organic chemistry cheat sheet for midterm2015_

Chemistry 108B Exam 2 Cheat Sheet--Woo Hoo!!!! Synthesis of ALKANES R2 R1

H2, cat. EtOH

Synthesis of HALIDES R2

R1

X2 R2 hν X = Cl, Br, I

R1

cat. = Pd/C or Pt/C

R1

R1 C C

RCH2

2 H2, cat.

R1

EtOH H2O

MgBr

R

R2

O

RCH3

O H2, cat.

R

O

OH SOCl2

R R

O

R

1) Hg(OAc)2 (aq) 2) NaBH4

R

1) BH3, THF 2) NaOH/H2O2

R

HX R

R2

R

X

HX R2

Synthesis of ALCOHOLS X

N

O

X

R

R

R

N

R1

Br

R

R

Lv = Cl, Br, I, OTos

NBS R

OH conc. H(+)

R

R

R

N

R3

Ph3P C

R1

R2

H

H

R1

-78 °C R1 C C

R1 C C

Br

X = Cl, Br, I

H2 R2 Lindar's cat. R1

RX, AlX3

R2

R1

Li, NH3

R2

+

-78 °C

R1

2 NaNH2, NH3

O

Cl

R

HNO3/H2SO4

R1 C

-78 °C

Br

R

O AlCl3 R

R2

Synthesis of ALKYNES R2

X

C

NO2

S o

m

m

Synthesis of EPOXIDES O R

R1

O O

R

R1

O

R2 O

OH

R2 HO R

R2

R1

R1

O

R

R1

R2

+

R2

R1

OH

O PCC or Jones or R1 R2 R2 NaOCl

Lv R1

RNH2

R C C

R2

O

OR2

R3

R2

R2

Cl

R4

R1

R

HgSO4, H3O(+) or R 1) R2BH 2) H2O2, NaOH

O3 or KMnO4/H(+)

O

NR R1

R

O

AlCl3

For R C C H : HgSO4 = R1

R1

H(+)

O

+

Synthesis of IMINES

O

OH(-) X

OH

OsO4 or KMnO4/OH(-)

Synthesis of ALDEHYDES/KETONES O PCC R OH or R H Dess-Martin

R

R2CH2

OH

R1 R1

S = substituent o = ortho m = meta p = para

1) Hg(OR2)2, R2OH 2) NaBH4

R2

R1

X2/H2O R

R1

R1 O(-)

OH

H3O(+)

Synthesis of ETHERS O

OH

OH

R1

SO3H

p R2

OH

OH(-)

R1

o

R2

OH

SO3/H2SO4

R2

OH

R1

O

E. A.S. Reactions X2, FeX3

R1 OH

R1

Li, NH3

OH

R2MgBr

O

X

R

LiAlH4

R1

R

R

R2

BH3 or LiAlH4

OR2 O

X

X2

R2 R3

OH

R1

X

FeX3

R3

R1

R2

O

R X2

, 0 °C O

Br

NBS

R2 OH

R3MgBr

R

Br

R

POCl3

OH

R1

O

R

OH

H

R1

For 3° ROH's: conc. HX, 25 °C

R2

R2MgBr

O

R

R

R1

R2

R1

Synthesis of ALKENES NaOH

OH

R

NaBH4

O OH PBr3

OH

R

OH

O Cl

R

H

R R

Lv

NaBH4

OH

R

O R

CH3

R2BH =

R3

+

O R1

O

R

O R1

R22CuLi Cl

O

R2

H

O R2

R4