Number of isomeric compounds with molecular formula C9H10Owhich (i) do not dissolve in NaOH(ii) do not dissolve in HCI. (iii) do not give orange precipitate with 2,4-DNP (iv) on hydrogenation give identical compound with molecular formula C9H12O is __________.Correct answer is '2'. Can you explain this answer?

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Answer

2 possibilities

Answer

Number of isomeric compounds with molecular formula C9H10O:

To determine the number of isomeric compounds with the molecular formula C9H10O, we need to consider the different possible arrangements of atoms within the molecule.

i) Compounds that do not dissolve in NaOH:

When a compound does not dissolve in NaOH, it indicates the absence of an acidic hydrogen atom in the molecule. Compounds with a carbonyl group (C=O) typically dissolve in NaOH due to the formation of a salt through acid-base reaction.

ii) Compounds that do not dissolve in HCl:

When a compound does not dissolve in HCl, it suggests the absence of a basic functional group, such as an amine or an alcohol. These functional groups typically react with acid to form a salt.

iii) Compounds that do not give an orange precipitate with 2,4-DNP:

2,4-Dinitrophenylhydrazine (2,4-DNP) is a reagent commonly used to detect the presence of aldehydes and ketones. When an aldehyde or ketone reacts with 2,4-DNP, it forms an orange precipitate. Therefore, compounds that do not give an orange precipitate with 2,4-DNP are not aldehydes or ketones.

iv) Compounds that give an identical compound on hydrogenation:

Hydrogenation is a reaction that involves the addition of hydrogen (H2) to a molecule. If a compound gives an identical compound upon hydrogenation, it suggests that the compound contains a carbon-carbon double bond (C=C), which is converted to a single bond (C-C) during the reaction.

Combining the information:

Based on the given information, we can conclude that the compound should not contain an acidic hydrogen atom, a basic functional group, and should not be an aldehyde or ketone. Additionally, it should contain a carbon-carbon double bond.

Possible structures:

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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