Draw the structures of organic compounds A and B. Indicate stereochemistry where applicable.

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Draw the structures of organic compounds A and B. Indicate stereochemistry where applicable.

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Answer 1

Answer #1

Concepts and reason

This problem is based on the concept of alkynes.

Alkynes are the class of organic compounds containing carbon-carbon triple bonds. Alkyne is converted into higher alkyne on reaction with haloalkane in presence of a base. Reduction of alkyne to alkene can be done in the presence of Lindlar's catalyst.

Fundamentals

Alkynes that have a hydrogen attached to triple bonded carbon are termed as terminal alkynes. The other alkynes are referred as nonterminal alkynes or internal alkynes. Non-terminal alkynes are more stable and have more boiling point that the corresponding terminal alkynes.

(1)

The reaction of acetylene with propyl bromide in presence of sodamide is written as follows:

NaNH
+ CH3CH2CH2Br
H-CECH - →H-CEC Na -
→
H-CEC-CH2CH2CH3
Α
Lindlars catalyst
H—c5c-CH2CH2CH3
H
=-—CH2CH2CH3
HO, H307
CEC-CH

(2)

The reaction of pent-1-yne with Lindlar's catalyst is as follows:

H-CEC-CH2CH2CH3-
Lindlars catalyst
→
H-
=f-CH2CH2CH3

The alkene formed from above reaction gives alcohol on hydrolysis as follows:

н——
ОН
—
—сн,сн,сн,
Н,0, H,0*,

Ans: Part 1

The structure of organic compound A is as follows:

H-CEC-CH2CH2CH3

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Answer 2

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