Question 1

Predict the two most likely mechanisms for the reaction of 2-iodohexane with sodium ethoxide.

Accepted Answer

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

Question 2

How many different types of  hydrogens are present in the following molecule?

Accepted Answer

A) 0 
B) 1 
C) 2 
D) 3 
E) 4 
A) 0 
B) 1 
C) 2 
D) 3 
E) 4

Question 3

Which of the following alkyl halides forms the most stable carbocation when it undergoes an E1 reaction?

Accepted Answer

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

Question 4

Provide the structure of the major organic product of the following reaction.

Accepted Answer

The answer of Provide the structure of the major organic...

Question 5

Give the mechanism of the reaction shown below.

Accepted Answer

The answer of Give the mechanism of the reaction shown...

Question 6

Which of the following carbocations does not rearrange?

Accepted Answer

A)    
B)    
C)    
D)    
E) all the above 
A)    
B)    
C)    
D)    
E) all the above

Question 7

Which diastereomer of 1-bromo-4-t-butylcyclohexane,the cis or the trans,undergoes elimination more rapidly when treated with sodium ethoxide? Explain your answer.

Accepted Answer

The cis isomer reacts more quickly.An ax

Question 8

Which of the following are the substitution products of the reaction shown below? CH3CH2Br + -OH → ?

Accepted Answer

A) CH3CH2BrH+ + O- 
B) HOCH2CH2Br 
C) CH3CH2OH + Br- 
D) CH2     CH2 + Br- + H2O 
E) CH2     CHBr + H2O 
A) CH3CH2BrH+ + O- 
B) HOCH2CH2Br 
C) CH3CH2OH + Br- 
D) CH2     CH2 + Br- + H2O 
E) CH2     CHBr + H2O

Question 9

Which base,ammonia (NH3)or triethylamine [(CH3CH2)3N],would be a better choice for use in converting 1-chlorohexane to 1-hexene? Explain briefly.

Accepted Answer

Triethylamine.Amines can serve as both n

Question 10

Give the major product for the following E2 reaction.

Accepted Answer

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

Question 11

Draw the product of the following reaction.

Accepted Answer

The answer of Draw the product of the following reaction....

Question 12

What is the major product which results when (2R,3S)-2-chloro-3-phenylbutane is treated with sodium methoxide in methanol?

Accepted Answer

A) (
E) -2-phenyl-2-butene 
B) (Z)-2-phenyl-2-butene 
C) (S)-3-phenyl-1-butene 
D) (R)-3-phenyl-1-butene 
E) (R)-2-methoxy-2-phenylbutane 
A) (
E) -2-phenyl-2-butene 
B) (Z)-2-phenyl-2-butene 
C) (S)-3-phenyl-1-butene 
D) (R)-3-phenyl-1-butene 
E) (R)-2-methoxy-2-phenylbutane

Question 13

Consider the following reaction mechanism:   What effect will the following have on the rate?
a.addition of Br-
b.using a more polar solvent
c.using a stronger nucleophile
d.using a more concentrated nucleophile

Accepted Answer

a.reaction will slow down because of com

Question 14

What mechanism predominates in the reaction below?

Accepted Answer

A) SN2 
B) SN1 without rearrangement 
C) SN1 with rearrangement 
D) E2 
E) E1 
A) SN2 
B) SN1 without rearrangement 
C) SN1 with rearrangement 
D) E2 
E) E1

Question 15

How would you convert 1-bromo-1,4,4-trimethylcyclohexane to the following compound?

Accepted Answer

The answer of How would you convert 1-bromo-1,4,4-trimethylcyclohexane to the...

Question 16

Give the major product for the E2 reaction.

Accepted Answer

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

Question 17

Provide the structure of the major organic product which results in the following reaction.

Accepted Answer

The answer of Provide the structure of the major organic...

Question 18

Which of the following solvents is protic?

Accepted Answer

A)    
B)    
C) CH3CH2OCH3 
D) CH3CH2OH 
E) CH3CH2CH2Cl 
A)    
B)    
C) CH3CH2OCH3 
D) CH3CH2OH 
E) CH3CH2CH2Cl

Question 19

Which of the following correctly describes SAM,a biological methylating agent?

Accepted Answer

A) It contains a Cl bonded to a 1° carbon. 
B) It contains a methyl group bonded to a positively charged sulfur atom. 
C) It contains a methyl ether. 
D) it contains a methyl group bonded to an aromatic ring. 
E) It contains a Br bonded to a phosphorus atom. 
A) It contains a Cl bonded to a 1° carbon. 
B) It contains a methyl group bonded to a positively charged sulfur atom. 
C) It contains a methyl ether. 
D) it contains a methyl group bonded to an aromatic ring. 
E) It contains a Br bonded to a phosphorus atom.

