cheat sheet for organic chemistry midterm 1 2015_-1
1
Chemistry 108B Exam #2 Cheat Sheet-2 C OH H H HO OH H OH H C O HO HO O HO OH OR C OH H H HO OH H OH H CH 2 OH O H O HO C OH H H HO OH H OH H CH 2 OH O HO CH 2 OH OH H H HO OH H OH H CH 2 OH C OH H H HO OH H OH H CH 2 OH O H OH H 1) HCN 2) Lindlar 3) H 3 O (+) Reactions of Monosaccharides Br 2 , H 2 O pH = 6 Aldaric Acid Aldonic Acid C OH H OH H CH 2 OH O H HO H 1) H 2 NOH 2) (AcO) 2 , AcO (-) 3) H 3 CO (-) Alditol Wohl Killiani- Fischer H 3 CO O H 3 CO OCH 3 OCH 3 1) Ca(OH 2 2)Fe (3+) 30% H 2 O 2 Ruff 3 H 2 NNPh, AcOH Osazone N C N H Ph NH Ph H N H HO OH H OH H CH 2 OH 2) HBr 3) ROH, Ag 2 O 4) OH (-) , H 2 O or H 3 C O CH 3 O O H 3 C Cl O 1) NaBH 4 Δ HNO 3 Ag 2 O CH 3 I H 3 CO HO R OH O R OH R R OH O C R N R OH O R OH O R 1 OR 2 O R 1 OH O Synthesis of CARBOXYLIC ACIDS Jones H 3 O (+) conc. H (+) H 3 O (+) conc. H (+) , H 2 O or conc. OH (-) , H 2 O KMnO 4 , R OH O R MgBr H 3 O (+) 1) 2) or O 3 , H 2 O 2 R KMnO 4 H 2 O CO 2 N R 1 Cl O OH R 2 R 1 OR 2 O R 1 OH O OH R 2 R 1 OR 2 O R 2 X R 1 O (-) O R 1 O O R 2 Synthesis of ESTERS conc. R 1 O O R 1 O OH R 2 R 1 OR 2 O H (+) R Cl O R OH O R Cl O R HO O R O O R O + Synthesis of ANHYDRIDES Synthesis of ACID CHLORIDES SOCl 2 or PCl 5 R Lv R CN C R NH 2 O CN R M (+) CN (-) Synthesis of NITRILES SOCl 2 R Cl O R N O R 1 R 2 Synthesis of AMIDES R 1 , R 2 = H, alkyl, aryl, allyl R = alkyl, aryl, allyl R O O R N O R 1 R 2 R O 2 HNR 1 R 2 HNR 1 R 2 Synthesis of ANILINES NO 2 NH 2 Fe, HCl or SnCl 2 or H 2 , Pd/C
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Transcript of cheat sheet for organic chemistry midterm 1 2015_-1
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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
