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Show how you would synthesizefrom each compound. You may use any necessary reagents.

(a) heptanal

(b)oct - 1 - yne

(c) 2,3 - dimethylnon - 2 - ene

(d)octan - 2 - ol

(e) heptanoic acid

(f) CH3(CH2)5CN

Short Answer

Expert verified

The structure for octan - 2 - oneis shown below

octan - 2 - one

Step by step solution

01

Octan-2-one

The structure for octan - 2 - oneis shown below

octan - 2 - one

02

Synthetic methodology

(a) Heptanal on treatment with a Grignard reagent ( methylmagnesium bromide) and H3O+ gives octan - 2 - ol which on further reaction with PCC (pyridinium chlorochromate) oxidizes the secondary alcohol to ketone. The final product formed isoctan - 2 - one

reactiona

(b) Oxyemercuration ofoct - 1 - yne (alkene) takes place withHgSO4 andH2O to give the product as octan - 2 - one (ketone).

reactionb

(c) Ozone cleaves the double bonds similar to permanganate to give ketones and aldehydes. 2,3 - dimethylnon - 2 - eneundergoes ozonolysis to give the products as octan - 2 - oneand propan - 2 - one.

reactionc

(d) octan - 2 - olwhich reaction with PCC (pyridinium chlorochromate) oxidizes the secondary alcohol to ketone. The final product formed is octan - 2 - one

reactiond

(e) Heptanoic acid on treatment with an organlithium reagent ( methyllithium) and then H3O+gives octan - 2 - one.

reactione

(f) Heptanenitrile on treatment with a Grignard reagent ( methylmagnesium bromide) and H3O+gives octan - 2 - one .

reactionf

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