Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 12, Problem 26P

(a)

Interpretation Introduction

Interpretation:

The necessary inorganic reagents has to be identified for the conversion of the given starting material to the respective product.

Concept Introduction:

Gilman reagent: The lithium copper (diorganocopper) reagent compound (R2CuLi), these reagent are very useful because unlike Grignard reagent and organolithium reagents, they react with organic halides to replace the halide group. With an alkyl (R) group.

Organometallic reagents such as organocuprate (R2CuLi) have a transition as their metal atom, they are used to form new carbon-carbon bonds.

  • Organocuprate (R2CuLi) are also known as Gilman Reagent.
  • It is prepared from an organolithium compound by reaction with cuprous iodide in diethyl ether or THF as follows.

Organic Chemistry, Chapter 12, Problem 26P , additional homework tip  1

(b)

Interpretation Introduction

Interpretation:

The necessary inorganic reagents has to be identified for the conversion of the given starting material to the respective product.

Concept Introduction:

Organocopper compounds: The Organocopper reagents react with alkyl, alkenyl and aryl halides to give alkylated product.

It is more selective and can be acetylated with acid chlorides without concomitant attack on ketons, alkyl halides and esters.

Reactivity RCOCl>RCHO>tosylatesiodides>expoxies>bromides>ketones>esters>nitrils

In the reaction with α,β-unsaturated carbonyl compounds, the Organocopper reagents prefer 1,4-addition over 1,3-addition.

(c)

Interpretation Introduction

Interpretation:

The necessary inorganic reagents has to be identified for the conversion of the given starting material to the respective product.

Concept Introduction:

Soda amide: It is used for deprotonation of week acids and also for elimination reaction, the amine anion (NH2) is the conjugate base of ammonia. This reagent good strong base it will deprotonate alkynes, alcohols and other functional groups in acidic protons such as as esters and ketones, it is very good nucleophile.

(d)

Interpretation Introduction

Interpretation:

The necessary inorganic reagents has to be identified for the conversion of the given starting material to the respective product.

Concept introduction:

Heck reaction: This reaction couples a vinylic or an aryl halide with an alkene in the presence of a base and a palladium catalyst PdL2, like as Suzuki reaction, the Heck reaction is a substitution reaction the alkyl group of the halide replace  a vinylic hydrogen of an alkene.

(e)

Interpretation Introduction

Interpretation:

The necessary inorganic reagents has to be identified for the conversion of the given starting material to the respective product.

Concept Introduction:

Organocopper compounds: The Organocopper reagents react with alkyl, alkenyl and aryl halides to give alkylated product.

It is more selective and can be acetylated with acid chlorides without concomitant attack on ketons, alkyl halides and esters.

Reactivity RCOCl>RCHO>tosylatesiodides>expoxies>bromides>ketones>esters>nitrils

In the reaction with α,β-unsaturated carbonyl compounds, the Organocopper reagents prefer 1,4-addition over 1,3-addition.

(f)

Interpretation Introduction

Interpretation:

The target molecules should be drawn for the given staring molecule by using specific reagent and its structure.

Concept Introduction:

Gilman reagent: The lithium copper (diorganocopper) reagent compound (R2CuLi), these reagent are very useful because unlike Grignard reagent and organolithium reagents, they react with organic halides to replace the halide group with an alkyl (R) group.

Organometallic reagents such as organocuprate (R2CuLi) have a transition as their metal atom, they are used to form new carbon-carbon bonds.

  • Organocuprate (R2CuLi) are also known as Gilman Reagent.
  • It is prepared from an organolithium compound by reaction with cuprous iodide in diethyl ether or THF as follows.

Organic Chemistry, Chapter 12, Problem 26P , additional homework tip  2

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