Question
Hard
Solving time: 6 mins
An organic compound contains % carbon, % hydrogen and rest oxygen. The molecular mass of the compound is . It does not reduce Tollens reagent but forms an addition compound with sodium hydrogensulphite and give positive iodoform test. On vigorous oxidation, it gives ethanoic and propanoic acid. Write the possible structure of the compound.
Found 6 tutors discussing this question
Discuss this question LIVE
13 mins ago
Text solutionVerified
An organic compound contains carbon, hydrogen and rest oxygen. The molecular mass of the compound is .
Simple atomic ratio
The empirical formula is
Empirical formula mass . It is equal to molecular formula mass. Hence, molecular formula is same as empirical formula.
It does not reduce Tollens reagent. Hence, it is not an aldehyde
It forms an addition compound with sodium hydrogensulphite.
Hence, it contains carbonyl group.
It give positive iodoform test.
Hence, it is a methyl ketone
On vigorous oxidation it gives ethanoic and propanoic acid.
Hence, it is -pentanone.
Simple atomic ratio
The empirical formula is
Empirical formula mass . It is equal to molecular formula mass. Hence, molecular formula is same as empirical formula.
It does not reduce Tollens reagent. Hence, it is not an aldehyde
It forms an addition compound with sodium hydrogensulphite.
Hence, it contains carbonyl group.
It give positive iodoform test.
Hence, it is a methyl ketone
On vigorous oxidation it gives ethanoic and propanoic acid.
Hence, it is -pentanone.
Was this solution helpful?
54
Share
Report
Filo tutor solutions (6)
Learn from their 1-to-1 discussion with Filo tutors.
8 mins
Uploaded on: 10/2/2023
Was this solution helpful?
146
Share
Report
1 mins
Uploaded on: 1/21/2024
Was this solution helpful?
108
Share
Report
One destination to cover all your homework and assignment needs
Learn Practice Revision Succeed
Instant 1:1 help, 24x7
60, 000+ Expert tutors
Textbook solutions
Big idea maths, McGraw-Hill Education etc
Essay review
Get expert feedback on your essay
Schedule classes
High dosage tutoring from Dedicated 3 experts
Practice more questions from Chemistry Part-II (NCERT)
Q1
Give plausible explanation for each of the following:
(i) Cyclohexanone forms cyanohydrin in good yield but 2,2,6-trimethylcyclohexanone does not.
(ii) There are two groups in semicarbazide. However, only one is involved in the formation of semicarbazones.
(iii) During the preparation of esters from a carboxylic acid and an alcohol in the presence of an acid catalyst, the water or the ester should be removed as soon as it is formed.
(i) Cyclohexanone forms cyanohydrin in good yield but 2,2,6-trimethylcyclohexanone does not.
(ii) There are two groups in semicarbazide. However, only one is involved in the formation of semicarbazones.
(iii) During the preparation of esters from a carboxylic acid and an alcohol in the presence of an acid catalyst, the water or the ester should be removed as soon as it is formed.
Q2
An organic compound contains % carbon, % hydrogen and rest oxygen. The molecular mass of the compound is . It does not reduce Tollens reagent but forms an addition compound with sodium hydrogensulphite and give positive iodoform test. On vigorous oxidation, it gives ethanoic and propanoic acid. Write the possible structure of the compound.
Q3
Give names of the reagents to bring about the following transformations:
(i) Hexan-1-ol to hexanal
(ii) Cyclohexanol to cyclohexanone
(iii) -Fluorotoluene to
(iv) Ethanenitrile to ethanal
-fluorobenzaldehyde
(v) Allyl alcohol to propenal
(vi) But-2-ene to ethanal
View allPractice questions from Chemistry Part-II (NCERT)
Question 1
Easy
Views: 5,922
Question 2
Medium
Views: 6,395
(i) PropanonetoPropene
(ii) Benzoic acid to Benzaldehyde
(iii) Ethanol to 3-Hydroxybutanal
(iv) Benzene to m-Nitroacetophenone
(v) Benzaldehyde to Benzophenone €“
(vi) Bromobenzeneto 1-PhenylethanoL
(vii) Benzaldehyde to 3-Phenylpropan-1-ol.
(viii) Benzaldehyde to α Hydroxyphenylacetk acid
(ix) Benzoic acid to m-Nitrobenzy 1 alcohol
Question 3
Medium
Views: 5,889
Question 4
Medium
Views: 5,636
(i) the amide which gives propanamine by Hoffmann bromamide reaction.
(ii) the amine produced by the Hoffmann degradation of benzamide.
Practice more questions from Aldehydes, Ketones and Carboxylic Acids
Practice questions on similar concepts asked by Filo students
Question 1
Views: 5,832
Question 3
Views: 5,088
Question 4
Views: 5,938
Stuck on the question or explanation?
Connect with our Chemistry tutors online and get step by step solution of this question.
231 students are taking LIVE classes
Question Text | An organic compound contains % carbon, % hydrogen and rest oxygen. The molecular mass of the compound is . It does not reduce Tollens reagent but forms an addition compound with sodium hydrogensulphite and give positive iodoform test. On vigorous oxidation, it gives ethanoic and propanoic acid. Write the possible structure of the compound. |
Updated On | Jan 21, 2024 |
Topic | Aldehydes, Ketones and Carboxylic Acids |
Subject | Chemistry |
Class | Class 12 |
Answer Type | Text solution:1 Video solution: 6 |
Upvotes | 660 |
Avg. Video Duration | 6 min |