I) a) A compound ‘A’ of molecular formula
undergoes a series of reactions as shown below. Write the structures of A, B, C and D in the following reactions.
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b) Distinguish between the following:
i)
and ![]()
ii) Benzoic acid and methyl benzoate
c) Write the structure of 2-methylbutanal.
II) a) Write the structures of the main products when acetone
) reacts with the following reagents:
i) Zn- Hg/conc HCl
ii) ![]()
iii) ![]()
b) Arrange the following in the increasing order of their boiling points:
,
, ![]()
c) Give a simple chemical test to distinguish between the following pair of compounds:
and ![]()
I) a) Compound A is acetyl chloride which on hydrogenolysis with hydrogen molecule and is catalysed by Palladium on barium sulphate forms ethanal
(Compound B). Ethanal on reaction with dilute NaOH in aldol condensation to form compound C which is 3-hydroxy butanal (
). This compound C on heating form but-2-enal -
(Compound D).

b) (i) On heating both compounds with NaOH and I2,
forms yellow ppt of
whereas
does not.
(ii) Benzoic acid produces effervescence with
solution while ethyl benzoate does not. Benzoic acid produces vapours of benzene when heated with soda lime
while ethyl benzoate does not.
c)

II) a) (i) Acetone reduces to propane in the presence of zinc amalgam and conc. HCl to give propane. This reaction is called as Clemmensen reduction.
![]()
ii) Acetone reacts with semicarbazide to form semicarbazone.

iii) Acetone reduces to form tertiary alcohol in the presence of Grignard reagent.

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