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Chapter 15: Alcohols, Diols and Thiols



Overview | Hydration of Alkenes | Hydroboration-Oxidation of Alkenes | Oxymercuration-Demercuration of Alkenes | Hydrolysis of Alkyl Halides | Reactions of RLi and RMgX with Aldehydes and Ketones | Reduction of Aldehydes and Ketones | Reaction of RLi or RMgX with Esters | Reduction of Carboxylic Acids and Esters | Ring opening of Epoxides |


Hydroboration / Oxidation of Alkenes

Chapter 15: Alcohols, Diols and Thiols

Hydroboration / Oxidation of Alkenes (review of Chapter 6)

hydroboration of C=C
Reaction type: Electrophilic Addition

Summary.

Related Reactions
MECHANISM FOR REACTION OF ALKENES WITH BH3
Step 1:
A concerted reaction. The p electrons act as the nucleophile with the electrophilic B and the H is transferred to the C with syn stereochemistry.
addition of HBr to C=C
Step 2:
First step repeats twice more so that all of the B-H bonds react with C=C
Step 3:
Peroxide ion reacts as the nucleophile with the electrophilic B atom.
Step 4:
Migration of C-B bond to form a C-O bond and displace hydroxide. Stereochemistry of C center is retained.
Step 5:
Attack of hydroxide as a nucleophile with the electrophilic B displacing the alkoxide.
Step 6:
An acid / base reaction to form the alcohol.


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