Draw the product(s) of the following reactions. CH3CH2CH2-CEC-CH2CH2CH3 1. BHz / THE 2. H2O2 / aqueous NaO

Discipline: Chemistry

Type of Paper: Question-Answer

Academic Level: Undergrad. (yrs 3-4)

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Question

Draw the product(s) of the following reactions. CH3CH2CH2-CEC-CH2CH2CH3 1. BHz / THE 2. H2O2 / aqueous NaO

Draw the product(s) of the following reactions.
HO
C-CEC-CH3
H2
нс
Lindlar catalyst
In progress
Consider E/Z stereochemistry

Expert Answer

1. Reaction of BH3 in basic condition with alkyne is the water addition to the triple bond and forming unstable enol form which in turn tautomerize to the ketone or aldehyde for terminal triple bond. Addition of water to the triple bond follows anti-Mark's rule.

In our reaction, 4-octyne under go water addition and forms a single product, 4-octanone (P1) because it is a symmetrical alkyne. Refer the below image for reaction.

2. Reaction of H2 in Lindlar catalyst with alkyne is the H addition to the triple bond. The only product is Z alkene.

In our reaction, (S)-pent-3-yn-2-ol under go reduction reaction with H2 in Lindlar catalyst and forms the Z - isomer (P2), (S,Z)-pent-3-en-2-ol. Refer the below image for reaction.

$Сня сна сн,- Cac-cha снасна\n11. BH3/THE\nV2. H2O2lar Nash\nс на сно сну - c- сн - с насы, сыз\n(Р)\nно..\nc-c=C-C Hз\nне 1.\nLindla$