cheat sheet for organic chemistry midterm 1 2015_-1

Chemistry 108B Exam #2 Cheat Sheet-2 Synthesis of CARBOXYLIC ACIDS O OH

R R

R

MgBr

OH

KMnO4 H3O(+)

R N

C

R O R1

OR2

conc. H(+), H2O or conc.

OH(-),

R1

H2O

R1

O

R2

OH

OR2

R1

R

Cl O

R

R1

OH conc. H(+) R2

O

OR2

O

O(-)

R1

O R

O

SOCl2 or PCl5

OH

R2

O

HNR1R2 R

R

N

R2

R1

Synthesis of ANILINES

R2

O

Synthesis of ACID CHLORIDES OH

N

O

X

NO2

O

R

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

OR2

OH

R1

2 HNR1R2

R1

O

R2 OH

O

OH

conc. H(+) R H2O

R1

O

O

O

O

O

O O

OH

R1

N

Cl

R1

R

O

R2 OH

O

O

KMnO4 , H3O(+) or O3, H2O2

R

R1

R

2) H3O(+) R

O

OH O

1) CO2

Synthesis of AMIDES

Synthesis of ESTERS

Jones

R

Cl

Fe, HCl or SnCl2 or H2, Pd/C

NH2

Synthesis of NITRILES R

M(+)CN(-)

Lv O

R

SOCl2

C

Synthesis of ANHYDRIDES R R

CN

O R

CN

Cl

+

O

O

O

HO

R

R

NH2

R

O

Reactions of Monosaccharides HO HO HO CH2OH H HO H H

Alditol

KillianiFischer H H H HO H H

C

OH H OH OH CH2OH

O OH OH H OH OH

O OR OH

O

O

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

O

1)

H H HO H H

C

O

Cl HO

HNO3

Δ

OH H OH OH

O C

H HO H H

OH H OH OH

Aldaric Acid

C HO

O

Br2, H2O pH = 6

CH2OH

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

Wohl H HO

O OCH3 OCH3

O C H

H

OH

H

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