Chemistry 108B Exam #2 Cheat Sheet-2

COHHHHOOHHOHH

C

OHO

HOO

HOOH

OR

COHHHHOOHHOHH

CH2OH

OH

OHO

COHHHHOOHHOHH

CH2OH

OHO

CH2OHOHHHHOOHHOHH

CH2OH

C

OHHHHOOHHOHH

CH2OH

OH

OHH

1) HCN2) Lindlar3) H3O(+)

Reactions of Monosaccharides

Br2, H2O pH = 6

AldaricAcid

AldonicAcid

C

OHHOHH

CH2OH

O

HHO

H

1) H2NOH2) (AcO)2, AcO(-)3) H3CO(-)

Alditol

Wohl

Killiani-Fischer

H3COO

H3COOCH3

OCH31) Ca(OH22)Fe(3+)30% H2O2Ruff

3 H2NNPh,AcOH

Osazone

N

CNH

PhNH

PhHN

HHOOHHOHH

CH2OH

2) HBr3) ROH, Ag2O4) OH(-), H2O

orH3C O CH3

O O

H3C Cl

O1)

NaBH4

HNO3

Ag2OCH3I

H3CO

HO

R OH

O

R OH

R R OH

O

CR N

R OH

O

R OH

O

R1 OR2

O

R1 OH

O

Synthesis of CARBOXYLIC ACIDS

Jones

H3O(+)

conc. H(+)

H3O(+)

conc. H(+), H2Oorconc. OH(-), H2O

KMnO4 ,

R OH

OR MgBr

H3O(+)1)2)

orO3, H2O2

R

KMnO4

H2O

CO2 NR1 Cl

O OHR2

R1 OR2

O

R1 OH

O OHR2

R1 OR2

O

R2 XR1 O(-)

O

R1 O

O

R2

Synthesis of ESTERS

conc.

R1 O

O

R1

OOHR2 R1 OR2

O

H(+)

R Cl

O

R OH

O

R Cl

O

RHO

O

R O

O

R

O+

Synthesis of ANHYDRIDES

Synthesis of ACID CHLORIDES

SOCl2or

PCl5

R Lv R CN

CR NH2

OCNR

M(+)CN(-)Synthesis of NITRILES

SOCl2

R Cl

O

R N

O

R1

R2

Synthesis of AMIDES

R1, R2 = H, alkyl, aryl, allylR = alkyl, aryl, allyl

R O

O

R N

O

R1

R2R

O

2 HNR1R2

HNR1R2

Synthesis of ANILINESNO2 NH2Fe, HCl

orSnCl2or

H2, Pd/C