Richard F. Daley and Sally J.

Daley
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Organic Chemistry
Chapter 15-A Reaction Summary II
A summary of the reactions learned in chapters 12-15

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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.

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Reaction Summary II
A summary of the reactions found in Chapters 12, 13, 14, and 15

Alcohols from alkenes (Section 14.4, page 000)

H2O H

OH

via hydroboration (Section 14.5, page 000)

1) BH3, THF 2), H2O2, NaOH

OH

via oxymercuration-demercuration (Section 14.4, page

000)
Hg(OAc)2 H2O, THF NaBH4 H2O, OH

OH

Alcohols from alkyl halides via a water nucleophile

(Section 12.10, page 000)
R X H2O R OH

X = Br, Cl, I

via hydroxide ion nucleophile (Section 12.10, page 000)

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OH

OH

X = Br, Cl, I

Alcohols from alkyl halides via a Grignard Reagent

(Section 12.13, page 000)
1) O RCH2CH2OH 2) H3O

RX X = Br, Cl, I

Mg Ether

via an organolithium reagent (Section 12.13, page 000)

1) O RCH2CH2OH 2) H3O X = Br, Cl, I

RX

Li

Aldehydes from alcohols (Section 13.12, page 000)

ClCrO3 N OH C H H H O C H

Alkanes from alkenes (Section 14.7, page 000)

H2 catalyst H C C H

Alkanes from alkyl halides (Section 15.4, page 000)

R' X R2CuLi R' R

Alkanes from alkynes (Section 14.7, page 000)

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H2 catalyst

H C H C

H H

Alkenes from alcohols (Section 13.9, page 000)

H C C OH H C C

Alkenes from alkyl halides (Section 13.8, page 000)

H C C X X = Br, Cl, I RO C C

Alkenes from alkynes via catalytic hydrogenation (Section

14.7, page 000)
H2, Pd/BaSO4 H Quinoline H C C

via dissolving metal reduction (Section 14.7, page 000)

C C Na NH3 H C C H

Alkenes from vicinal dibromides (Section 13.8, page 000)

Br C C Br I C C

Alkyl bromides from alcohols (Section 12.10, page 000)

R OH PBr3 R Br

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Alkyl chlorides from alcohols (Section 12.10, page 000)

R R OH OH SOCl2 PCl3 R R Cl Cl

Lucas reagent (Section 12.10 , page 000)

R OH HCl ZnCl2 R Cl

Alkyl halides from alcohols (Section 12.10, page 000)

R OH HX X = Cl, Br, I R X

Alkyl halides from alkenes (Section 14.3, page 000)

HX (X = Cl, Br, I)

Alkyl halides from ethers (Section 12.10, page 000)

R O R' HX X = Br, I R X + R' X

Alkyl iodides from alcohols (Section 12.10, page 000)

R OH P, I2 R I

Alkyl iodides from alkyl halides(Section 12.10, page 000)

R X NaI Acetone R I

X = Br, Cl

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Alkynes from alkyl halides (Section 12.13, page 000)

RC CH NaNH2 R'CH2Br R'CH2C CR

NH3 (33oC)

Alkynes from dihalides (Section 13.8, page 000)

R CH Br R CH Br R' KOH CH3CH2OH R C C R'

CH2CHBr2

NaNH2 NH3

CH

Amines from alkyl halides (Section 12.12, page 000)

RX NH3 (Excess) RNH2

X = Cl, Br, I

via the Gabriel synthesis (Section 12.12, page 000)

O 1) KOH, H2O 2) RBr O NH2NH2

NH

RNH2

Amines from azides (Section 12.12, page 000)

N3 1) H 2) H3O NH2

Hydride source = LiAlH4

Aryl ethers from phenols (Section 12.11, page 000)

OH RI Na2CO3 O R

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Azides from alkyl halides (Section 12.12, page 000)

X NaN3 CH3OH, H2O X = Cl, Br, I N3

Carboxylic acids from alcohols (Section 13.12, page 000)

OH H CrO3 H2SO4 O C OH

Cyclopropane from alkenes via diazomethane (Section 14.9,

page 000)
C C CH2N2

via the Simmons-Smith reagent (Section 14.9, page 000)

C C CH2I2 Zn(Cu)

Epoxides from alkenes (Section 14.8, page 000)

O RCOOH H H CHCl3 H H

Ethers from alkyl halides (Williamson ether synthesis)

(Section 12.11, page 000)
R'O

R'

Ethers from alkenes (Section 14.4, page 000)

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Hg(OAc)2

NaBH4 OH

ROH, THF H2O,

OR

Geminal dihalides from alkynes (Section 14.3, page 000)

H C C HX (X = Cl, Br) H C C X X

Halo alcohols from alkenes (Section 14.6, page 000)

X2 H2O (X = Cl, Br) X C C OH

Halogenated cyclopropanes from alkenes (Section 14.9, page

000)
C C CHX3 KOH X (X = Cl, Br) X

Hofmann elimination (Section 13.11, page 000)

R CH2CH2N(CH3)3 I Ag2O H2O R CH2CH2N(CH3)3 OH

CH

CH2

Ketones from acyl chlorides (Section 15.4, page 000)

O R' C Cl R2CuLi O R' C R

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Ketones from alcohols (Section 13.13, page 000)

OH H CrO3 H2SO4, acetone O C

Ketones from alkynes via oxymercuration-demercuration

(Section 14.4, page 000)
O H C H C

Hg(OAc)2 H2O, THF

NaBH4 H2O, OH

via hydroboration (Section 14.5, page 000)

O C C 1) BH3, THF 2) H2O, H2O2, NaOH H H C C

Nitriles from alkyl halides (Section 12.13, page 000)

R Cl KCN H2O R CN

Pinacol rearrangement (Section 13.10, page 000)

O C C H C C

OH OH

Quaternary amines from amines (Section 12.12, page 000)

RNH2 R'I (excess) RNR'3 I

Vicinal dihalides from alkenes (Section 14.6, page 000)

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X2 (X = Cl, Br)

X C C X

Vicinal diols from alkenes via epoxides (Section 14.8, page

000)
H H H3O O HO H OH H

via osmium tetroxide (Section 14.8, page 000)

OsO4 H2O, H2O2

OH OH

via permanganate ion (Section 14.8, page 000)

KMnO4 KOH, H2O

OH OH

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