The major product has to be identified. Concept introduction: S N 1 reaction: The reaction of alcohols with acids like hydrochloric acid or hydrobromic which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product. Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation. Primary alcohol is less stable therefore it won’t undergoes S N 1 substitution reaction.

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Answer 1

Question

Chapter 9, Problem 31P

(a)

Interpretation Introduction

Interpretation:

The major product has to be identified.

Concept introduction:

S_N1 reaction:

The reaction of alcohols with acids like hydrochloric acid or hydrobromic which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergoes S_N1 substitution reaction.

(b)

Interpretation Introduction

Interpretation:

The major product has to be identified.

Concept introduction:

S_N2 reaction:

The alcohols are reaction with acids like hydrochloric acid or hydrobromic which yield the corresponding substitution product. Primary alcohol undergoes S_N2 substitution reaction than secondary alcohol than tertiary alcohol because S_N2 reaction is simultaneous reaction.

(c)

Interpretation Introduction

Interpretation:

The major product has to be identified.

Concept introduction:

Dehydration reaction:

Removal of water molecule from the reaction, the alcohol is treated with strong acid like sulfuric acid.

The stability of carbocation is given below,

Tertiary carbocation is more stable than the secondary and primary.

(d)

Interpretation Introduction

Interpretation:

The major product should be identified.

Concept introduction:

S_N1 reaction:

The alcohols is reaction with acids like hydrochloric acid or hydrobromic which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergoes S_N1 substitution reaction.

(e)

Interpretation Introduction

Interpretation:

The major product should be identified.

Concept introduction:

In the presence of acid catalyst, this reaction takes place through partial S_N1 and partial S_N2 pathway. Epoxides are reactive, Epoxides get protonated followed by alcohol attacks to the stable carbocation and form the product.

Epoxides are reactive, methoxide ion attacks the Epoxides in a less sterically hindered position which forms the alkoxide ion, and then it gets proton from alcohol which form the product.

(f)

Interpretation Introduction

Interpretation:

The major product should be identified.

Concept introduction:

In the presence of acid catalyst, this reaction takes place through partial S_N1 and partial S_N2 pathway. It is not a pure S_N1 reaction because a carbocation is not formed fully and not a pure S_N2 reaction because the leaving group begins to depart before the compound is attacked by the nucleophile. Epoxides are reactive; Epoxides get protonated followed by alcohol attacks to the stable carbocation and form the product.

Epoxides are reactive, methoxide ion attacks the Epoxides in a less sterically hindered position which forms the alkoxide ion, and then it gets proton from alcohol which form the product. When a nucleophile attacks an unprotonated epoxide, the reaction is a pure S_N2 reaction.

Note: Under acidic conditions, the nucleophile preferentially attacks the more substuituted ring carbon. Under Basic conditions, the nucleophile preferentially attacks the less substuituted ring carbon.

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You are trying to decide if there is a single reagent you can add that will make the following synthesis possible without any other major side products: xi 1. ☑ 2. H₂O хе i Draw the missing reagent X you think will make this synthesis work in the drawing area below. If there is no reagent that will make your desired product in good yield or without complications, just check the box under the drawing area and leave it blank. Click and drag to start drawing a structure. There is no reagent that will make this synthesis work without complications. : ☐ S ☐

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For each reaction below, decide if the first stable organic product that forms in solution will create a new C-C bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. NH2 CI MgCl ? Will the first product that forms in this reaction create a new CC bond? Yes No MgBr ? Will the first product that forms in this reaction create a new CC bond? Yes No G टे

Answer 2

Question

Chapter 9, Problem 31P

(a)

Interpretation Introduction

Interpretation:

The major product has to be identified.

Concept introduction:

S_N1 reaction:

The reaction of alcohols with acids like hydrochloric acid or hydrobromic which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergoes S_N1 substitution reaction.

(b)

Interpretation Introduction

Interpretation:

The major product has to be identified.

