Summary - Chapter 6 review PDF

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Summary

Chapter 6 review...

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CHEM 20481 - Basic Organic Chemistry - Chapter 6 Review Alkene Reactions Stability of Alkenes In general, more highly-substituted alkenes are more stable. tetrasubstituted

>

trisubstituted >

disubstituted

>

monosubstituted

Reactions of Alkenes H C

H2 GGGGGGGGA R(R’)CH-CH3 Pt, Pd, ...

C H

syn addition

H C

HX GGGGGGGA

C H

HI >

H C

C H H

C

C H

R(R’)CX-CH3 HBr

>

HCl

HBr GGGGGGGGA radical

R(R’)CH-CH2 X

H2 O GGGGGGGGA H2 SO4

R(R’)C(OH)-CH3

Follows Markovnikov’s Rule >>

HF Anti-Markovnikov Addition

Markovnikov Addition

H C

C H

1) BH3 /THF GGGGGGGGGGGGGGGGGGGGA 2) H2 O2 , OH− , H2 O

R(R’)CH-CH2 OH

Anti-Markovnikov Addition

H C

C H

X2 GGGGGGA

R(R’)CX-CH2 X

anti addition

H C

C H

X2 GGGGGGA H2 O

R(R’)C(OH)-CH2 X O

H C

C H

peroxy acid GGGGGGGGGGGGGGGA (CH3 COOOH)

C

Markovnikov Addition

H C H

(Formation of an epoxide)

H C

C H

1) O3 GGGGGGGGGGA RC(=O)R’ + H2 C=O 2) Zn, H2 O

Products are ketone(s) and/or aldehyde(s)

Mechanisms You should know (be able to draw) the mechanisms for the following reactions. See your textbook for details. • Addition of hydrogen halides (HX) • Carbocation rearrangements during addition reactions H2 O • Acid-catalyzed hydration of alkenes (GGGGGGGGA ) H2 SO4 BH3 • Hydroboration (GGGGGGGGA ) THF • Halogenation (X 2 ) X2 • Formation of halohydrins (GGGGGGA ) H2 O...