y ALDEHYDES AND KETONES CHAPTER 12 - Cook...
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Survey of Organic Chemistry CHAPTER 12 ALDEHYDES AND KETONES CHEM 240: Fall 2019 Prof. Greg Cook cook.chem.ndsu.nodak.edu/chem240 1
Transcript of y ALDEHYDES AND KETONES CHAPTER 12 - Cook...
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Chem
istry
CHAPTER 12 ALDEHYDES AND KETONES
CHEM 240: Fall 2019
Prof. Greg Cook
cook.chem.ndsu.nodak.edu/chem240
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http://cook.chem.ndsu.nodak.edu/chem341
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Chem
istry
Carbonyl Compounds
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R H
O
R R'
O
ketonealdehyde
R OR'
O
ester
R OH
O
carboxylic acid
R X
O
acid halide
R SR'
O
thioester
R NH2
O
amide
R X
O
acid anhydride
R
O
HO OH
O
carbonic acid
H2N NH2
O
urea
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Chem
istry
Naming aldehydes and ketones
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H H
O
methanalformaldehyde
H3C H
O
ethanalacetaldehyde
H
O
benzaldehydebenzene carbaldehyde
2,4-pentanedioneacetylacetone
OO
H
O
propenalacrolein
H3C CH3
O
propanoneacetone
O
trans-hex-4-en-2-one
CH3
O
acetophenone
O
benzophenone
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Chem
istry
Carbonyl Substituents
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R
O
acyl group
H
O
formylH3C
O
acetyl
O
benzoyl
methyl 3-oxopentanoateOCH3
OO
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Chem
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Nature of the C=O bond
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O
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Chem
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Types of Nucleophiles
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Chem
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Addition of Grignard Reagents
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Chem
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Addition of Grignard Reagents
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Chem
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Types of Nucleophiles
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Chem
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Nature of the C=O bond
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O
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Chem
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Mechanism of hydration
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O
acetone acetonehydrate
HO OH+ H2O H H
O
formaldehydeH Hformaldehydehydrate
HO OH+ H2O
99.9%99.9%
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Chem
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General Activation - acid vs base
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O
Acid Catalyzed Hydration
HA OH
moreelectrophilic
H2OHO O
H
HA HO OH
acid activates the carbonyl making it more reactive (more electrophilic) so water can add
O H+ OH
carbonyl is more electrophilic
OH -OH
nucleophile is more reactive
Nuc H Nuc
Base Catalyzed Hydration
O OH O OH HO OH
hydroxide is a more reactive nucleophile than water and can add more readily to the carbonyl
H2O
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Chem
istry
Addition of Alcohols
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O
a hemiacetal
+ ROH2H+
HO OR
an acetal
RO OR
(+ ROH) (+ ROH)(- H2O)
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Chem
istry
Addition of Alcohols
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O
a hemiacetal
+ ROH2H+
HO OR
an acetal
RO OR
(+ ROH) (+ ROH)(- H2O)
O
HA
OH
OHR
O O HRH A O O R
H
Hemiacetal
-H2O
O RO R
resonance structures
HA
O O R
H
R
A
O O RR
OH
resonance structures
HO R
O O R
H
H
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Chem
istry
Addition of Alcohols
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O
HA
OH
OHR
O O HRH A O O R
H
Hemiacetal
-H2O
O RO R
resonance structures
HA
O O R
H
R
A
O O RR
OH
resonance structures
HO R
O O R
H
H
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Chem
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Acetals are important in sugars
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Chem
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Acetals are carbonyl protecting groups
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Chem
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Formation of Imines
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Chem
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Imines have important biological function
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Chem
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Reduction of imines
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Chem
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Keto-Enol Tautomerism
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Chem
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Racemization
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Chem
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Enols are nucleophilic
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Chem
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Oxidation of Aldehydes
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Chem
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Oxidation of Aldehydes
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Chem
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Reduction of Aldehydes and Ketones
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a carbonyl compound
C
OH
" "
an alcohol
CHO H
NaBH4
LiAlH4
