Number of isomeric compounds with molecular formula $C _9 H _{10} O$ which (i) do not dissolve in $NaOH$ (ii) do not dissolve in $HCl$ (iii) do not give orange precipitate with 2,4-DNP (iv) on hydrogenation give identical compound with molecular formula $C _9 H _{12} O$ is _________
Correct Answer: 2
Approach Solution - 1
As per the language of given question, the best possible isomeric structure is (cis and trans). So, the answer is .
Approach Solution -2
The only structure that satisfies all the given conditions is: C6H5-CH=CH-CH2-CH2-CH2-CH3
This structure is representative of a styrene molecule with a methyl group (CH3) at the end. It does not dissolve in NaOH or HCl, does not give an orange precipitate with 2,4-DNP, and upon hydrogenation, it forms ethylbenzene (C6H5-CH2-CH3), which has the molecular formula C9H12O.
\(\therefore\) the correct answer is '2', as there are two isomeric compounds that satisfy all the given conditions.
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Concepts Used:
Aldehydes, Ketones, and Carboxylic Acids
Aldehydes, Ketones, and Carboxylic Acids are carbonyl compounds that contain a carbon-oxygen double bond. These organic compounds are very important in the field of organic chemistry and also have many industrial applications.
Aldehydes:
Aldehydes are organic compounds that have the functional group -CHO.
Preparation of Aldehydes
Acid chlorides are reduced to aldehydes with hydrogen in the presence of palladium catalyst spread on barium sulfate.
Ketones:
Ketones are organic compounds that have the functional group C=O and the structure R-(C=O)-R’.
Preparation of Ketones
Acid chlorides on reaction with dialkyl cadmium produce ketones. Dialkyl cadmium themselves are prepared from Grignard reagents.
Carboxylic Acid:
Carboxylic acids are organic compounds that contain a (C=O)OH group attached to an R group (where R refers to the remaining part of the molecule).
Preparation of Carboxylic Acids
Primary alcohols are readily oxidized to carboxylic acids with common oxidizing agents such as potassium permanganate in neutral acidic or alkaline media or by potassium dichromate and chromium trioxide in acidic media.