Question

For the following SN2 reaction, draw the organic and inorganic products of the reaction, and identify the nucleophile, substrate, and leaving group. Include wedge/dash bonds and H on a stereocenter.

Select the statement that property identifies the nucleophile, substrate, and leaving group.  

• Cl- is the substrate. CH3CH(CH2)2CH3Cl is the nucleophile, and CN- is the leaving group.  

• CH3CH(CH2)2CH3Cl is the substrate. CN- is the nucleophile. and Cl- is the leaving group.  

• CN- is the substrate. Cl- is the nucleophile, and CH3CH(CH2)2CH3Cl is the leaving group.

Answer 1

Concepts and reason

Two compounds are given which are undergoing ${{\rm{S}}_{\rm{N}}}2$ reaction whose product needs to identified as organic and inorganic. Also, nucleophile, leaving group, and substrate needs to be identified.

In ${{\rm{S}}_{\rm{N}}}2$ reaction nucleophile attacks the haloalkane, that is, a substrate of the reaction and halogen leaves as a leaving group. Then provide the distinction between the organic and inorganic product formed. Generally, organic compounds always contain carbon atom.

Fundamentals

${{\rm{S}}_{\rm{N}}}2$ reaction is bimolecular nucleophilic substitution reaction which takes place between a haloalkane which act as a substrate and a nucleophile. The reaction takes place in one step through a transition state. Consider the following scheme of a ${{\rm{S}}_{\rm{N}}}2$ reaction:

Basic elements in the reaction are as follows:

1.Nucleophile: Nucleophile means the atom or compounds which have affinity for protons or positive charge. They are generally rich in electron density, that is, either they are negatively charged or attached with the electron donating groups that increases the electron density on the site. Atoms which contain lone pair also act as electron rich site. Consider the following example of a nucleophile:

2.Leaving group: It is the one which leaves the compound by taking the electron density and should be capable to stabilize the electron density carried by it. Thus, halogens being the electronegative atoms can stabilize the extra electron density and hence act as good leaving group.

3.Substrate: It is the compound on the substitution is carried out.

Identify the given compounds as nucleophile, substrate, and leaving group as shown below:

Write the product of the given reaction and mark them as organic product and inorganic product of the reaction as shown below:

Ans:

The organic and inorganic product of the reaction is marked as follows: