Organic Chemistry & Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition)
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Chapter 10, Problem 35P

Draw the major product obtained when each of the following alkyl halides undergoes an E2 reaction:

Chapter 10, Problem 35P, Draw the major product obtained when each of the following alkyl halides undergoes an E2 reaction: , example  1

Chapter 10, Problem 35P, Draw the major product obtained when each of the following alkyl halides undergoes an E2 reaction: , example  2

Chapter 10, Problem 35P, Draw the major product obtained when each of the following alkyl halides undergoes an E2 reaction: , example  3

Chapter 10, Problem 35P, Draw the major product obtained when each of the following alkyl halides undergoes an E2 reaction: , example  4

Chapter 10, Problem 35P, Draw the major product obtained when each of the following alkyl halides undergoes an E2 reaction: , example  5

Chapter 10, Problem 35P, Draw the major product obtained when each of the following alkyl halides undergoes an E2 reaction: , example  6

(a)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Major product formed when given alkyl halides undergoes E2 reaction has to be drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.  A strong base favours an E2 reaction.  A high concentration of a base favours an E2 reaction.  If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant.  If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.  The major product is a stable alkene, unless the reactants are sterically hindered.

Explanation of Solution

The product when given compound undergo E2 addition,

Organic Chemistry & Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 10, Problem 35P , additional homework tip  1

For an E2 reaction major product is the more stable alkene.  The reactant is a secondary alkyl halide, undergo E2 reactions.

(b)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Major product formed when given alkyl halides undergoes E2 reaction is to be identified.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

Explanation of Solution

Organic Chemistry & Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 10, Problem 35P , additional homework tip  2

Chlorocyclohexane is a less stable conformer undergo E2 reaction as Cl is in the axial position and thus makes the reaction slower.

The reactant is a secondary alkyl halide, undergo E2 reactions.

(c)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Major product formed when given alkyl halides undergoes E2 reaction is to be identified.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.  A strong base favours an E2 reaction.  A high concentration of a base favours an E2 reaction.  If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant.  If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.  The major product is a stable alkene, unless the reactants are sterically hindered.

Explanation of Solution

Product of given compound when undergo E2 reaction,

Organic Chemistry & Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 10, Problem 35P , additional homework tip  3

More substituted alkene is more stable therefore should be the major product.

(d)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Major product formed when given alkyl halides undergoes E2 reaction is to be identified.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.  A strong base favours an E2 reaction.  A high concentration of a base favours an E2 reaction.  If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant.  If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

The major product is a stable alkene, unless the reactants are sterically hindered.

Explanation of Solution

Product of given compound when undergo E2 reaction,

Organic Chemistry & Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 10, Problem 35P , additional homework tip  4

Chloromethyl cyclohexane on E2 reaction gives methylene cyclohexane.  And E2 reaction is regioselective: major product is the more substituted stable alkene.

(e)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Major product formed when given alkyl halides undergoes E2 reaction is to be identified.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.  A strong base favours an E2 reaction.  A high concentration of a base favours an E2 reaction.  If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant.  If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

The major product is a stable alkene, unless the reactants are sterically hindered.

Explanation of Solution

Product of given compound when undergo E2 reaction,

Organic Chemistry & Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 10, Problem 35P , additional homework tip  5

The reactant is a secondary alkyl halide, undergo E2 reactions.

(f)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Major product formed when given alkyl halides undergoes E2 reaction is to be identified.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.  A strong base favours an E2 reaction.  A high concentration of a base favours an E2 reaction.  If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant.  If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

The major product is a stable alkene, unless the reactants are sterically hindered.

Explanation of Solution

Product of given compound when undergo E2 reaction,

Organic Chemistry & Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 10, Problem 35P , additional homework tip  6

An E2 reaction is regioselective: major product is the more substituted stable alkene.

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Chapter 10 Solutions

Organic Chemistry & Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition)

Ch. 10.4 - Prob. 11PCh. 10.5 - Prob. 12PCh. 10.6 - Prob. 14PCh. 10.7 - Why do cis-1-bromo-2-ethylcyclohexane and...Ch. 10.7 - Which isomer reacts more rapidly in an E2...Ch. 10.7 - Prob. 18PCh. 10.8 - Prob. 19PCh. 10.8 - Prob. 20PCh. 10.9 - Prob. 21PCh. 10.9 - Explain why only a substitution product and no...Ch. 10.9 - Prob. 23PCh. 10.9 - Prob. 24PCh. 10.9 - Prob. 25PCh. 10.9 - a. Explain why 1-bromo-2,2-dimethylpropane has...Ch. 10.10 - A small amount of another organic product is...Ch. 10.10 - What is the best way to prepare the following...Ch. 10.10 - Prob. 29PCh. 10.10 - Prob. 30PCh. 10.10 - Why is a cumulated diene not formed in the...Ch. 10.10 - What product is obtained when the following...Ch. 10.11 - Prob. 33PCh. 10.11 - Prob. 34PCh. 10 - Draw the major product obtained when each of the...Ch. 10 - Prob. 36PCh. 10 - a. Indicate how each of the following factors...Ch. 10 - Prob. 38PCh. 10 - A chemist wanted to synthesize the...Ch. 10 - Prob. 40PCh. 10 - Prob. 41PCh. 10 - Prob. 42PCh. 10 - Starting with an alkyl halide, how could the...Ch. 10 - Indicate which species in each pair gives a higher...Ch. 10 - Prob. 45PCh. 10 - For each of the following alkyl halides, indicate...Ch. 10 - Prob. 47PCh. 10 - When 2-bromo-2,3-dimethylbutane reacts with a...Ch. 10 - Prob. 49PCh. 10 - When the following compound undergoes solvolysis...Ch. 10 - cis-1-Bromo-4-tert-butylcyclohexane and...Ch. 10 - Draw the substitution and elimination products.Ch. 10 - Prob. 53PCh. 10 - Prob. 54PCh. 10 - Which of the following hexachlorocyclohexanes is...Ch. 10 - Explain why the rate of the reaction of...Ch. 10 - Prob. 57PCh. 10 - Two elimination products are obtained from the...Ch. 10 - Draw the structures or the product of the obtained...Ch. 10 - How could you prepare the following compounds from...Ch. 10 - cis-4-Bromocyclohexanol and...Ch. 10 - Prob. 62PCh. 10 - Prob. 63P
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