310-21 - Organic Lecture Series CH 310 N LECTURE 21...

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Organic Lecture Series 1 CH 310 N LECTURE 21 Textbook Assignment: Chap 19 Begin Homework (for credit): POW 7 posted (Due Mar 21) Today’s Topics: Amides; Organometallic Reagents;reductions Notice & Announcements: Organic Lecture Series 2 Acylation Reactions to form Amides:
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Organic Lecture Series 3 Acid halides react with ammonia, 1° amines, and 2° amines to form amides – 2 moles of the amine are required per mole of acid chloride Cl O 2NH 3 NH 2 O 4 + - ++ Hexanoyl chloride Ammonia Hexanamide Ammonium chloride Reaction with Ammonia Reaction with Ammonia Organic Lecture Series 4 Acid anhydrides react with ammonia, and 1° and 2° amines to form amides –2 moles of ammonia or amine are required CH 3 COCCH 3 OO 3 3 CNH 2 O 3 CO - 4 + O + + Acetic anhydride Acetamide acetate Reaction with Ammonia Reaction with Ammonia
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Organic Lecture Series 5 • Esters react with ammonia, and 1° and 2° amines to form amides – esters are less reactive than either acid halides or acid anhydrides • Amides do not react with ammonia, or 1° or 2° amines Ph OEt O NH 3 2 O Et OH Phenylacetamide Ethyl phenylacetate + + Ethanol Reaction with Ammonia Reaction with Ammonia Organic Lecture Series 6 Acid chlorides react with salts of carboxylic acids to give anhydrides – most commonly used are sodium or potassium salts + Acetyl chloride Sodium benzoate Acetic benzoic anhydride + CH 3 CCl - OC 3 COC N a + Cl - Na + O O OO Acid Chlorides with Salts Acid Chlorides with Salts
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Organic Lecture Series 7 Reactions with Organometallic Reagents: C O OR' R Ester C O H R' R 3 o Alcohol 1) 2 eq R'MgBr 2) H 3 O + R' H OR' + C O OR' R Ester C O H R' R 3 o Alcohol 1) 2eqR 'Li 2) H 3 O + R' H OR' + C O Cl R Acid Chloride 1) (R') 2 CuLi 2) H 3 O + C O R' R Ketones Organic Lecture Series 8 –treating a formic ester with 2 moles of Grignard reagent followed by hydrolysis in aqueous acid gives a 2° alcohol HCOCH 3 O 2RMgX H 2 O, HCl HC-R R OH CH 3 + magnesium alkoxide salt A 2° alcohol An ester of formic acid + Reactions with Grignard Reagents Reactions with Grignard Reagents
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Organic Lecture Series 9 –treating other esters with a Grignard reagent followed by hydrolysis in aqueous acid gives a 3° alcohol CH 3 COCH 3 O 2RMgX H 2 O, HCl 3 C-R R OH 3 magnesium alkoxide salt + A 3° alcohol An ester of any acid other than formic acid + Reactions with Grignard Reagents Reactions with Grignard Reagents Organic Lecture Series 10 1. addition of 1 mole of RMgX to the carbonyl carbon gives a TCAI 2. collapse of the TCAI gives a ketone (an aldehyde from a formic ester) O 3 -C-OCH 3 RM g X O R OCH 3 3 -C [MgX] + 3 R O 3 O - + 1 1 + - + A magnesium salt (a tetrahedral carbonyl
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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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310-21 - Organic Lecture Series CH 310 N LECTURE 21...

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