Question 1

Predict the mechanism of the reaction and the reagent needed to carry out the following transformation.

Accepted Answer

The answer of Predict the mechanism of the reaction and...

Question 2

Why is the alkyl halide below not capable of undergoing an E2 reaction upon treatment with sodium ethoxide?

Accepted Answer

A) Br- is too poor a leaving group. 
B) The substrate is too hindered. 
C) Too much angle strain would be present in the alkene product. 
D) Sodium ethoxide is a poor base to use in E2 reactions. 
E) The C-H and C-Br bonds which need to break cannot achieve an anti-periplanar orientation. 
A) Br- is too poor a leaving group. 
B) The substrate is too hindered. 
C) Too much angle strain would be present in the alkene product. 
D) Sodium ethoxide is a poor base to use in E2 reactions. 
E) The C-H and C-Br bonds which need to break cannot achieve an anti-periplanar orientation.

Question 3

Which of the following halides is most reactive in an E2 reaction with sodium methoxide?

Accepted Answer

A) (CH3)3CCH2I 
B) (CH3)2CHCHICH3 
C) (CH3)2CHCH2Br 
D) (CH3)2CHCH2Cl 
E) (CH3)2CHCH2CH2Cl 
A) (CH3)3CCH2I 
B) (CH3)2CHCHICH3 
C) (CH3)2CHCH2Br 
D) (CH3)2CHCH2Cl 
E) (CH3)2CHCH2CH2Cl

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

The hydrolysis of tert-butyl chloride proceeds more rapidly in a solvent mixture which is 70% water/30% acetone than in one which is 30% water/70% acetone.Why?

Accepted Answer

A) The transition state in the carbocation formation step is better stabilized in the more polar solvent mixture. 
B) The reaction proceeds by an SN2 mechanism wherein the rate is increased by increasing the concentration of the nucleophile water. 
C) The reaction proceeds by an SN1 mechanism wherein the rate is increased by increasing the concentration of the nucleophile water. 
D) The solvent which contains a greater percentage of water is less polar,and this destabilizes the tert-butyl chloride. 
E) none of the above 
A) The transition state in the carbocation formation step is better stabilized in the more polar solvent mixture. 
B) The reaction proceeds by an SN2 mechanism wherein the rate is increased by increasing the concentration of the nucleophile water. 
C) The reaction proceeds by an SN1 mechanism wherein the rate is increased by increasing the concentration of the nucleophile water. 
D) The solvent which contains a greater percentage of water is less polar,and this destabilizes the tert-butyl chloride. 
E) none of the above

Question 6

Provide the major organic product(s)in the reaction below.

Accepted Answer

The answer of Provide the major organic product(s)in the reaction...

Question 7

Which of the following correctly reflects relative stabilities of carbocations?

Accepted Answer

A) 3° allylic > 2° > 1° benzylic 
B) methyl > 2° benzylic > 3° 
C) 3° benzylic > vinyl > 1° 
D) 2° allylic > 2° > vinyl 
E) 1° benzylic > 3° > 3° allylic 
A) 3° allylic > 2° > 1° benzylic 
B) methyl > 2° benzylic > 3° 
C) 3° benzylic > vinyl > 1° 
D) 2° allylic > 2° > vinyl 
E) 1° benzylic > 3° > 3° allylic

Question 8

What is/are the product(s)of the following reaction?

Accepted Answer

A)    
B) CH2     CH2 
C)    
D) A and B 
E) A and C 
A)    
B) CH2     CH2 
C)    
D) A and B 
E) A and C

Question 9

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 10

Draw the product of the following reaction.

Accepted Answer

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

Question 11

Provide the structure of the major organic product which results when 2-bromo-2-methylbutane is treated with sodium ethoxide.

Accepted Answer

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

Question 12

Name the products of the following SN2 reactions.

Accepted Answer

a)3-cyclopentyl-1-pr

Question 13

Give the major product for the following E1 reaction.

Accepted Answer

A)    
B)    
C)    
D)    
E) no reaction 
A)    
B)    
C)    
D)    
E) no reaction

Question 14

Which of the following alkyl halides undergoes E1 reactions with the fastest rate?