Concept introduction:

S_N2 reaction:

The alcohols are reaction with acids like hydrochloric acid or hydrobromic which yield the corresponding substitution product. Primary alcohol undergoes S_N2 substitution reaction than secondary alcohol than tertiary alcohol because S_N2 reaction is simultaneous reaction.

(c)

Interpretation Introduction

Interpretation:

The major product has to be identified.

Concept introduction:

Dehydration reaction:

Removal of water molecule from the reaction, the alcohol is treated with strong acid like sulfuric acid.

The stability of carbocation is given below,

Tertiary carbocation is more stable than the secondary and primary.

(d)

Interpretation Introduction

Interpretation:

The major product should be identified.

Concept introduction:

S_N1 reaction:

The alcohols is reaction with acids like hydrochloric acid or hydrobromic which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergoes S_N1 substitution reaction.

(e)

Interpretation Introduction

Interpretation:

The major product should be identified.

Concept introduction:

In the presence of acid catalyst, this reaction takes place through partial S_N1 and partial S_N2 pathway. Epoxides are reactive, Epoxides get protonated followed by alcohol attacks to the stable carbocation and form the product.

Epoxides are reactive, methoxide ion attacks the Epoxides in a less sterically hindered position which forms the alkoxide ion, and then it gets proton from alcohol which form the product.

(f)

Interpretation Introduction

Interpretation:

The major product should be identified.

Concept introduction:

In the presence of acid catalyst, this reaction takes place through partial S_N1 and partial S_N2 pathway. It is not a pure S_N1 reaction because a carbocation is not formed fully and not a pure S_N2 reaction because the leaving group begins to depart before the compound is attacked by the nucleophile. Epoxides are reactive; Epoxides get protonated followed by alcohol attacks to the stable carbocation and form the product.

Epoxides are reactive, methoxide ion attacks the Epoxides in a less sterically hindered position which forms the alkoxide ion, and then it gets proton from alcohol which form the product. When a nucleophile attacks an unprotonated epoxide, the reaction is a pure S_N2 reaction.

Note: Under acidic conditions, the nucleophile preferentially attacks the more substuituted ring carbon. Under Basic conditions, the nucleophile preferentially attacks the less substuituted ring carbon.

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Answer 3

Question

Chapter 9, Problem 31P

(a)

Interpretation Introduction

Interpretation:

The major product has to be identified.

Concept introduction:

S_N1 reaction:

The reaction of alcohols with acids like hydrochloric acid or hydrobromic which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergoes S_N1 substitution reaction.

(b)

Interpretation Introduction

Interpretation:

The major product has to be identified.

Concept introduction:

S_N2 reaction:

The alcohols are reaction with acids like hydrochloric acid or hydrobromic which yield the corresponding substitution product. Primary alcohol undergoes S_N2 substitution reaction than secondary alcohol than tertiary alcohol because S_N2 reaction is simultaneous reaction.

(c)

Interpretation Introduction

Interpretation:

The major product has to be identified.

Concept introduction:

Dehydration reaction:

Removal of water molecule from the reaction, the alcohol is treated with strong acid like sulfuric acid.

The stability of carbocation is given below,

Tertiary carbocation is more stable than the secondary and primary.

(d)

Interpretation Introduction

Interpretation:

The major product should be identified.

Concept introduction:

S_N1 reaction:

The alcohols is reaction with acids like hydrochloric acid or hydrobromic which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergoes S_N1 substitution reaction.

(e)

Interpretation Introduction

Interpretation:

The major product should be identified.

Concept introduction:

In the presence of acid catalyst, this reaction takes place through partial S_N1 and partial S_N2 pathway. Epoxides are reactive, Epoxides get protonated followed by alcohol attacks to the stable carbocation and form the product.

Epoxides are reactive, methoxide ion attacks the Epoxides in a less sterically hindered position which forms the alkoxide ion, and then it gets proton from alcohol which form the product.

(f)

Interpretation Introduction

Interpretation:

The major product should be identified.

