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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. 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

Bond with MnOBond

with MnO 2 not oxidized (not allylic alcohol) CH 3 CHO CH 2 OH CHO MnO 2 , CHCl 3 , r.t. C H 2 O H fresh MnO 2 C H O C H 2 O H CH 2 CH 3 C H O C O 16-10

Description of a Carbonyl Group

not a hydroxy group carbonyl oxygencarbonyl oxygen basic site: proton adds here carbonyl carbon 16-11 electrophilic site: nucleophiles attack here

Nucleophilic Addition Reactions

HʊA

Basic conditions

Hth bl

Addition reaction: the elements of “Nu

H" have been

H ere th e car b ony l serves as an electrophile.

Addition

reaction: the elements of

“Nu

H" have been addedacross the carbonyl double bond.

Acidic conditions

Th b l b t d i t

16-12 Th e car b ony l can b e conver t e d i n t o a more powerful electrophile by protonatingthe carbonyl oxygen.

Generalization of Nucleophilic Addition to

Aldehydes and KetonesAldehydes

and

Ketones

16-13 Ketones are less reactive than aldehydes for both steric and electronic reasons.

Nucleophilic Addition of Water: Hydration

Aromatic aldehydes are less reactiveAromatic

aldehydes are less reactive than aliphatic aldehydes due to delocalization of the positive charge. 16-14 Nucleophilic Addition of HCN: Cyanohydrin Formation HCN is an exception: equilibrium favors cyanohydrin formation (88%) 16-15

Nucleophilic Addition of Grignard Reagent and

Hydride: Alcohol FormationHydride:

Alcohol

Formation

H 2 O or LiAlH 4 4 16-16

Nucleophilic Addition of Grignard Reagent

il b l a spec i a l car b ony l sodium acetylide 16-17

For making carboxylic acid

Stereoselectivity of Nucleophilic Addition to

Carbonyl Group: Cram

s Rule

Carbonyl

Group:

Cram s

Rule O H H P h CH 2 CH 3 + R'MgX H Et O Mg X RMg H Et OH H R H 3 O H Et OH H R major minor P h L S M OH Nu L S M OH NuM Ph H R X L O S O NuH Ph H R Ph H R

R = 35

o C CH 3

2.5 : 1

C 6 H 5 > 4 : 1 L H L H L S H 6 5 i-Pr 5 : 1 t-Bu 49 : 1R = -70 o C CH 3

5.6 : 1

t-Bu 499 : 1 L SM OR Nu 16-18 R

Imine and Enamine Formation

1 0 amine 2 0 amine 2 0quotesdbs_dbs17.pdfusesText_23