Week+5+Handout (1)

Week+5+Handout (1) - Week 5 Handout CHEM 35 Sections 6, 9...

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Week 5 Handout CHEM 35 Sections 6, 9 and 16 TA: Brian Loy Carboxylic Acids: (from lecture) 1. Nucleophilic Addition Weaker Nucleophiles such as NaBH 4 and R-MgBr are NOT strong enough to react with carboxylic acids by nucleophilic addition to the carbonyl. 2. Decarboxylation R C O OH Acid/Base Proton Transfers Nucleophilic Addition α -Carbon Reactions Decarboxylation C O OH 1. R-Li 2. H 3 O + OH R R C O OH 1. LiAlH 4 2. H 3 O + OH Tertiary Alcohol (two new “R” groups) Primary Alcohol R O O OH R' = α β β -carbonyl compound R O O H O R' R O H R' C O O "Enol" R O R' "Keto"
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Page 2 3. Substitution Reactions A common substitution reaction mechanism of carboxylic acids (and of their derivatives) is called Addition-Elimination: LG = leaving group Nuc = nucleophile Types of Carboxylic Acid Derivatives you will see in this course: Acid Halides Carboxylic Esters Acid Anhydrides
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This note was uploaded on 11/24/2010 for the course CHEM 35 taught by Professor Dubois,j during the Spring '07 term at Stanford.

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Week+5+Handout (1) - Week 5 Handout CHEM 35 Sections 6, 9...

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