Halloween Review

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Halloween Review

O

H

Cl

CuLi

Li

(i)

O

ether

Mg

ether

CH 3

(ii) H 3O +

(i) mCPBA

(ii) H 3O +

(ii) H 3O +

CH 3

Br

OH

OH

OH

OH

CH 3

CH 3


S

S

O

O

S S

H

H

S

S

CH 3NH 2

H +

H +

OH

(i) n-BuLi

(ii) CH 3I

Ni

H 2

N

O O

S S

H


H 3C

O HS

N

N

Br

H +

O

H +

Cu

Li +

OH

D 2

Lindlar

S O

N

N

D D


O

S S

O

CH 3

O

KCN

(i)

H +

HgCl 2

(i)

H 2O

(ii) H +

MgBr

(ii) H +

HO CN

Li

O

HO

CH 3

OH


H 3C

O

O

H

H 2 / Pt

O PPh 3

O

O

CH 3

+

HO OH

H +

Zn/(Hg)

HCl / H 2O

OH

O O


H

H 3C

O

O

O

CH 3

H 2

H +

"Ru

RhCl(PPh 3) 3

MeO

O

NH

NaH

"

+

PPh3 O

MeO

N

O

H


Br

O

Me 2CuLi

ether

O 3

Me 2S

HO OH

N

HCl / H 2O

H +

O O

O

O

O

+ H3N


H

N

CH 3

O

HO H

CH 2I 2

Zn/Cu

CH 2I 2

Zn/Cu

NaBH 4

MeOH

H +

H

NH

CH 3

O OH


H

O

O

O

H

H

Br

CH 3

NaH

RCM

(i) PhMgBr

(iI) H 3O +

ether

+

PPh3 CuLi

2

H

OH

Ph

H

CH 3

H


C

H

O

O

O

H 2NNH 2

KOH

NaBH 4

CH 2I 2

Cu/Zn

MeOH

H +

NH 2

C

H

N

OH


O

H

OH

OH

OH

O

CH 3

OH

H

O

O 3

Me 2S

(i) EtMgBr

(ii) H 3O +

H 2CrO 4

H 2CrO 4

O

O

HO

O

O

H

O

OH

O

OH

OH

OH

CH 3


HO

O O

O

O

O

H

sia

sia

LiAlH 4

ether

(i) EtMgBr

(ii) H 3O +

(i) EtMgBr

(ii) H 3O +

(i) Me 2CuLi

(ii) H 3O +

HO

HO

OH OH

O

OH

sia

sia


Br

O

O

O

H

CH 3

H

Br

PPh 3

(i) LiAlH 4

(ii) H 3O +

Li

pentane

NaH

Li

OH

OH

CH 3

H

Li


H

O

HO

O

OH

O

OH

Me 2S

+ –

CH2 H +

HIO 4

OH

PCC

H

O

O

O

O

O O

H


mCPBA

O

O

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