Concept introduction:

In the presence of acid catalyst, this reaction takes place through partial S_N1 and partial S_N2 pathway. It is not a pure S_N1 reaction because a carbocation is not formed fully and not a pure S_N2 reaction because the leaving group begins to depart before the compound is attacked by the nucleophile. Epoxides are reactive; Epoxides get protonated followed by alcohol attacks to the stable carbocation and form the product.

Epoxides are reactive, methoxide ion attacks the Epoxides in a less sterically hindered position which forms the alkoxide ion, and then it gets proton from alcohol which form the product. When a nucleophile attacks an unprotonated epoxide, the reaction is a pure S_N2 reaction.

Note: Under acidic conditions, the nucleophile preferentially attacks the more substuituted ring carbon. Under Basic conditions, the nucleophile preferentially attacks the less substuituted ring carbon.

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Answer 4

Question

Chapter 9, Problem 31P

(a)

Interpretation Introduction

Interpretation:

The major product has to be identified.

Concept introduction:

S_N1 reaction:

The reaction of alcohols with acids like hydrochloric acid or hydrobromic which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergoes S_N1 substitution reaction.

(b)

Interpretation Introduction

Interpretation:

The major product has to be identified.

Concept introduction:

S_N2 reaction:

The alcohols are reaction with acids like hydrochloric acid or hydrobromic which yield the corresponding substitution product. Primary alcohol undergoes S_N2 substitution reaction than secondary alcohol than tertiary alcohol because S_N2 reaction is simultaneous reaction.

(c)

Interpretation Introduction

Interpretation:

The major product has to be identified.

Concept introduction:

Dehydration reaction:

Removal of water molecule from the reaction, the alcohol is treated with strong acid like sulfuric acid.

The stability of carbocation is given below,

Tertiary carbocation is more stable than the secondary and primary.

(d)

Interpretation Introduction

Interpretation:

The major product should be identified.

Concept introduction:

S_N1 reaction:

The alcohols is reaction with acids like hydrochloric acid or hydrobromic which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergoes S_N1 substitution reaction.

(e)

Interpretation Introduction

Interpretation:

The major product should be identified.

Concept introduction:

In the presence of acid catalyst, this reaction takes place through partial S_N1 and partial S_N2 pathway. Epoxides are reactive, Epoxides get protonated followed by alcohol attacks to the stable carbocation and form the product.

Epoxides are reactive, methoxide ion attacks the Epoxides in a less sterically hindered position which forms the alkoxide ion, and then it gets proton from alcohol which form the product.

(f)

Interpretation Introduction

Interpretation:

The major product should be identified.

Concept introduction:

In the presence of acid catalyst, this reaction takes place through partial S_N1 and partial S_N2 pathway. It is not a pure S_N1 reaction because a carbocation is not formed fully and not a pure S_N2 reaction because the leaving group begins to depart before the compound is attacked by the nucleophile. Epoxides are reactive; Epoxides get protonated followed by alcohol attacks to the stable carbocation and form the product.

Epoxides are reactive, methoxide ion attacks the Epoxides in a less sterically hindered position which forms the alkoxide ion, and then it gets proton from alcohol which form the product. When a nucleophile attacks an unprotonated epoxide, the reaction is a pure S_N2 reaction.

Note: Under acidic conditions, the nucleophile preferentially attacks the more substuituted ring carbon. Under Basic conditions, the nucleophile preferentially attacks the less substuituted ring carbon.

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Answer 5

Chapter 9, Problem 31P

(a)

Interpretation Introduction

Interpretation:

The major product has to be identified.

Concept introduction:

S_N1 reaction:

The reaction of alcohols with acids like hydrochloric acid or hydrobromic which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergoes S_N1 substitution reaction.

(b)

Interpretation Introduction

Interpretation:

The major product has to be identified.

Concept introduction:

S_N2 reaction:

The alcohols are reaction with acids like hydrochloric acid or hydrobromic which yield the corresponding substitution product. Primary alcohol undergoes S_N2 substitution reaction than secondary alcohol than tertiary alcohol because S_N2 reaction is simultaneous reaction.