Accepted Answer

A)    
B)    
C)    
D)    
E) CH3I 
A)    
B)    
C)    
D)    
E) CH3I

Question 15

In each of the pairs below,which is the best nucleophile in alcoholic solvents?
a.CH3S- or CH3O-
b.(CH3)2NH or (CH3)3N
c.Cl- or F-
d.SCN- or OCN-

Accepted Answer

a.CH₃S^- ^b.(CH₃⁾₂NH c

Question 16

Which of the following alkyl halides gives the fastest SN1 reaction?

Accepted Answer

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

Question 17

Draw the product for the following SN2 reaction.

Accepted Answer

Question 18

Provide the major organic product(s)in the reaction below.

Accepted Answer

The answer of Provide the major organic product(s)in the reaction...

Question 19

The specific rotation of optically pure (R)-sec-butyl alcohol is -13.52°.An optically pure sample of (R)-sec-butyl bromide was converted into the corresponding sec-butyl alcohol via an SN2 reaction.What is the specific rotation of the product,assuming 100% yield?

Accepted Answer

A) -13.52° 
B) between 0° and -13.52° 
C) between 0° and +13.52° 
D) +13.52° 
E) zero 
A) -13.52° 
B) between 0° and -13.52° 
C) between 0° and +13.52° 
D) +13.52° 
E) zero

Question 20

Can primary alkyl halides react by SN2,SN1,E2,and E1 mechanisms? Are any of these mechanisms prohibited? What conditions favor a particular mechanism?

Accepted Answer

Only S_N2 and E2 pathways are available to

Exam 9: Substitution and Elimination Reactions of Alkyl Halides

Predict the mechanism of the reaction and the reagent needed to carry out the following transformation.

Why is the alkyl halide below not capable of undergoing an E2 reaction upon treatment with sodium ethoxide?

Which of the following halides is most reactive in an E2 reaction with sodium methoxide?

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

The hydrolysis of tert-butyl chloride proceeds more rapidly in a solvent mixture which is 70% water/30% acetone than in one which is 30% water/70% acetone.Why?

Provide the major organic product(s)in the reaction below.

Which of the following correctly reflects relative stabilities of carbocations?

What is/are the product(s)of the following reaction?

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

Draw the product of the following reaction.

Provide the structure of the major organic product which results when 2-bromo-2-methylbutane is treated with sodium ethoxide.

Name the products of the following SN2 reactions.

Give the major product for the following E1 reaction.

Which of the following alkyl halides undergoes E1 reactions with the fastest rate?

In each of the pairs below,which is the best nucleophile in alcoholic solvents? a.CH3S- or CH3O- b.(CH3)2NH or (CH3)3N c.Cl- or F- d.SCN- or OCN-

Which of the following alkyl halides gives the fastest SN1 reaction?

Draw the product for the following SN2 reaction.

Provide the major organic product(s)in the reaction below.

The specific rotation of optically pure (R)-sec-butyl alcohol is -13.52°.An optically pure sample of (R)-sec-butyl bromide was converted into the corresponding sec-butyl alcohol via an SN2 reaction.What is the specific rotation of the product,assuming 100% yield?

Can primary alkyl halides react by SN2,SN1,E2,and E1 mechanisms? Are any of these mechanisms prohibited? What conditions favor a particular mechanism?

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

Name the products of the following S_N2 reactions.

In each of the pairs below,which is the best nucleophile in alcoholic solvents? a.CH₃S^- or CH₃O^- ^b.(CH₃⁾₂NH or (CH₃⁾₃^N ^{c.Cl- or F-} ^{d.SCN- or OCN-}

Which of the following alkyl halides gives the fastest S_N1 reaction?

Draw the product for the following S_N2 reaction.

The specific rotation of optically pure (R)-sec-butyl alcohol is -13.52°.An optically pure sample of (R)-sec-butyl bromide was converted into the corresponding sec-butyl alcohol via an S_N2 reaction.What is the specific rotation of the product,assuming 100% yield?

Can primary alkyl halides react by S_N2,S_N1,E2,and E1 mechanisms? Are any of these mechanisms prohibited? What conditions favor a particular mechanism?