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Aldehydes, Ketones and Carboxylic Acids - Short Notes

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49 views2 pages

Aldehydes, Ketones and Carboxylic Acids - Short Notes

Uploaded by

Ayush Pal
Copyright
© © All Rights Reserved
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CHAPTER

Aldehydes, Ketones and


8 Carboxylic Acids

REDUCTION
Group Product LAH inEther NaBH4in H2O B2H6in THF H2/Catalyst∆
1°RX RH + – – +
–C≡C– –CH=CH– – – + +
>C=C< >CH–CH< – – + +
–CHO –CH2OH + + + +
>C=O >CH–OH + + + +
–CO2H –CH2OH + – + +
–CO2R –CH2OH + – + +
–COCl –CH2OH + + – +
–CONH2 –CH2NH2 + – + +
(RCO)2O RCH2OH + – + +
–CN –CH2NH2 + – + +
>C=NOH –CH2NH2 + – – +

Note:

1. B2H6 in THF not able to reduce cyclic ester.

2. NaBH4 can also reduce imine group ( ).


3. Reactivity order towards H2/Ni, ∆ ⇒ —CºN > —C—O—R

Name Reagent Function


Wolf Kishner Reduction (i) N2H4/ (ii) KOH, ∆

Clemmenson Reduction Zn–Hg/HCl

Mozingo Reduction
Stephen’s Reduction SnCl2/HCl followed by H3O+ R–C≡N R–CH=O

Rosenmund Reduction H2, Pd–BaSO4 O O

R—C—Cl R—C—H

*—CºC— —C=C—

}
H H
DIBAL-H (–78°C) —COOR
—CºN
—COOCl
—CHO
O O

—C—O—C

MPV Reduction CH3 CH3


Al —O—CH HO—CH
CH3 3 CH3
Red phosphorus in presence of HI Red P + HI

Hydroboration Reduction B2H6/AcOH, H2O

Bouvoult Blank Reduction Na/EtOH R–COO–R RCH2OH + ROH


Transfer Hydrogenation N2H4/H2O2

P
W Aldehydes, Ketones and Carboxylic Acids 23

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