R1

R2

R1R2CR1 R2C

MgBrRCH2 RCH3

R1R2

RLv

R

R OH R

R1 R2

O Ph3P C

R1 R2

HR3

ROH R

CR1 R2C

R1

R2

R1 R2

CR1 R2CR1R2

Br

Br

R1 R2R1 R2

X

R O

R OR RO

R

X

RX

ROH

ROH

N

RCl

RBr

X

RR

Br

R R

Br

R RX

X

R

R

R

OH

ROH

R H

O

R1 R2O

R1 R2

OH

R1 H

O

R1 R2O

R1 R2OH

R1 R2OH

R3

R1 OR2O

O

R1R1

OHR2

R1

R2

R1OH

R2

OH

O

R1R1

OHOH

Synthesis of ALKANES

Synthesis of ALKENES

Synthesis of ALKYNES

LvR2CH2R1 O(-)

Synthesis of ALCOHOLSSynthesis of HALIDESChemistry 108B Exam 2 Cheat Sheet--Woo Hoo!!!!

OR1R2

H2, cat.

R1

cat. = Pd/C or Pt/C

2 H2, cat.

R1

OR2

R OH

Lv = Cl, Br, I, OTos

conc. H(+)

, 0 C

-78 CLi, NH3

-78 CLi, NH3

-78 C2 NaNH2, NH3

Synthesis of ETHERS

hX = Cl, Br, I

For 3 ROH's: conc. HX, 25 C

2) NaBH4

R1 OH

1) BH3, THF

1) Hg(OAc)2 (aq)

2) NaOH/H2O2

OsO4or

KMnO4/OH(-)

OH(-)

O

R1R1

OHOH

2) NaBH41) Hg(OR2)2, R2OH

R OH

O

Lindar's cat.

R OHor

R

O

RH2, cat.

CR1 R2C

H

R3

H3O(+)

EtOH

H2O

EtOH

NaOH

POCl3

H2

X2

HX

HX

SOCl2

PBr3

NBS

X2FeX3

NBS

X2

NaBH4

NaBH4

R2MgBr

R3MgBr

R2MgBr

BH3

LiAlH4LiAlH4

R H

OR OH

R1

R4

R2

R3 R1 R3

OR2 R4

O

CR RC R

OR

CR HC R CH3O

R HO

orKMnO4/H(+)

Synthesis of ALDEHYDES/KETONES

+

HgSO4, H3O(+)or

1) R2BH2) H2O2, NaOH

R2BH =For HgSO4 =

R1 R2O

R1 R2

OH PCC or Jonesor

NaOCl

:

PCC

O3

R Cl

O

R

O+ AlCl3

N

R1

R2

R1 R2

R OO

OH

R OO

OH

O

R1 R2O

R1 R2

R R XHO O

R

Synthesis of EPOXIDES

OH(-)X2/H2O

X

R

R Cl

O

R

O

NO2

SO3H

E. A.S. ReactionsX2, FeX3

X = Cl, Br, IRX, AlX3

+

HNO3/H2SO4

SO3/H2SO4

AlCl3

So

mp

S = substituento = orthom = metap = para

o

m

N

R1 Cl

O R22CuLiR1 R2

OSynthesis of IMINES

R1 R2O

+ RNH2R1 R2

NRH(+)

orDess-Martin