Question

Draw a structure for the product of nucleophilic substitution obtained on solvolysis of tert−butyl bromide in methanol, and arrange the correct mechanism for its formation. be sure to answer all part

Answer 1

The mechanism will include

a) Slow step: rate determining step

In this step the leaving group (chloride ion) will leave the substrate and will form carbocation

b) Fast step:

The cation will be attacked by nucleophile and will give the substituted product

the mechanism is shown as :

Answer 2

Final product of the solvolysis of tert-butyl bromide in methanol is 2-methoxy-2-methylpropane.

Further Explanation:

Nucleophilic substitution reaction:

Nucleophilic substitution reaction is the chemical reaction where electron rich nucleophile replaces the leaving group from the substrate. Nucleophilic reactions are widely used in the conversion of one functional group to another.

Nucleophilic substitution reactions are two types:

1. The nucleophilic substitution reaction ${{\text{S}}_{\text{N}}}1$ is a two-step substitution reaction. In the first step, the removal of the leaving group takes place in order to form the carbocation intermediate. The second step involves the formation of the product by the attack of the incoming nucleophile on the carbocation intermediate.

2. Nucleophilic substitution reaction ${{\text{S}}_{\text{N}}}2$ is a single step substitution reaction in which electron-rich species substitute leaving group. The attack takes place from the backside of the electrophilic center thus an inversion of the configuration takes place.

The mechanism of solvolysis of tert-butyl bromide in methanol is ${{\text{S}}_{\text{N}}}1$  type (refer to the image attached), therefore

Step 1: Formation of carbocation intermediate from tert-butyl bromide after leaving of bromide ion.

Step 2: Then methanol act as the nucleophile and attack on the carbocation intermediate.

Step 3: The last step is deprotonation to produce the final product is 2-methoxy-2-methylpropane.

Learn more:

1. Product formed when 2-propanol react with NaH: brainly.com/question/5045356

2. Stereoisomer for 1,2-difluoro-1,2-dimethylcyclopentane: brainly.com/question/8803065

Answer details:

Grade: Senior School

Subject: Chemistry

Chapter: Nucleophilic substitution reactions

Keywords: Nucleophilic substitution reaction, SN1, SN2, 2-methoxy-2-methylpropane, mechanism, solvolysis, tert-butyl bromide, methanol, steps of mechanism.