Protective Groups for Ketones and Aldehydes

Used to protect carbonyl functions from unwanted nucleophilic attack

note: will not work for carboxylic acids, esters, or amides!

1 Chemistry 335 Supplemental Slides: Protective Groups in Organic Chemistry

Protective Groups for Alcohols
1. Silyl groups

2 Chemistry 335 Supplemental Slides: Protective Groups in Organic Chemistry

Protective Groups for Alcohols
1. Silyl groups

protective group abbreviation comments

- useless protecting group!

Me3Si or TMS
- hydrolyzes on silica gel

- better
Et3Si or TES - stable to chromatography
- removed quickly with acid

- fantastic!
TBDMS or TBS - most commonly used protecting group
- removable with strong acid

- very hindered
TiPS or TIPS
- quite stable to acid

3 Chemistry 335 Supplemental Slides: Protective Groups in Organic Chemistry

Protective Groups for Alcohols
2. Other protective groups for alcohols
group abbreviation addition structure removal

H2
benzyl Bn
Pd / C

H2, Pd/C
p-methoxybenzyl PMB or
DDQ

LiOH or NaOH
acetyl Ac
or KOH

LiOH or NaOH
benzoyl Bz
or KOH

methoxymethyl MOM H3O

4 Chemistry 335 Supplemental Slides: Protective Groups in Organic Chemistry

Protective Groups for Amines
1. Carbamates

protective group abbreviation removal

CBZ H2, Pd/C

H
BOC
or D

FMOC 2º amine base

5 Chemistry 335 Supplemental Slides: Protective Groups in Organic Chemistry

Protective Groups for Amines
2. Other protective groups for amines
group abbreviation addition structure removal

benzyl Bn H2, Pd/C

phthalimide Pth H2N-NH2

acetamide Ac H3O

benzamide Bz H3O

6 Chemistry 335 Supplemental Slides: Protective Groups in Organic Chemistry