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 _________
(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 _________
Show Hint
Ethers are neutral compounds that do not react with acids, bases, or 2,4-DNP, and aromatic ethers retain their structure upon hydrogenation of the benzene ring.
Correct Answer: 2
Approach Solution - 1
Analysis of the Given Conditions:
The given conditions indicate the compound must satisfy the following:
- Not dissolve in NaOH or HCl, which means it is a neutral compound, such as an ether.
- Not give an orange precipitate with 2,4-DNP, meaning it is not a carbonyl compound (aldehyde or ketone).
- On hydrogenation, give an identical compound, implying it has an unsaturated bond (e.g., an aromatic ring) that does not change the functional group upon reduction.
For the molecular formula C9H10O, possible isomeric structures satisfying the above conditions are:
- p-Methoxy toluene (C6H4(OCH3)CH3): The methoxy group is attached to the aromatic ring in the para position.
- o-Methoxy toluene (C6H4(OCH3)CH3): The methoxy group is attached to the aromatic ring in the ortho position.
These compounds are ethers, do not react with NaOH, HCl, or 2,4-DNP, and remain the same upon hydrogenation.
Conclusion: The number of isomeric compounds is 2.
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.
Top JEE Main Chemistry Questions
What will be the equilibrium constant of the given reaction carried out in a \(5 \,L\) vessel and having equilibrium amounts of \(A_2\) and \(A\) as \(0.5\) mole and \(2 \times 10^{-6}\) mole respectively?
The reaction : \(A_2 \rightleftharpoons 2A\)- At equilibrium the concentrations of and in a sealed vessel at . What will be for the reaction
- Find out the major products from the following reactions
Cobalt chloride when dissolved in water forms pink colored complex $X$ which has octahedral geometry. This solution on treating with cone $HCl$ forms deep blue complex, $\underline{Y}$ which has a $\underline{Z}$ geometry $X, Y$ and $Z$, respectively, are
- The correct order of atomic radii is:
Top JEE Main Chemical Reactions of Aldehydes Ketones and Carboxylic Acids Questions
- The major product formed in the following reaction is-
- In the following reactions, find the product A and B
Arrange the following in decreasing acidicstrength
- $CH_3 - CH_2 - CN \xrightarrow[\text{Ether}]{CH_3MgBr} A \xrightarrow{H_3O^+} B \xrightarrow[HCl]{Zn - Hg} C$ The correct structure of $C$ is
In a reaction,
reagents ' X ' and ' Y ' respectively are :
Top JEE Main Questions
- Two masses $m$ and $\frac{m}{2}$ are connected at the two ends of a massless rigid rod of length $l$. The rod is suspended by a thin wire of torsional constant $k$ at the centre of mass of the rod-mass system(see figure). Because of torsional constant $k$, the restoring torque is $\tau =k\theta$ for angular displacement $\theta$. If the rod is rota ted by $\theta_0$ and released, the tension in it when it passes through its mean position will be:
What will be the equilibrium constant of the given reaction carried out in a \(5 \,L\) vessel and having equilibrium amounts of \(A_2\) and \(A\) as \(0.5\) mole and \(2 \times 10^{-6}\) mole respectively?
The reaction : \(A_2 \rightleftharpoons 2A\)- The value of is
- The number of terms of an is even. The sum of the odd terms is and of the even terms is . The last term exceeds the first by . Then the number of terms in the series is ______.
A black body is at a temperature of 2880 K. The energy of radiation emitted by this body with wavelength between 499 nm and 500 nm is U1, between 999 nm and 1000 nm is U2 and between 1499 nm and 1500 nm is U3. The Wien's constant, b = 2.88×106 nm-K. Then,
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.