You are on page 1of 8

Richard F. Daley and Sally J.

Daley
www.ochem4free.com

Organic Chemistry
Chapter 8-A Reaction Summary I
A summary of the reactions learned in Chapters 7-8

Organic Chemistry - RS I

423

Daley & Daley

Copyright 1996-2005 by Richard F. Daley & Sally J. Daley All Rights Reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, or otherwise, without the prior written permission of the copyright holder.

www.ochem4free.com

5 July 2005

Organic Chemistry - RS I

424

Daley & Daley

Reaction Summary I
A summary of the reactions found in Chapters 7 and 8

Acetal formation (Section 7.5, page 000)


OH C O ROH, H H3O Hemiacetal C OR ROH, H H3O Acetal OR C OR

Acyl chloride synthesis via inorganic acid chlorides


(Section 8.3, page 000)
O C Inorganic OH acid chloride O C Cl

Inorganic acid chloride = SOCl2, PCl3, or PCl5

via oxalyl chloride (Section 8.3, page 000)


O O C OH Cl C O C Cl O C Cl

Addition of carbon nucleophiles to aldehydes and ketones (Section 7.8, page 000)
RLi or RMgX H3O

OH

Addition of carbon nucleophiles to carboxylic acid derivatives (Section 8.6, page 000)

www.ochem4free.com

5 July 2005

Organic Chemistry - RS I

425

Daley & Daley

O C L RLi or RMgX H3O

OH C R R

L = OR or acyl group O C OH RLi H3O

O C R

Addition of carbon nucleophiles to nitriles (Section 8.7, page


000)
O CN RLi or RMgX H3O C R

Amide synthesis (Section 8.4, page 000)


O C L NH O C N

L = Cl or acyl group

Amine synthesis (Section 7.7, page 000)


NH 1) NaCNBH3 2) H3O NH2

Anhydride synthesis (Section 8.3, page 000)


O COH O CCl O C O O C

or
O COH O (CH3C)2O O C O O C

www.ochem4free.com

5 July 2005

Organic Chemistry - RS I

426

Daley & Daley

Baeyer-Villiger oxidation (Section 8.8, page 000)


O C O CF3COOH O C O

Cyanohydrin reaction (Section 7.4, page 000)


HCN OH C CN

Enamine formation (Section 7.6, page 000)


R2NH, H H3O C

C C H

NR2

Ester synthesis (Section 8.2, page 000)


O C L ROH O C OR

L = Cl, OH, or acyl group

Ester hydrolysis (Section 8.2, page 000)


O C OR H3O (or OH, H2O) O C OH + ROH

Fischer esterification (Section 8.2, page 000)


O C OH ROH, H O C OR

Grignard reagent formation (Section 7.8, page 000)

www.ochem4free.com

5 July 2005

Organic Chemistry - RS I

427

Daley & Daley

Br

Mg Ether

MgBr

Imine formation (Section 7.6, page 000)


C O RNH2, H H3O C

NR

Nitrile hydrolysis (Section 8.7, page 000)


O CN H2O ( OH or H ) C NH2 H2O ( OH or H ) O C OH

Organolithium reagents from alkyl halides (Section 7.8, page


000)
Li Ether or hexane

Br

Li

Reduction of acyl halides (Section 8.5, page 000)


O CCl 1) LiAl(OC(CH3)3)3H 2) H3O O CCl O CH

1) NaBH4 2) H3O

CH2OH

Reduction of a ketone or aldehyde (Section 7.7, page 000)


1) H 2) H3O

OH

H = LiAlH4 or NaBH4

www.ochem4free.com

5 July 2005

Organic Chemistry - RS I

428

Daley & Daley

Reduction of an amide (Section 8.5, page 000)


O C NH2 1) H 2) H3O H = LiAlH4

CH2NH2

Reduction of a nitrile (Section 8.7, page 000)


1) H 2) H3O H = LiAlH4

CN

CH2NH2

Reduction of carboxylic acids and esters (Section 8.5, page


000)
O C L 1) H 2) H3O L = OH or OR H = LiAlH4 CH2OH

Synthesis of a carboxylic acid (Section 7.8, page 000)

C or

MgBr O 1) CO2 2) H3O C C OH

Li

Wittig reaction (Section 7.10, page 000)

www.ochem4free.com

5 July 2005

Organic Chemistry - RS I

429

Daley & Daley

R C R O

Ph Ph P Ph

R' C R' R C R C R' R'

www.ochem4free.com

5 July 2005