(c)

Interpretation Introduction

Interpretation:

The major product has to be identified.

Concept introduction:

Dehydration reaction:

Removal of water molecule from the reaction, the alcohol is treated with strong acid like sulfuric acid.

The stability of carbocation is given below,

Tertiary carbocation is more stable than the secondary and primary.

(d)

Interpretation Introduction

Interpretation:

The major product should be identified.

Concept introduction:

S_N1 reaction:

The alcohols is reaction with acids like hydrochloric acid or hydrobromic which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergoes S_N1 substitution reaction.

(e)

Interpretation Introduction

Interpretation:

The major product should be identified.

Concept introduction:

In the presence of acid catalyst, this reaction takes place through partial S_N1 and partial S_N2 pathway. Epoxides are reactive, Epoxides get protonated followed by alcohol attacks to the stable carbocation and form the product.

Epoxides are reactive, methoxide ion attacks the Epoxides in a less sterically hindered position which forms the alkoxide ion, and then it gets proton from alcohol which form the product.

(f)

Interpretation Introduction

Interpretation:

The major product should be identified.

Concept introduction:

In the presence of acid catalyst, this reaction takes place through partial S_N1 and partial S_N2 pathway. It is not a pure S_N1 reaction because a carbocation is not formed fully and not a pure S_N2 reaction because the leaving group begins to depart before the compound is attacked by the nucleophile. Epoxides are reactive; Epoxides get protonated followed by alcohol attacks to the stable carbocation and form the product.

Epoxides are reactive, methoxide ion attacks the Epoxides in a less sterically hindered position which forms the alkoxide ion, and then it gets proton from alcohol which form the product. When a nucleophile attacks an unprotonated epoxide, the reaction is a pure S_N2 reaction.

Note: Under acidic conditions, the nucleophile preferentially attacks the more substuituted ring carbon. Under Basic conditions, the nucleophile preferentially attacks the less substuituted ring carbon.

Answer 6

Chapter 9, Problem 31P

(a)

Interpretation Introduction

Interpretation:

The major product has to be identified.

Concept introduction:

S_N1 reaction:

The reaction of alcohols with acids like hydrochloric acid or hydrobromic which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergoes S_N1 substitution reaction.

Answer 7

Chapter 9, Problem 31P

(a)

Interpretation Introduction

Interpretation:

The major product has to be identified.

Concept introduction:

S_N1 reaction:

The reaction of alcohols with acids like hydrochloric acid or hydrobromic which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergoes S_N1 substitution reaction.

Answer 8

(b)

Interpretation Introduction

Interpretation:

The major product has to be identified.

Concept introduction:

S_N2 reaction:

The alcohols are reaction with acids like hydrochloric acid or hydrobromic which yield the corresponding substitution product. Primary alcohol undergoes S_N2 substitution reaction than secondary alcohol than tertiary alcohol because S_N2 reaction is simultaneous reaction.

Answer 9

(b)

Interpretation Introduction

Interpretation:

The major product has to be identified.

Concept introduction:

S_N2 reaction:

The alcohols are reaction with acids like hydrochloric acid or hydrobromic which yield the corresponding substitution product. Primary alcohol undergoes S_N2 substitution reaction than secondary alcohol than tertiary alcohol because S_N2 reaction is simultaneous reaction.

Answer 10

(c)

Interpretation Introduction

Interpretation:

The major product has to be identified.

Concept introduction:

Dehydration reaction:

Removal of water molecule from the reaction, the alcohol is treated with strong acid like sulfuric acid.

The stability of carbocation is given below,

Tertiary carbocation is more stable than the secondary and primary.

Answer 11

(c)

Interpretation Introduction

Interpretation:

The major product has to be identified.

Concept introduction:

Dehydration reaction:

Removal of water molecule from the reaction, the alcohol is treated with strong acid like sulfuric acid.

The stability of carbocation is given below,

Tertiary carbocation is more stable than the secondary and primary.

Answer 12

(d)

Interpretation Introduction

Interpretation:

The major product should be identified.

