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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

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