Aldehydes ketones and carboxylic acids Lecture-3
Physical properties
Methanal $(HCHO)$ is gas at room temprature, paraformaldehyde $[(HCHO)_n]$ is solid
Ethanal $CH_3CHO$ is a volatile liquid
The boiling points of aldehydes & ketones are higher than the hydrocarbon & either of similar molecular mass due to molecular interaction arising out of dipole-dipole interaction
The boiling points of aldehydes & ketons are lower than alcohols of similar molecular masses due to absence of hydrogen bonding
Mol-mass - 55-60
$CH_3CH_2CH_2OH > CH_3CH_2CHO≈CH_3C-CH_3 > CH_3OCH_2CH_3 > CH_3CH_2CH_2CH_3$
Lower aldehydes and ketones are soluble in water due to hydrogen bonding with water
As the size of substituent increases, the solubility decreases
Lower aldehydes have sharp pungent smell
The size increases, the smell becomes more fragnent
Nuclear addition reaction
Reactivity : Aldehydes are more reactive than ketones
Steric : Two alkyl groups increases the bulkiness around carbonyl carbon
Electronic effect : Two alkyl groups decreases the eletrophilicity of carbonyl due to (+I) effect
Aldehydes ketones and carboxylic acids Lecture-3 Nuclear addition reaction
Reactivity: acetaldehyde $>$ benzaldehyde
Electophilicity of carbonyl carbon gets reduced
(1) Hydrogen cyanide addition
Aldehydes ketones and carboxylic acids Lecture-3 Nuceophilic addition reaction
Examples:
(2) Addition of sodium hydrogen sulphite $(NaHSO_3)$
Nuceophilic addition reaction
(3) Addition of alcohols
Aldehydes react with one molecule of monohydric alcohol to provide monoalkoxy alcohol(hemiacetal)
Hemiacetal reacts further with molecule of monohydric alochol to generate dialkoxy compound (acetal)
Remove $H_2O$ by distillation using Dean-Stark or molecular sieve
(4) Addition of grignard reagent (R’MgX)
(5) Addition of ammonia & its derivatives
Reduction reaction
Clemenson reduction
Wolff-kishner reaction
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