Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 5, Problem 5.31AP
Interpretation Introduction

(a)

Interpretation:

The missing reactant or product for the given equation is to be stated.

Concept introduction:

In oxidative cleavage both the sigma and pi bond of the alkene is broken and two carbonyl compounds are formed. When ozone is added to the alkene, unstable intermediate molozonide is formed which rearranges to ozonide. This ozonide is reduced to form two carbonyl compounds in presence of CH3SCH3.

Interpretation Introduction

(b)

Interpretation:

The missing reactant or product for the given equation is to be stated.

Concept introduction:

In the presence of ozone and CH3SCH3, oxidative cleavage occurs. In oxidative cleavage both the sigma and pi bond of the alkene is broken and two carbonyl compounds are formed. When ozone is added to the alkene, unstable intermediate molozonide is formed which rearranges to ozonide. This ozonide is reduced to form two carbonyl compounds in presence of CH3SCH3.

Interpretation Introduction

(c)

Interpretation:

The missing reactant or product for the given equation is to be stated.

Concept introduction:

The reaction of hydrogen halide with alkene results in the formation of alkyl halide. This type of reaction is an electrophilic addition of hydrogen halide. Electrophilic addition reactions are those in which breaking of pi bond take place to form new sigma bond.

Interpretation Introduction

(d)

Interpretation:

The missing reactant or product for the given equation is to be stated.

Concept introduction:

The reaction of hydrogen halide with alkene results in the formation of alkyl halide. This type of reaction is an electrophilic addition of hydrogen halide. Electrophilic addition reactions are those in which breaking of pi bond take place to form new sigma bond.

Interpretation Introduction

(e)

Interpretation:

The missing reactant or product for the given equation is to be stated.

Concept introduction:

Hydroboration reaction is a two step reaction, which involves conversion of alkene into alcohol. This type of reaction follows anti-Markovnikov rule.

Anti markovinkov rule states that the positive part of acid attached to that carbon atom in C=C bond which carries minimum number of hydrogen atoms and the negative part of acid will attach to that carbon atom in C=C bond which has maximum number of hydrogen atoms.

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Write the product or products that will be formed as a result of the reactions given in each line below.
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1) The carbon-oxygen double bond present in aldehydes and ketones is very polar. What does this mean and how does it arise? 2) The carbon-oxygen double bond is readily attacked by nucleophiles like cyanide ions or ammonia.           (i) What do you understand by the term nucleophile?           (ii) Which part of the carbon-oxygen double bond is attractive to nucleophiles? 3) Why is there a difference between aldehydes and ketones in their response to oxidizing agents such as potassium dichromate(VI) solution acidified with dilute sulfuric acid?
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