Essential Organic Chemistry (3rd Edition)
Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
Question
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Chapter 12, Problem 35P

(a)

Interpretation Introduction

Interpretation:

The product formed in the given reaction has to be shown with the stereochemistry.

Concept Introduction:

Grignard reagent: Alkyl, vinyl, or aryl-magnesium halides are called as Grignard reagents.

The chemical formula of the Grignard reagent is RMgX.

  WhereR-Alkyloraryl orvinylX-HalogenssuchasBr,ClorI

Grignard reaction with ketone:

Grignard regent reacts with ketone followed by acidic work up to form secondary or tertiary alcohol.

General scheme:

  Essential Organic Chemistry (3rd Edition), Chapter 12, Problem 35P , additional homework tip  1

Stereocenter: In the product of a chemical reaction, if a carbon atom has been attached with four different carbon atoms, then it is known as chiral carbon atom or stereocenter in the product. The bond of the functional group because of which a new chiral carbon is supposed to form has to be represented in solid wedge bond.

(b)

Interpretation Introduction

Interpretation:

The product formed in the given reaction has to be shown with the stereochemistry.

Concept Introduction:

 NaBH4 - Sodium borohydride is a reducing agent.

 It reduces aldehydes, ketones and carboxylic acids into alcohols.

 General scheme:

  Essential Organic Chemistry (3rd Edition), Chapter 12, Problem 35P , additional homework tip  2

Stereocenter: In the product of a chemical reaction, if a carbon atom has been attached with four different carbon atoms, then it is known as chiral carbon atom or stereocenter in the product. The bond of the functional group because of which a new chiral carbon is supposed to form has to be represented in solid wedge bond.

(c)

Interpretation Introduction

Interpretation:

The product formed in the given reaction has to be shown with the stereochemistry.

Concept Introduction:

Imine formation:

Aldehyde or ketone reacts with a primary amine and forms imine in mildly acidic conditions.

Example for the formation of imine is shown here:

  Essential Organic Chemistry (3rd Edition), Chapter 12, Problem 35P , additional homework tip  3

  • Imines contain C=N .
  • Imines are also called as Schiff bases, named after Hugo Schiff who described their formation.

Stereocenter: In the product of a chemical reaction, if a carbon atom has been attached with four different carbon atoms, then it is known as chiral carbon atom or stereocenter in the product. The bond of the functional group because of which a new chiral carbon is supposed to form has to be represented in solid wedge bond.

(d)

Interpretation Introduction

Interpretation:

The product formed in the given reaction has to be shown with the stereochemistry.

Concept Introduction:

 LiAlH4 - Lithium aluminium hydride is a reducing agent.

It reduces aldehydes, ketones and esters into alcohol.

Conversion of ester into alcohol:

  Essential Organic Chemistry (3rd Edition), Chapter 12, Problem 35P , additional homework tip  4

Stereocenter: In the product of a chemical reaction, if a carbon atom has been attached with four different carbon atoms, then it is known as chiral carbon atom or stereocenter in the product. The bond of the functional group because of which a new chiral carbon is supposed to form has to be represented in solid wedge bond.

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