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Carbonyl Chemistry

Carbonyl Chemistry

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Published by: elgendy1204 on Dec 19, 2008
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1
Carbonyl Chemistry
(12 Lectures)
Aim of Course
To build upon elements of Dr E.H. Smith’s and Dr. D.C. Braddocks’s course.To introduce the chemistry of the carbonyl functional groups.
Course Objectives
At the end of this course you should be able to:Identify the various functional groups that involve carbonylsExplain reaction mechanisms associated with each type of functional group
Recommended Texts
Vollhardt, K.P.C. & Schore N.E. “Organic Chemistry” (2nd ed.)Clayden J., Greeves N., Warren S. & Wothers P. “Organic Chemistry”Sykes, P. “Mechanism in Organic Chemistry” (6th ed.)Warren, S. “Chemistry of the Carbonyl Group”Professor Donna G. Blackmondd.blackmond@imperial.ac.uktel. 41193 Room 639 C1
 
2
Aldehydes and Ketones
Aldehydes
Ketones
Carboxylic acids
R
C
H
O
Carboxylic acid derivatives:EstersAnhydridesAcid halidesAmidesWe begin our study of carbonyl compounds with the study of 
aldehydesaldehydes
and
ketonesketones
(the aldehyde/ketone oxidation level). –Carbonyl compounds are molecules containing the carbonyl group,
C=O
.These include:
R
C
R'
O
R
C
OH
O
R
C
OR'
O
O
C
R'
O
R
O
R
C
NH
2
O
R
C
X
O
Note: two bonds to heteroatoms
 
3
Nomenclature of Aldehydes and Ketones
Common names are used for the simplest aldehydes and ketones:
formaldehydebutyraldehydebenzaldehydeacetonebenzophenoneacetophenone
OCHH
OCHCH
2
CH
2
CH
3
OCCH
3
H
3
C
COH
COCH
3
CO
Common names are also used for carbonyl-containing substituent groups,which are known collectively as
acyl 
groups:
H CO
H
3
C CO
CO
formylacetylbenzoyl
4
Nomenclature of Aldehydes and Ketones
Traditional names are used for a great many aldehydes and ketones whichwere recognized as substances long before systems of nomenclature weredeveloped:
OH
OC HO
Three of the four bases which comprise DNA contain carbonyl groups (and allfour bases are nitrogen heterocycles, which we will discuss later):
NHNHOOH
3
C
NHNNHNONH
2
NNHNH
2
O
guanine (G)thymine (T) cytosine (C)cinnamaldehyde furfural acrolein
CH COHH
2
C
 
5
Structure of Aldehydes and Ketones
The carbonyl carbon of an aldehyde or ketone is sp
2
-hybridized.The bond angle is close to 120° (trigonal planar).The carbon-oxygen double bond consists of: –A
!
C-O bond –A
"
C=O bond
We can compare the C=O bond lengthto those of C=C double bonds
6
Properties of Aldehydes and Ketones
Aldehydes and ketones are polar molecules because the C=O bond has adipole moment:
CO
Their polarity makes aldehydes and ketones have higher boiling points thanalkenes of similar molecular weight.Aldehydes and ketones are not hydrogen bond donors (they can’t donate aproton); therefore, they have lower boiling points than alcohols of similar molecular weight.Aldehydes and ketones are hydrogen bond acceptors; this makes them haveconsiderable solubilities in water.
R
C
R'
O
HOHHOH
Ketones such as acetone are good solventsbecause they dissolve both aqueous and organiccompoundsRecall that acetone is a
 polar, aprotic 
solvent.
For acetone: dipole moment = 2.7 Dboiling piint = 56.5 ºC For propene:dipole moment = 0.4 Dboiling point = -47.4 ºFor i-propanol:dipole moment = 1.7 Dboiling point = 82.3 ºC 

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