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Magazine Chapter 18: Q52P (page 970)
Show how you would synthesize the following derivatives from appropriate carbonyl compounds
Short Answer
a.
b.
c.
d.
e.
f.
Step by step solution
Oxime
A compound containing C=N-OH group, formed by the reaction of a ketone or an aldehyde with hydroxylamine is known as oxime.
Acetal
It is a derivative of an aldehyde or a ketone having two alkoxy groups in place of the carbonyl group.
Imine
Ammonia or primary amine under proper conditions reacts with a ketone or an aldehyde to form an imine.
Synthetic methodology
(a) Cyclopropanone reacts with hydroxylamine in presence of an acidic catalyst to give the product as cyclopropanone oxime.
reaction a
(b) Benzaldehyde reacts with cyclohexanamine cyclohexanone in presence of an acidic catalyst to give the product as (E)-N-benzylidenecyclohexanamine
reaction b
(c) Phenylmethanamine reacts with cyclohexanone in presence of an acidic catalyst to give the product as N-cyclohexylidene-1-phenylmethanamine.
reaction c
(d) 1H-inden-2(3H)-one reacts with ethane-1,2-diol in presence of an acidic catalyst to give the product as 1',3'-dihydrospiro[[1,3]dioxolane-2,2'-indene].
reaction d
(e) Cyclopentanamine reacts with propan-2-one in presence of an acidic catalyst to give the product as N-(propan-2-ylidene)cyclopentanamine.
reaction e
(f) Cyclohexanone reacts with methanol in presence of an acidic catalyst to give the product as 1,1-dimethoxycyclohexane.
reaction f
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