Question 20

In the SN1 hydrolysis mechanism of (CH3)3CBr,there are ________ elementary steps,________ distinct transition states,and ________ distinct intermediates.

Accepted Answer

A) 2,2,2 
B) 2,2,3 
C) 2,3,2 
D) 3,2,3 
E) 3,3,2 
A) 2,2,2 
B) 2,2,3 
C) 2,3,2 
D) 3,2,3 
E) 3,3,2

Exam 9: Substitution and Elimination Reactions of Alkyl Halides

Predict the two most likely mechanisms for the reaction of 2-iodohexane with sodium ethoxide.

How many different types of  hydrogens are present in the following molecule?

Which of the following alkyl halides forms the most stable carbocation when it undergoes an E1 reaction?

Provide the structure of the major organic product of the following reaction.

Give the mechanism of the reaction shown below.

Which of the following carbocations does not rearrange?

Which diastereomer of 1-bromo-4-t-butylcyclohexane,the cis or the trans,undergoes elimination more rapidly when treated with sodium ethoxide? Explain your answer.

Which of the following are the substitution products of the reaction shown below? CH3CH2Br + -OH → ?

Which base,ammonia (NH3)or triethylamine [(CH3CH2)3N],would be a better choice for use in converting 1-chlorohexane to 1-hexene? Explain briefly.

Give the major product for the following E2 reaction.

Draw the product of the following reaction.

What is the major product which results when (2R,3S)-2-chloro-3-phenylbutane is treated with sodium methoxide in methanol?

Consider the following reaction mechanism: What effect will the following have on the rate? a.addition of Br- b.using a more polar solvent c.using a stronger nucleophile d.using a more concentrated nucleophile

What mechanism predominates in the reaction below?

How would you convert 1-bromo-1,4,4-trimethylcyclohexane to the following compound?

Give the major product for the E2 reaction.

Provide the structure of the major organic product which results in the following reaction.

Which of the following solvents is protic?

Which of the following correctly describes SAM,a biological methylating agent?

In the SN1 hydrolysis mechanism of (CH3)3CBr,there are ________ elementary steps,________ distinct transition states,and ________ distinct intermediates.

Remembering General Chemistry: Electronic Structure and Bonding

Acids and Bases: Central to Understanding Organic Chemistry

An Introduction to Organic Compounds: Nomenclature, physical Properties, and Structure

Isomers: the Arrangement of Atoms in Space

Alkenes: Structure,nomenclature,and an Introduction to Reactivity - Thermodynamics and Kinetics

The Reactions of Alkenes - the Stereochemistry of Addition Reactions

The Reactions of Alkynes - Introduction to Multistep Synthesis

Delocalized Electrons: Their Effect on Stability, pka, and the Products of a Reaction - Aromaticity and Electronic Effects: an Introduction to the Reactions of Benzene

Reactions of Alcohols, ethers, epoxides, amines and Sulfur-Containing Compounds

Organometallic Compounds

Radicals

Mass Spectrometry,infrared Spectroscopy,and Uvvis Spectroscopy

Nmr Spectroscopy

Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Reactions of Aldehydes and Ketones

Reactions at the Α-Carbon

Reactions of Benzene and Substituted Benzenes

More About Amines - Reactions of Heterocylic Compounds

The Organic Chemistry of Carbohydrates

Amino Acids,peptides,and Proteins

Catalysis in Organic Reactions and in Enzymatic Reactions

The Organic Chemistry of the Coenzymes, compounds Derived From Vitamins

The Organic Chemistry of the Metabolic Pathways

The Organic Chemistry of Lipids

The Chemistry of the Nucleic Acids

Synthetic Polymers

Pericyclic Reactions

Filters

Which of the following are the substitution products of the reaction shown below? CH₃CH₂Br + ^-OH → ?

Which base,ammonia (NH₃)or triethylamine [(CH₃CH₂)₃N],would be a better choice for use in converting 1-chlorohexane to 1-hexene? Explain briefly.

Consider the following reaction mechanism: What effect will the following have on the rate? a.addition of Br^- b.using a more polar solvent c.using a stronger nucleophile d.using a more concentrated nucleophile

In the S_N1 hydrolysis mechanism of (CH₃)₃CBr,there are elementary steps, distinct transition states,and distinct intermediates.