310-17 - Organic Lecture Series CH 310 N LECTURE 17...

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Organic Lecture Series 1 CH 310 N LECTURE 17 Textbook Assignment: Chap 17 finish Homework (for credit): POW 5 posted (Due Feb 28) Today’s Topics: Preparation -COOH; Fisher esterification Notice & Announcements: Exam 1-grading in progress “Heart Transplants & Heart Assist Devices” “Heart Patients Perspective” Bill Kessler, M.D. - Cardiothoracic Surgery Joined by a Panel of Patients Organic Lecture Series 2 Carboxylic Acids Carboxylic Acids Chapter 17
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Organic Lecture Series 3 • Carbonation of Grignard reagents – treatment of a Grignard reagent with carbon dioxide followed by acidification gives a carboxylic acid MgBr C O O C-O - [MgBr] + O HCl H 2 O C-O H O Mg 2+ A magnesium carboxylate Cyclopentane- carboxylic acid + Carbon dioxide + Preparation Preparation Organic Lecture Series 4 Reduction Reduction • The carboxyl group is very resistant to reduction – it is not affected by catalytic hydrogenation under conditions that easily reduce aldehydes and ketones to alcohols, and reduce alkenes and alkynes to alkanes; it is not reduced by NaBH 4 Lithium aluminum hydride reduces a carboxyl group to a 1° alcohol – reduction is carried out in diethyl ether, THF, or other nonreactive, aprotic solvent COH O 1. LiAlH 4 2. H 2 O CH 2 OH LiOH Al( OH) 3 + + 4-Hydroxymethyl- cyclopentene
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Organic Lecture Series 5 – carboxyl groups are not affected by catalytic reduction under conditions that reduce aldehydes and ketones – nor are carboxyl groups reduced by NaBH 4 OH O O H 2 Pt O
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This note was uploaded on 04/24/2011 for the course CH 56255 taught by Professor Colapret during the Spring '11 term at University of Texas at Austin.

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310-17 - Organic Lecture Series CH 310 N LECTURE 17...

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