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Water is the only substance found naturally in all three states on Earth's surface.
Predict the correct intermediate and product in the following reaction: H 3 C ā C ā” C H ā H g S O 4 H 2 O , H 2 S O 4 H_3C-C \equiv CH \xrightarrow[HgSO_4]{H_2O, H_2SO_4} H 3 ā C ā C ā” C H H 2 ā O , H 2 ā S O 4 ā H g S O 4 ā ā Intermediate A ā A \rightarrow A ā Product B B B
hard
Hydrocarbons
2017
chemistry
Explanation To solve this problem, we need to understand the reaction mechanism of the hydration of alkynes. \\
The reaction given is: H 3 C ā C ā” C H ā H g S O 4 H 2 O , H 2 S O 4 H_3C-C \equiv CH \xrightarrow[HgSO_4]{H_2O, H_2SO_4} H 3 ā C ā C ā” C H H 2 ā O , H 2 ā S O 4 ā H g S O 4 ā ā
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Intermediate
Product
This is an example of the hydration of an alkyne, specifically acetylene, in the presence of
mercury(II) sulfate and sulfuric acid, which leads to the formation of a ketone.
Step-by-step mechanism:
1. Formation of the enol (Intermediate A):
ā¢ The alkyne reacts with water in the presence of
and
H 2 S O 4 . H_2SO_4. \\
H 2 ā S O 4 ā . ā¢ This leads to the formation of an enol, which is an alcohol with a double bond.
ā¢ The enol formed is unstable and quickly tautomerizes to a ketone.
2. Tautomerization to form the ketone (Product B):
ā¢ The enol undergoes keto-enol tautomerism, where the hydroxyl group (OH) and the double bond
rearrange to form a carbonyl group (C=O).
ā¢ This results in the formation of acetone, a ketone.
Analyzing the options:
ā¢ Option 1: The intermediate is an enol, but the product is incorrect.
ā¢ Option 2: The intermediate is a ketone, which is incorrect.
ā¢ Option 3: The intermediate is an enol, and the product is a ketone (acetone). This is correct.
ā¢ Option 4: The intermediate is incorrect.
Therefore, the correct option is Option 3.
Intermediate A:
H 3 C ā C ( O H ) = C H 2 H_3C-C(OH)=CH_2 \\
H 3 ā C ā C ( O H ) = C H 2 ā Product B:
H 3 C ā C ( = O ) ā C H 3 H_3C-C(=O)-CH_3 \\
H 3 ā C ā C ( = O ) ā C H 3 ā 
