Q7-16P - Organic Chemistry (Mcmurry)

Question

Predict the products of the following reactions:

Step-by-Step Solution

Answer

(a) 

(b)

(c)

(d)

Step-by-Step solution Step 1: Electrophilic addition of HX to an alkene

In the addition of HX to an alkene, the significantly substituted carbocation is generated as an intermediate than the less substituted carbocation. It follows the Markovnikov Rule. The rule tells that the negative portion of the adding molecule gets connected to a carbon atom that comprises lesser hydrogen atoms.

Step 2: Predicting the product of reaction (a)

(a)The electrophilic addition of HCl to the given alkene produces an alkyl chloride. Cyclohexene reacts with HCl to form chlorocyclohexane. The reaction can be given as:

Product of reaction (a)

(b)The electrophilic addition of HBr to the given alkene produces an alkyl halide. 2-methylpent-2-ene reacts with HBr to produce 2-bromo-2-methylpentane. The reaction can be given as:

Predicting the product of reaction (b)

(c)The given alkene reacts with ${\text{H}}_{\text{2}}\text{O}$ and ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ to form an alcohol. The compound, 4-methylpent-1-ene reacts with ${\text{H}}_{\text{2}}\text{O}$ and ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$to form 4-methylpentan-2-ol. The reaction can be given as:

 

Predicting the product of reaction (c)

(d)The electrophilic addition of HBr to methylenecyclohexane produces 1-bromo-1-methylcyclohexane. The reaction can be given as:

Reaction (d)