Leila Section Week 2

Leila Section Week 2 - Chemistry 35 Organic Monofunctional...

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Chemistry 35: Organic Monofunctional Compounds Section 2: October 6, 2008 Prof. Huestis, Fall 2008 TA: Leila Yeh Beach Aldehydes and Ketones: Reactions with Weak Nucleophiles H 2 O, ROH Very weak nucleophiles; acid or base catalysis required to push these reactions along at an appreciable rate. Acid catalysis activates carbonyls toward nucleophilic attack by increasing the electrophilicity of the carbonyl carbon. Acid Catalyzed Nucleophilic Addition/Elimination: A Stepwise Mechanism O H 3 O + OH -H 2 O OH This carbon now strongly activated toward nucleophilic attack! H O H 3 O + H OH -H 2 O H OH ROH H ORH HO H 2 O -H 3 O + H OR HO H 3 O + -H 2 O ALDEHYDE HEMIACETAL H OR + H 2 O ROH H OR HRO H 2 O -H 3 O + H OR RO ACETAL H 3 O + -H 2 O H ORH RO -ROH H OR H OR H 2 O H RO OH 2 + H 2 O -H 3 O + H RO OH HEMIACETAL H 3 O + H HRO OH H OH H OH H 2 O -H 3 O + H O ALDEHYDE -H 2 O H OR H OR -H 2 O -ROH -H 2 O
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Notes: Acid catalyzed nucleophilic addition/elimination reactions allow you to access hemiacetals
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This note was uploaded on 02/13/2009 for the course CHEM 35 taught by Professor Dubois,j during the Fall '07 term at Stanford.

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Leila Section Week 2 - Chemistry 35 Organic Monofunctional...

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