Chemistry 108B Exam #2 Cheat Sheet-2

Synthesis of CARBOXYLIC ACIDS

O Synthesis of ESTERS Synthesis of AMIDES
Jones
R OH R OH O O O
R2 OH O
O
R1
2 HNR1R2 R2
1) CO2 R1 Cl N OR2 R Cl R N
R MgBr R OH
2) H3O(+) O O O R1
R O R2 OH O O HNR1R2 O
KMnO4 , H3O(+) R1 O R1 R1 OR2
R2
or R OH R O R R N
R O O
O3, H2O2 R2 OH
R = alkyl, aryl, allyl R1
O R1 OH conc. H(+) R1 OR2
KMnO4 R1, R2 = H, alkyl, aryl, allyl
O O
R H3O(+) OH R2 X
O R1 O(-) R1 O R2 Synthesis of ANILINES
conc. H(+)
R C N NO2 NH2
H2O R OH Fe, HCl
O Synthesis of ACID CHLORIDES or
conc. H(+), H2O O
SnCl2
or O SOCl2 O
R1 OR2 R1 OH or
conc. OH(-), H2O or H2, Pd/C
R OH R Cl
PCl5

Synthesis of NITRILES
Synthesis of ANHYDRIDES
M(+)CN(-)
R Lv R CN O O O O
O
SOCl2
+
C R CN R Cl HO R R O R
R NH2

Reactions of Monosaccharides
HO O O O
O 1) or
HO OR H3C O CH3 H3C Cl
HO 2) HBr
OH 3) ROH, Ag2O
CH2OH HO O
4) OH(-), H2O C
Alditol H OH
H O H OH
HO H NaBH4 Aldaric
C HNO3 HO H
H OH Acid
H OH Δ H OH
H OH
HO H H OH
Killiani- CH2OH
Fischer 1) HCN H OH C
2) Lindlar H OH HO O
H O 3) H3O(+)
C CH2OH Br2, H2O
pH = 6 HO O
H OH C
1) H2NOH
H OH Ph 3 H2NNPh, H OH
2) (AcO)2, AcO(-) Aldonic
HO H AcOH
H N NH 3) H3CO(-) HO H Acid
H OH C H Ag2O H OH
Wohl H O
H OH N Ph C
CH3I H OH
N
CH2OH H3CO HO H CH2OH
HO H
O
H OH H OH 1) Ca(OH2
Osazone H3CO OCH3
H OH 2)Fe(3+)
H3CO H OH
OCH3 Ruff 30% H2O2
CH2OH CH2OH