Chemistry 108B Exam 2 Cheat Sheet--Woo Hoo!!!!

Synthesis of ALKANES
R2
R1

H2, cat.
EtOH

Synthesis of HALIDES
R2

R1

X2
R2
h
X = Cl, Br, I

R1

cat. = Pd/C or Pt/C

R1

R1 C C

RCH2

2 H2, cat.

R1

EtOH
H2O

MgBr

R2

RCH3

O
H2, cat.

OH SOCl2

R
R

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

1) BH3, THF
2) NaOH/H2O2

HX
R

R2

HX
R2

Synthesis of ALCOHOLS
X

R1

Br

Lv = Cl, Br, I, OTos

NBS
R

OH conc. H(+)

R3

Ph3P C

R1

R2

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

Cl

HNO3/H2SO4

R1 C

-78 C

Br

O AlCl3
R

R2

Synthesis of ALKYNES
R2

NO2

S
o

Synthesis of EPOXIDES
O
R

R1

O
O

R1

R2
O

OH

R2
HO
R

R2

R1

R1

R1

R2

R2

R1

OH

O
PCC or Jones
or
R1
R2
R2
NaOCl

Lv
R1

RNH2

R
C C

R2

OR2

R3

R2

R2

Cl

R4

R1

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

O3
or
KMnO4/H(+)

NR
R1

AlCl3

For R C C H : HgSO4 =
R1

R1

H(+)

Synthesis of IMINES

OH(-)
X

OH

OsO4
or
KMnO4/OH(-)

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

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

R2

OH

SO3/H2SO4

R2

OH

R1

E. A.S. Reactions
X2, FeX3

R1
OH

R1

Li, NH3

OH

R2MgBr

LiAlH4

R1

R2

BH3
or
LiAlH4

OR2
O

X2

R2
R3

OH

R1

FeX3

R3

R1

R2

R
X2

, 0 C
O

Br

NBS

R2
OH

R3MgBr

Br

POCl3

OH

R1

OH

R1

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

R2

R2MgBr

R1

R2

R1

Synthesis of ALKENES
NaOH

OH

NaBH4

O
OH PBr3

OH

OH

O
Cl

R
R

Lv

NaBH4

OH

O
R

CH3

R2BH =

R3

O
R1

O
R1

R22CuLi
Cl

R2

O
R2

R4

Chemistry 108B Exam #2 Cheat Sheet-2

Synthesis of CARBOXYLIC ACIDS
O
OH

R
R

MgBr

OH

KMnO4
H3O(+)

R
N

R
O
R1

OR2

conc. H(+), H2O

or
conc.

OH(-),

R1

H2O

R1

R2

OH

OR2

R1

Cl
O

R1

OH conc. H(+)
R2

OR2

O(-)

R1

O
R

SOCl2
or
PCl5

OH

R2

HNR1R2
R

R2

R1

Synthesis of ANILINES

R2

Synthesis of ACID CHLORIDES

OH

NO2

R = alkyl, aryl, allyl

R1, R2 = H, alkyl, aryl, allyl

OR2

OH

R1

2 HNR1R2

R1

R2 OH

OH

conc. H(+)
R
H2O

R1

O
O

OH

R1

Cl

R1

R2 OH

KMnO4 , H3O(+)
or
O3, H2O2

R1

2) H3O(+)
R

OH
O

1) CO2

Synthesis of AMIDES

Synthesis of ESTERS

Jones

Cl

Fe, HCl
or
SnCl2
or
H2, Pd/C

NH2

Synthesis of NITRILES
R

M(+)CN(-)

Lv
O

SOCl2

Synthesis of ANHYDRIDES
R
R

CN

O
R

CN

Cl

HO

NH2

Reactions of Monosaccharides
HO
HO
HO
CH2OH
H
HO
H
H

Alditol

KillianiFischer
H
H
H
HO
H
H

OH
H
OH
OH
CH2OH

O
OH
OH
H
OH
OH

O
OR
OH

or

H3C O
CH3 H3C
2) HBr
3) ROH, Ag2O
4) OH(-), H2O

NaBH4

1) HCN
2) Lindlar
3) H3O(+)

Ph 3 H2NNPh,
AcOH
N NH
H
H
C
N Ph
N
CH2OH
H3CO
H
HO
H
OH
Osazone
H3CO
H
OH
H3CO
CH2OH

1)

H
H
HO
H
H

Cl
HO

HNO3

OH
H
OH
OH

O
C

H
HO
H
H

OH
H
OH
OH

Aldaric
Acid

C
HO

Br2, H2O
pH = 6

CH2OH

1) H2NOH
2) (AcO)2, AcO(-)
3) H3CO(-)
Ag2O
CH3I

Wohl H
HO

O
OCH3
OCH3

O
C
H

OH

OH
CH2OH

HO
H
HO
H
H

O
C
OH
H
OH
OH

Aldonic
Acid

CH2OH
1) Ca(OH2
2)Fe(3+)
Ruff 30% H2O2