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Aldehydes and Ketones

carbonyl group an aldehyde a ketone

Naming aldehydes and ketones

Common names:Common

names:Ketones and phenonesKetones and phenones 16-1

IUPAC Names

• IUPAC nomenclature treats aldehydes as derivatives of alkanes. The ending e is replaced byal

An alkane becomes an alkanal

Aldehydes:

e is replaced by al An alkane becomes an alkanal

• The aldehyde carbon is numbered C1 and does not have to be specified.• When -CHO is attached to a ring the compound is called carbaldehyde.

16-2

IUPAC Names

- Ketones are named by replacing the terminal - eof the corresponding alkane name with -one.Th b l b i i d th l t ibl b

Ketones:

Th e car b ony l car b on i s ass i gne d th e l owes t poss ible num b er. - carbonyl has higher priority than -OH, C=C, and CŁC. 16-3

Naming the Carbonyl Compounds- When functional group of higher ranking than carbonyl is present, the doubly

bonded oxygen is considered a substituent and the prefix oxo- is used (aldehyde has higher ranking than ketone).Od f d ff ti lO r d er o f prece d ence o f f unc ti ona l groups 16-4 Reviewing IR Characteristics of Aldehydes & Ketones aldehyde C H aldehyde C H (2820 & 2720 cm -1 16-5 Reviewing NMR Characteristics of Aldehydes & Ketones 1

Similar to alkenes the movement of the

electrons in the magnetic field 16-6 1

Similar

to alkenes the movement of the electrons in the magnetic field strengthens the external field;

2. The partially positive carbonyl carbon causes additional deshielding.

Preparation of Aldehydes

DCC / DMSO, H

3 PO 4 (Pfitzner-Moffatt reagent)

1. OsO

4 , NMO

2. HIO

4 or Pb(OAc) 4 16-7

Preparation of Ketones

Oxidation of 2

o alcohols: K 2 Cr 2 O 7 or CrO 3 / H 2 SO 4 , PCC

1. OsO

4 , NMO

2. HIO

4 or Pb(OAc) 4 (or Ac 2 O) 16-8

Preparations of Aldehydes and Ketones

(poisoned Pd catalyst) H 2 / Pd-BaSO 4 RCHO

LiAlH(OBu-t)

3 R C H O (deactivated LiAlH 4 RCClO R C H O

1. R'MgX

2. H 2

ORCR'O

NaC CR'

RCCCR'

O R' 2 CuLi R C R O R C R RCOOH

R'LiRCOO

Li

R'LiCR

OLi OLi CROH OH H 2 O - H 2

ORCR'O

R R RCOOH

R'MgXRCOO-MgX

16-9

Selective Oxidation of Allyl and Benzyl C-H

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