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Magazine Chapter 9: Q9-4P (page 270)
What products would you obtain by hydration of the following alkynes?
Short Answer
Answer:
a.
b.
Step by step solution
Hydration of alkynes
Alkyne undergoes hydration in the presence of mercury(II) sulfate. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H attaches to the less highly substituted one.
Enol is an intermediate in the reaction, which rearranges into a ketone by a process called keto-enol tautomerism. The individual keto and enol forms are said to be tautomers.
Step2: Hydration of CH3CH2CH2C≡CCH2CH2CH3
The reaction occurs with Markovnikov regiochemistry.Enol is an intermediate in the reaction, which rearranges into a ketone by a process called keto-enol tautomerism
The symmetrical alkyne leads to the formation of the single product as shown:
Hydration of CH3CH(CH3)CH2C≡CCH2CH2CH3
The reaction occurs with Markovnikov regiochemistry.Enol is an intermediate in the reaction, which rearranges into a ketone by a process called keto-enol tautomerism
The unsymmetrical alkyne leads to the formation of the two products as shown:
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