ch12B_slides_keypoints

ch12B_slides_keypoints - Ch. 12 - Chapter 12B Alcohols from...

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Unformatted text preview: Ch. 12 - Chapter 12B Alcohols from Carbonyl Compounds NOTE: Exam 4 is on Wed Dec 15 th (5:40-7:10 pm, 510N) Ch. 12 - A. Overview Today’s main goal: Grignard reaction and its application to organic synthesis Why important? Construction of carbon framework is the central challenge in organic synthesis. Grignard reaction is one of the key reactions used to assemble carbon fragments into a large framework. Ch. 12 - Key points: • Nucleophilic attack of carbanion to carbonyl (carbanion is a great nucleophile) O R O R Carbanions R-Li R-Mg-X R-C C Na R-C C Organolithium compounds Grignard reagents Acetylides R: Ch. 12 - 7C. 7C. Reactions of Grignard Reagents Reactions of Grignard Reagents with Carbonyl Compounds with Carbonyl Compounds O R R' 1. Et 2 O 2. H 3 O + + R" Mg X O H R R" R' R' = H (aldehyde) R' = alkyl (ketone) Ch. 12 - Mechanism O R R' Mg X R" + δ + δ- H O H H O H R R' R" O MgX R R' R" Ch. 12 - R, R’ = H (formaldehyde) ● 1 o alcohol O H H Mg X R + δ + δ- formaldehyde O MgX R H H OH R H H H 3 O + 1 o alcohol Ch. 12 - R = alkyl, R’ = H (higher aldehydes) ● 2 o alcohol O R' H Mg X R + δ- δ + higher aldehyde O MgX R H R' OH R H R' H 3 O + 2 o alcohol Ch. 12 - Examples O H 3 C H (2) MgI + Et 2 O CH 3 O MgI H O H H 3 O + (2 o alcohol) CH 3 Ch. 12 -Ch....
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This note was uploaded on 02/06/2011 for the course CHEMISTRY 104,224 taught by Professor Stevens,kawamura during the Spring '11 term at CUNY Hunter.

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ch12B_slides_keypoints - Ch. 12 - Chapter 12B Alcohols from...

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