This preview shows page 1. Sign up to view the full content.
Unformatted text preview: Grignard, R-MgBr, (or organometallic, R-M) additions or hydride reduction Many examples for the Grignard reactionadditions to aldehydes, ketones, esters, and acid chlorides, but all have a common mechanism for the first step; the latter cases each have a leaving group so a second addition of the organometallic can occur. Also Grignard reagents add to epoxides to yield alcohols. 3. from nucleophilic substitution reactions, S N 1 or S N 2 (more common). Reduction of carbonyl compounds gives alcohols. The two common reducing reagents are both hydride reagents, NaBH 4 and LiAlH 4 . NaBH 4 is a mild reducing reagent and only reduces aldehydes and ketones. LiAlH 4 reduces all carbonyl compounds. Thiols have many similarities to alcohols, but are appreciable more acidic (p K a 9). Oxidation of thiols can lead to sulfonic acids or disulfides depending on the oxidant....
View Full Document
- Spring '07
- Organic chemistry