Concept introduction:

S_N1 reaction:

The alcohols is reaction with acids like hydrochloric acid or hydrobromic which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergoes S_N1 substitution reaction.

Answer 13

(d)

Interpretation Introduction

Interpretation:

The major product should be identified.

Concept introduction:

S_N1 reaction:

The alcohols is reaction with acids like hydrochloric acid or hydrobromic which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergoes S_N1 substitution reaction.

Answer 14

(e)

Interpretation Introduction

Interpretation:

The major product should be identified.

Concept introduction:

In the presence of acid catalyst, this reaction takes place through partial S_N1 and partial S_N2 pathway. Epoxides are reactive, Epoxides get protonated followed by alcohol attacks to the stable carbocation and form the product.

Epoxides are reactive, methoxide ion attacks the Epoxides in a less sterically hindered position which forms the alkoxide ion, and then it gets proton from alcohol which form the product.

Answer 15

(e)

Interpretation Introduction

Interpretation:

The major product should be identified.

Concept introduction:

In the presence of acid catalyst, this reaction takes place through partial S_N1 and partial S_N2 pathway. Epoxides are reactive, Epoxides get protonated followed by alcohol attacks to the stable carbocation and form the product.

Epoxides are reactive, methoxide ion attacks the Epoxides in a less sterically hindered position which forms the alkoxide ion, and then it gets proton from alcohol which form the product.

Answer 16

(f)

Interpretation Introduction

Interpretation:

The major product should be identified.

Concept introduction:

In the presence of acid catalyst, this reaction takes place through partial S_N1 and partial S_N2 pathway. It is not a pure S_N1 reaction because a carbocation is not formed fully and not a pure S_N2 reaction because the leaving group begins to depart before the compound is attacked by the nucleophile. Epoxides are reactive; Epoxides get protonated followed by alcohol attacks to the stable carbocation and form the product.

Epoxides are reactive, methoxide ion attacks the Epoxides in a less sterically hindered position which forms the alkoxide ion, and then it gets proton from alcohol which form the product. When a nucleophile attacks an unprotonated epoxide, the reaction is a pure S_N2 reaction.

Note: Under acidic conditions, the nucleophile preferentially attacks the more substuituted ring carbon. Under Basic conditions, the nucleophile preferentially attacks the less substuituted ring carbon.

Answer 17

(f)

Interpretation Introduction

Interpretation:

The major product should be identified.

Concept introduction:

In the presence of acid catalyst, this reaction takes place through partial S_N1 and partial S_N2 pathway. It is not a pure S_N1 reaction because a carbocation is not formed fully and not a pure S_N2 reaction because the leaving group begins to depart before the compound is attacked by the nucleophile. Epoxides are reactive; Epoxides get protonated followed by alcohol attacks to the stable carbocation and form the product.

Epoxides are reactive, methoxide ion attacks the Epoxides in a less sterically hindered position which forms the alkoxide ion, and then it gets proton from alcohol which form the product. When a nucleophile attacks an unprotonated epoxide, the reaction is a pure S_N2 reaction.

Note: Under acidic conditions, the nucleophile preferentially attacks the more substuituted ring carbon. Under Basic conditions, the nucleophile preferentially attacks the less substuituted ring carbon.

Answer 18

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Answer 19

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Answer 20

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Answer 21

Ch. 9.1 - Draw the structures of straight-chain alcohols...Ch. 9.1 - Prob. 2P Ch. 9.1 - Prob. 3P Ch. 9.2 - Why are NH3 and CH3NH2 no longer nucleophiles when...Ch. 9.2 - Prob. 5P Ch. 9.2 - The observed relative reactivities of primary,...Ch. 9.4 - Which of the following alcohols would dehydrate...Ch. 9.4 - Prob. 10P Ch. 9.4 - Prob. 11P Ch. 9.4 - Prob. 12P

Solution Summary: The author explains the mechanism of the S N 1 reaction and the tertiary carbocation reaction.

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Chapter 9 Solutions