propynide,i.e.,

Accepted Answer

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

Question 3

Which of these compounds would give the largest E2/SN2 product ratio on reaction with sodium ethoxide in ethanol at 55°C?

Accepted Answer

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

Question 4

Which one of the following alcohols would dehydrate most rapidly when treated with sulfuric acid?

Accepted Answer

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

Question 5

Which statement is/are true about acetylide anions?

Accepted Answer

A) The alkylated product is poor with secondary alkyl halides. 
B) Primary alkyl halides are best suited for alkylation. 
C) In the presence of tertiary alkyl halides,the acetylide anion acts as base to give an elimination product. 
D) Only two of these statements are true. 
E) All of the statements are true. 
A) The alkylated product is poor with secondary alkyl halides. 
B) Primary alkyl halides are best suited for alkylation. 
C) In the presence of tertiary alkyl halides,the acetylide anion acts as base to give an elimination product. 
D) Only two of these statements are true. 
E) All of the statements are true.

Question 6

Rearrangements are likely to occur in which of the following reaction types?

Accepted Answer

A) SN1 reactions 
B) SN2 reactions 
C) E1 reactions 
D) E2 reactions 
E) Both SN1 and E1 reactions 
A) SN1 reactions 
B) SN2 reactions 
C) E1 reactions 
D) E2 reactions 
E) Both SN1 and E1 reactions

Question 7

What are the major product(s)formed when trans-1-bromo-2-methylcyclohexane reacts with sodium isopropoxide in isopropanol?

Accepted Answer

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

Question 8

The correct IUPAC name for the following compound is:

Accepted Answer

A) (
E) -2-Bromo-3-chloro-5-methyl-2-hexene 
B) (
E) -2-Bromo-3-chloro-5-methyl-3-hexene 
C) (Z)-2-Bromo-3-chloro-5-methyl-3-hexene 
D) (Z)-2-Bromo-3-chloro-5-methyl-2-hexene 
E) (
E) -2-Methyl-5-bromo-4-chloro-4-hexene 
A) (
E) -2-Bromo-3-chloro-5-methyl-2-hexene 
B) (
E) -2-Bromo-3-chloro-5-methyl-3-hexene 
C) (Z)-2-Bromo-3-chloro-5-methyl-3-hexene 
D) (Z)-2-Bromo-3-chloro-5-methyl-2-hexene 
E) (
E) -2-Methyl-5-bromo-4-chloro-4-hexene

Question 9

Which of the following methods could be used to synthesize 4,4-dimethyl-2-hexyne?

Accepted Answer

A)    
B)    
C)    
D) More than one of these choices. 
E) None of these choices. 
A)    
B)    
C)    
D) More than one of these choices. 
E) None of these choices.

Question 10

If 0.10 mol of HSCH2CH2OH reacts at 25S1U1P1$\circ$S1S1P0C,sequentially,with 0.20 mol of NaH,0.10 mol of CH3CH2Br followed by the addition of H2O,which is the major product?

Accepted Answer

A) HSCH2CH2OCH2CH3 
B) CH3CH2SCH2CH2OH 
C) CH3CH2SCH2CH2OCH2CH3 
D) CH2=CH2 
E) CH3CH3 
A) HSCH2CH2OCH2CH3 
B) CH3CH2SCH2CH2OH 
C) CH3CH2SCH2CH2OCH2CH3 
D) CH2=CH2 
E) CH3CH3

Question 11

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

Question 12

When 0.10 mol of ICH2CH2CH2CH2Cl reacts with 0.10 mol of NaOCH3 in CH3OH at 40S1U1P1$\circ$S1S1P0C,the major product is:

Accepted Answer

A) CH3OCH2CH2CH2CH2Cl 
B) CH3OCH2CH2CH2CH2I 
C) CH3OCH2CH2CH2CH2OCH3 
D) CH2=CHCH2CH2Cl 
E) CH2=CHCH2CH2I 
A) CH3OCH2CH2CH2CH2Cl 
B) CH3OCH2CH2CH2CH2I 
C) CH3OCH2CH2CH2CH2OCH3 
D) CH2=CHCH2CH2Cl 
E) CH2=CHCH2CH2I

Question 13

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

Accepted Answer

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

Question 14

Which reaction would not result in alkylation of the acetylide anion as the major products?

