Select your language

Suggested languages for you:
Log In Start studying!
Answers without the blur. Just sign up for free and you're in → Illustration

PROBLEM 7.81

Expert-verified
Organic Chemistry
Found in: Page 296

Short Answer

Question: When trichloride J is treated with CH3OH , nucleophilic substitution forms the dihalide K. Draw a mechanism for this reaction and explain why one Cl is much more reactive than the other two Cl’s so that a single substitution product is formed.

ANSWER

The mechanism is as follows:

The Cl adjacent to O is resonance stabilized, and the rest does not have any stabilization

See the step by step solution

Step by Step Solution

Elimination addition reaction

The elimination addition reaction is the part of nucleophilic substitution reaction in which a resonance stabilized carbocation is formed, which is then attacked by the nucleophile.

The stabilized carbocation is formed by the elimination of the good leaving group.

Explanation

The Cl adjacent to the oxygen atom in the given compound is eliminated for the formation of a stabilized carbocation. The carbocation is stabilized by the non-bonding electrons of the oxygen atom.

The other two chlorine atoms are not resonance stabilized.

After the formation of carbocation, the nucleophile attacks at this position and forms the desired product. So, the reaction is termed an elimination addition reaction

Mechanism

Recommended explanations on Chemistry Textbooks

94% of StudySmarter users get better grades.

Sign up for free
94% of StudySmarter users get better grades.