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During an experimental workup procedure,...

During an experimental workup procedure, a chemist treated a starting material with NaoH in the solvent acetone `[(CH_(3))_(2)C=O]`, however, the starting material was recovered unreacted. Instead, the chemist isolated a small amount of product A (shown below).
Product A
1. Elemental analysis of product A indicated that it consisted only of carbon, hydrogen, and oxygen.
2. Product A had a molecular weight of 116 g/mol.
3. Product A was a methyl ketone because it gave a positive iodoform test.
4. When product A was treated with `Br_(2)` in `C Cl_(4)`, the red bromine colour persisted, because no carbon-carbon double bonds were present to react with the bromine.
The structure of product A was further confirmed when treatment with hot sulfuric acid resulted in the corresponding dehydration product, product (B)gt
Q. Wihch of the following compounds from the passage will give a positive iodoform test.?

A

Product A only

B

Product A and product B

C

Product A and acetone only

D

Product A, product B, and acetone.

Text Solution

Verified by Experts

The correct Answer is:
D
.
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During an experimental workup procedure, a chemist treated a starting material with NaoH in the solvent acetone [(CH_(3))_(2)C=O] , however, the starting material was recovered unreacted. Instead, the chemist isolated a small amount of product A (shown below). Product A 1. Elemental analysis of product A indicated that it consisted only of carbon, hydrogen, and oxygen. 2. Product A had a molecular weight of 116 g/mol. 3. Product A was a methyl ketone because it gave a positive iodoform test. 4. When product A was treated with Br_(2) in C Cl_(4) , the red bromine colour persisted, because no carbon-carbon double bonds were present to react with the bromine. The structure of product A was further confirmed when treatment with hot sulfuric acid resulted in the corresponding dehydration product, product (B)gt Q. What is the molecular weight of a compound that undergoes an aldol self-condensation reaction to result in a beta -hydroxy ketone with a molecular weight of 144?

During an experimental workup procedure, a chemist treated a starting material with NaoH in the solvent acetone [(CH_(3))_(2)C=O] , however, the starting material was recovered unreacted. Instead, the chemist isolated a small amount of product A (shown below). Product A 1. Elemental analysis of product A indicated that it consisted only of carbon, hydrogen, and oxygen. 2. Product A had a molecular weight of 116 g/mol. 3. Product A was a methyl ketone because it gave a positive iodoform test. 4. When product A was treated with Br_(2) in C Cl_(4) , the red bromine colour persisted, because no carbon-carbon double bonds were present to react with the bromine. The structure of product A was further confirmed when treatment with hot sulfuric acid resulted in the corresponding dehydration product, product (B)gt Q. Based only on observation 1 and 2, which of the following compounds could have been product A?

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