Chapter 15, Problem 15.7P

Complete these reactions involving lithium diorganocopper (Gilman) reagents.

1. (a)

1. (b)

1. (c)

1. (d)

Interpretation Introduction

Interpretation:

The necessary inorganic reagents have 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.

Gilman reagent: The lithium copper (diorganocopper) reagent compound $(R_{2}CuLi)$, 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 $(R_{2}CuLi)$ have a transition as their metal atom, they are used to form new carbon-carbon bonds.

• ✓  Organocuprate $(R_{2}CuLi)$ 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.

Explanation of Solution

The synthesis of product transformation is shown below.

The 1-bromocyclohexane (A) reacted with Gilman reagent (dimethyl cuprate), this reagent is attacking for $C-Br$ adjecent position to the bromine attached carbon atom followed by elimination of bromo group which yields the alkene (B).

Interpretation Introduction

Interpretation:

The necessary inorganic reagents have 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.

Gilman reagent: The lithium copper (diorganocopper) reagent compound $(R_{2}CuLi)$, 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 $(R_{2}CuLi)$ have a transition as their metal atom, they are used to form new carbon-carbon bonds.

• ✓  Organocuprate $(R_{2}CuLi)$ 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.

Explanation of Solution

The synthesis of product transformation is shown below.

The 1-bromo cyclohexane (A) treated with Gilman reagent in presence of ether which corresponding yields the butyl cyclohexene (B). The simple transformation reaction is shown above.

Interpretation Introduction

Interpretation:

The necessary inorganic reagents have 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.

Gilman reagent: The lithium copper (diorganocopper) reagent compound $(R_{2}CuLi)$, 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 $(R_{2}CuLi)$ have a transition as their metal atom, they are used to form new carbon-carbon bonds.

• ✓  Organocuprate $(R_{2}CuLi)$ 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.

Explanation of Solution

The synthesis of product transformation is shown below.

The 1-Iodobutane (A) is reacted with Gilman reagent in presence of ether which corresponding yields the 2,2’-dimethylhexane (B). The simple transformation reaction is shown above.

Interpretation Introduction

Interpretation:

The necessary inorganic reagents have 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.

Gilman reagent: The lithium copper (diorganocopper) reagent compound $(R_{2}CuLi)$, 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 $(R_{2}CuLi)$ have a transition as their metal atom, they are used to form new carbon-carbon bonds.

• ✓  Organocuprate $(R_{2}CuLi)$ 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.

Explanation of Solution

The synthesis of product transformation is shown below.

The alkene (A) is reacted with Gilman reagent in presence of ether which corresponding yields the product (B).