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Chapter 6: Problem 117

Describe dehalogenation of vicinal dihalides to obtain an alkene.

Short Answer

Expert verified
Dehalogenation of vicinal dihalides involves converting a compound with two halogen atoms on adjacent carbon atoms into an alkene by removing the halogen atoms and forming a double bond between the carbons. This process typically uses zinc as a reducing agent, resulting in the following reaction: \(RCHX-CHXR' + Zn \rightarrow RCH=CHR' + ZnX_2\). The final product is an alkene, which is a valuable and versatile compound in organic chemistry.

Step by step solution

01

Identify the vicinal dihalide

A vicinal dihalide is a compound with two halogen atoms bonded to two neighboring (vicinal) carbon atoms. A general example of a vicinal dihalide is given below: \[RCHX-CHXR'\] where R and R' represent alkyl groups, and X represents halogen atoms.
02

Choose a suitable dehalogenating agent

In order to carry out the dehalogenation, we need to find a suitable reducing agent. Common reducing agents used for this purpose are zinc (Zn) and a strong base. For this explanation, we will use zinc as the reducing agent.
03

Perform the dehalogenation

To perform the dehalogenation, the vicinal dihalide is treated with the reducing agent. Reacting the vicinal dihalide with zinc in the presence of an alcohol solvent (e.g., ethanol) will result in the removal of both halogen atoms (X) and the formation of a new double bond between the two carbon atoms. The overall balanced equation for the reaction can be represented as: \[RCHX-CHXR' + Zn \rightarrow RCH=CHR' + ZnX_2\]
04

Identify the alkene product

The product of dehalogenation is an alkene with a double bond between the two carbon atoms that were originally bonded to the halogen atoms. In our general example, the product would be: \[RCH=CHR'\] Dehalogenation of vicinal dihalides provides an efficient synthetic route to produce alkenes from readily available starting materials.

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Most popular questions from this chapter

(a) Indicate the direction of the net dipole moment for each of the dihaloethenes. (b) Would cis-2,3-dichloro-2-butane have a larger or smaller dipole moment than cis-1,2-dichloroethene? (c) Indicate the direction of the net dipolemoment of cis-1,2 dibromo-1,2-dichloroethene. Will it be larger or smaller than the dipole moment of cis-1,2-dichloroethene? Why?

How are alkenes prepared?

The dipole moment of 1,2 -dichloroethane is \(1.12 \mathrm{D}\) at room temperature. Show how one could use this dipole moment to calculate the proportions of the possible conformations that are expected to be present.

An unknown compound A rapidly decolorized a solution of bromine in carbon tetrachloride. When A was subjected to ozonolysis, the products were butanone and propanal. What might be the structure of \(\mathrm{A}\) ?

Describe dehydration of alcohols to obtain an alkene.
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