Accepted Answer

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

Question 15

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

Accepted Answer

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

Question 16

Which alkyl halide,when treated with sodium ethoxide in ethanol,would afford a product mixture consisting of more than one elimination product?

Accepted Answer

A) 1-bromo-3,3-dimethylpentane 
B) 1-bromo-2,3-dimethylpentane 
C) 2-bromo-3,4-dimethylpentane 
D) 2-bromo-3,3-dimethylpentane 
E) None of these choices would yield more than one elimination product. 
A) 1-bromo-3,3-dimethylpentane 
B) 1-bromo-2,3-dimethylpentane 
C) 2-bromo-3,4-dimethylpentane 
D) 2-bromo-3,3-dimethylpentane 
E) None of these choices would yield more than one elimination product.

Question 17

What are the major product(s)formed when cis-1-bromo-2-methylcyclohexane reacts with sodium isopropoxide in isopropanol?

Accepted Answer

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

Question 18

Elimination reactions are favored over nucleophilic substitution reactions

Accepted Answer

A) at high temperatures. 
B) when tert-butoxide ion is used. 
C) when 3S1U1P1$\circ$S1S1P0 alkyl halides are used as substrates. 
D) when nucleophiles are used which are strong bases and the substrate is a 2S1U1P1$\circ$S1S1P0alkyl halide. 
E) in all of these cases. 
A) at high temperatures. 
B) when tert-butoxide ion is used. 
C) when 3S1U1P1$\circ$S1S1P0 alkyl halides are used as substrates. 
D) when nucleophiles are used which are strong bases and the substrate is a 2S1U1P1$\circ$S1S1P0alkyl halide. 
E) in all of these cases.

Question 19

Which of the following compounds could be produced from the following reaction sequence?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) mixture of III and IV 
A) I 
B) II 
C) III 
D) IV 
E) mixture of III and IV

Question 20

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

Accepted Answer

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

Exam 7: Alkenes and Alkynes I

Which of the following reactions would yield 3,3-dimethyl-1-butene in a reasonable percentage yield (i.e.,greater than 50%)?

What would you expect to be the chief organic product(s)when 2-bromo-2-methylpentane react(s)with sodium propynide,i.e.,

Which of these compounds would give the largest E2/SN2 product ratio on reaction with sodium ethoxide in ethanol at 55°C?

Which one of the following alcohols would dehydrate most rapidly when treated with sulfuric acid?

Which statement is/are true about acetylide anions?

Rearrangements are likely to occur in which of the following reaction types?

What are the major product(s)formed when trans-1-bromo-2-methylcyclohexane reacts with sodium isopropoxide in isopropanol?

The correct IUPAC name for the following compound is:

Which of the following methods could be used to synthesize 4,4-dimethyl-2-hexyne?

If 0.10 mol of HSCH2CH2OH reacts at 25 ∘\circ∘ C,sequentially,with 0.20 mol of NaH,0.10 mol of CH3CH2Br followed by the addition of H2O,which is the major product?

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

When 0.10 mol of ICH2CH2CH2CH2Cl reacts with 0.10 mol of NaOCH3 in CH3OH at 40 ∘\circ∘ C,the major product is:

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

Which reaction would not result in alkylation of the acetylide anion as the major products?

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

Which alkyl halide,when treated with sodium ethoxide in ethanol,would afford a product mixture consisting of more than one elimination product?

What are the major product(s)formed when cis-1-bromo-2-methylcyclohexane reacts with sodium isopropoxide in isopropanol?

Elimination reactions are favored over nucleophilic substitution reactions

Which of the following compounds could be produced from the following reaction sequence?

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

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

Which of these compounds would give the largest E2/S_N2 product ratio on reaction with sodium ethoxide in ethanol at 55°C?

If 0.10 mol of HSCH₂CH₂OH reacts at 25^$\circ$C,sequentially,with 0.20 mol of NaH,0.10 mol of CH₃CH₂Br followed by the addition of H₂O,which is the major product?

When 0.10 mol of ICH₂CH₂CH₂CH₂Cl reacts with 0.10 mol of NaOCH₃ in CH₃OH at 40^$\circ$C,the major product is: