REACTION OF ALDEHYDES & KETONES-2

BY
AJAY KUMAR
Step-5:
Here Enolate Ion(4) loses a hydroxide ion.
 Retro-Aldol Condensation
A reaction in which a β-hydroxy carbonyl compound
decomposes into an aldehyde or ketone, plus another
carbonyl compound. ... This β-hydroxy ketone can be
decomposed back into acetone and acetophenone in a base-
catalyzed (or acid-catalyzed) retro-aldol reaction
Mechanism;
 Aldol & Retro-Aldol Condensation;

1 11

2.
 LDA(lithium Di-isopropylamide)
Important things about LDA:
(i) Strong base but poor nucleophile (too sterically
hindered)
(ii) LDA is very good for making enolates of esters,
aldehydes and ketones since it can give essentially 100%
(quantitative conversion) to the enolate
(iii) This allows the enolate to be alkylated or acylated
with less chance of self-condensation reactions.
 Q-1 Number of aldol products in the given
reaction is

(a) One (b) Two

(c) Three (d) Four

solution;---b
 Q-2What is the product (A) of following
reaction.

(a) (b)

(c) (d)
Ans-2,----b
 Q-3* In the following reaction

HCHO is a hydride donor while another RCHO is a

hydride acceptor:
(a)It is called crossed redox reaction (Cannizzaro).
(b) It is a disproportionation reaction.
(c) Nucleophilic addition reactivity is highest for
HCHO hence, it is always oxidised at the expense of
other aldehyde (with non–enolisable property).
(d) All of the above statements are correct.
Ans-(a, c) It is not a disproportionation reaction since the same compound
is not oxidised as well as reduced
Q-4* Consider following reaction

This :
(a) is a crossed Cannizzaro reaction.
(b) is intramolecular Cannizzaro reaction.
(c) causes substitution of H– by OH– in one–CHO
group and thus is oxidised while second
–CHO undergoes an addition of H– and is thus
reduced to alcohol.
(d) resembles aldol type condensation reaction.
THANK YOU