Chapter 15, Problem 15.10P

Show how to prepare each compound from the given starting compound through the use of a lithium diorganocopper (Gilman) reagent.

1. (a) 4-Methylcyclopentene from 4-bromocyclopentene
2. (b) (Z)-2-Undecene from (Z)-1-bromopropene
3. (c) 1-Butylcyclohexene from 1-iodocyclohexene
4. (d) 1-Decene from 1-iodooctane
5. (e) 1,8-Nonadiene from 1,5-dibromopentane

Interpretation Introduction

Interpretation:

How to prepare the given target compound from the given starting compound thorough the use of Gilman reagent has to be shown.

Concept Introduction:

Addition and elimination Reaction:

• It is a type of reaction in which two reactants adding together to form a single product.
• It can be said as a reverse reaction of elimination reaction.
• It is a characteristic reaction of alkane.

Hydrogenation reaction is an addition reaction in which addition of hydrogen to an unsaturated molecule occurs

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 4-bromocyclopentene (A) is reacted with appropriate reagent in presence of ether conditions which corresponding yields the 4-methylcyclopentene (B). In this reaction addition and elimination process was occurred and completed equation and structural formula is shown above.

Interpretation Introduction

Interpretation:

How to prepare the given target compound from the given starting compound thorough the use of Gilman reagent has to be shown.

Concept Introduction:

Addition and elimination Reaction:

• It is a type of reaction in which two reactants adding together to form a single product.
• It can be said as a reverse reaction of elimination reaction.
• It is a characteristic reaction of alkane.

Hydrogenation reaction is an addition reaction in which addition of hydrogen to an unsaturated molecule occurs

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 (Z)-1-bromopropane (A) is reacted with lithium diorganocopper reagent in presence of ether conditions which corresponding yields the (Z)-2-Undecane (B). In this reaction addition and elimination process was occurred.

Interpretation Introduction

Interpretation:

How to prepare the given target compound from the given starting compound thorough the use of Gilman reagent has to be shown.

Concept Introduction:

Addition and elimination Reaction:

• It is a type of reaction in which two reactants adding together to form a single product.
• It can be said as a reverse reaction of elimination reaction.
• It is a characteristic reaction of alkane.

Hydrogenation reaction is an addition reaction in which addition of hydrogen to an unsaturated molecule occurs

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-Iodocyclohexene (A) is reacted with lithium diorganocopper reagent in presence of ether conditions which corresponding yields the 1-butylcyclohexene (B). The corresponding transformation reaction is placed above.

Interpretation Introduction

Interpretation:

How to prepare the given target compound from the given starting compound thorough the use of Gilman reagent has to be shown.

Concept Introduction:

Addition and elimination Reaction:

• It is a type of reaction in which two reactants adding together to form a single product.
• It can be said as a reverse reaction of elimination reaction.
• It is a characteristic reaction of alkane.

Hydrogenation reaction is an addition reaction in which addition of hydrogen to an unsaturated molecule occurs

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-Iodooctane (A) is reacted with lithium diorganocopper reagent in presence of ether conditions which corresponding yields the 1-Decene (B). The corresponding transformation reaction is placed above.

Interpretation Introduction

Interpretation:

How to prepare the given target compound from the given starting compound thorough the use of Gilman reagent has to be shown.

Concept Introduction:

Addition and elimination Reaction:

• It is a type of reaction in which two reactants adding together to form a single product.
• It can be said as a reverse reaction of elimination reaction.
• It is a characteristic reaction of alkane.

Hydrogenation reaction is an addition reaction in which addition of hydrogen to an unsaturated molecule occurs

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 1,5-dibromopentene (A) is reacted with corresponding lithium diorganocopper reagent in presence of ether conditions which corresponding yields the 1,8-Nanadiene (B). The corresponding transformation reaction is placed above.