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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2. Name the following hydrocarbons. (9 marks) a) HHHHHHHH H-C-C- H-O-S b) HCEC-CH3 H H H H H d) c) H C=C- H H H e) CH3 CH3 CH2CH=CH-CH=CHCH3 HHHH H-C-C-C-C-H H HH H f) large CH2CH3 pola H3C section lovels tower, able ocart firs g) Tower H3C-CH2 then in H3C-CH-CH-CH3 enblbano bne noitsidab Copyright © 2008. Durham Continuing Education CH3

Name the molecules & Identify any chiral center CH3CH2CH2CHCH₂CH₂CH₂CH₂ OH CH₂CHCH2CH3 Br CH3 CH3CHCH2CHCH2CH3 CH3

Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electrons-pushing arrows for the following reaction or mechanistic step(s).

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