Reduction_Handout_2009 - Alkane Alkane R(H) O Benzylic...

Info iconThis preview shows pages 1–3. Sign up to view the full content.

View Full Document Right Arrow Icon
R R R R R R R R N N R R N N H H H R C N R NH 2 Substrate Products Reducing Agents H 2 , cat: Pd , Pt, Ru, or Ni R R H 2 , Lindlar catalyst Na/NH 3 (liquid) or Li/NH 3 (liquid) trans-alkene H 2 , Pd/C H 2 , Pd/C H 2 , Pd/C Alkene Alkane Alkyne Alkyne cis-alkene Enamine Amine Imine Amine Nitrile Primary Amine R C N R H Nitrile Aldehyde O 1. (i-Bu) 2 AlH (DIBAH), low temp (-78°C) 2. H 2 O R R R R H H Alkyne cis-alkene 1. R 2 BH 2. H + (acetic acid) May be adsorbed on charcoal (C) (Pd/CaCO 3 ) Hydroboration - Protonation Name (Work-up, conditions and solvents are omitted) NaBH 3 CN LiAlH 4 LiAlH 4 LiAlH 4 NaBH 4 NaBH 4 [NaBH(OAc) 3 ] NaBH(OAc) 3 NaBH(OOCCH 3 ) 3 =
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
R(H) O R(H) OH R(H) O R(H) Raney Ni Na[Hg], HCl H 2 NNH 2 , KOH, ! H(R) O NaBH 4 , CeCl 3 , low Temp (-15°C) H(R) OH R(H) O R(H) Ketone or aldehyde Secondary or primary alcohol Aldehyde or ketone Secondary or primary alcohol Ketone or aldehyde Ketone or aldehyde Wolff-Kishner Clemenson NO 2 NH 2 Nitro comppund Amine H 2 , Pd/C Sn, HCl Fe, HCl
Background image of page 2
Background image of page 3
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Alkane Alkane R(H) O Benzylic ketone or aldehyde H 2 , Pd/C R(H) (H 2 /Ni) Catalytic hydrogenation NO 2 NO 2 NH 2 NO 2 Selective NO 2 reduction Substrate Products Reducing Agents Name (Work-up, conditions and solvents are omitted) LiAlH 4 NaBH 4 (NH 4 ) 2 S OH O OH NR 2 O NR 2 OR O OH + ROH OR O H O Cl O OH Cl O H O Carboxylic Acid Primary Alcohol Amide Amine Ester Primary Alcohol Ester Aldehyde Acid Chloride Primary Alcohol Aldehyde (i-Bu) 2 AlH (DIBAH) LiAlH(t-BuO) 3 LiAlH(t-BuO) 3 DIBAH Cl O H O Aldehyde H 2 , Pd/BaSO 4 Rosenmund Reduction Substrate Products Reducing Agents Name (Work-up, conditions and solvents are omitted) Acid Chloride Acid Chloride LiAlH 4 LiAlH 4 LiAlH 4 LiAlH 4...
View Full Document

This note was uploaded on 05/13/2010 for the course CHEM ORGANIC CH taught by Professor Dotsevisogah during the Spring '09 term at Cornell University (Engineering School).

Page1 / 3

Reduction_Handout_2009 - Alkane Alkane R(H) O Benzylic...

This preview shows document pages 1 - 3. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online