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A carbonyl compound with molecular mass ...

A carbonyl compound with molecular mass 86, does not reduce Fehling's solution but forms crystalline bisulphite derivative and gives iodoform test. The possible compound is

A

2-pentanone and 3- pentanone

B

2-pentanone and 3-methyl-2-butanone

C

2-pentanone and pentanal

D

3-pentanone and 3-methyl-2-butanone.

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem, let's break it down step by step: ### Step 1: Analyze the Molecular Mass The molecular mass of the carbonyl compound is given as 86 g/mol. This information helps us narrow down the possible carbonyl compounds. **Hint:** Look for carbonyl compounds (aldehydes or ketones) that have a molecular mass close to 86 g/mol. ### Step 2: Identify the Type of Carbonyl Compound The problem states that the compound does not reduce Fehling's solution. This indicates that the compound is not an aldehyde, as aldehydes typically reduce Fehling's solution. Therefore, we can conclude that the compound is a ketone. **Hint:** Remember that only aldehydes can reduce Fehling's solution, while ketones do not. ### Step 3: Consider the Formation of Crystalline Bisulphite Derivative The compound forms a crystalline bisulphite derivative. This property is characteristic of carbonyl compounds, particularly ketones, which can react with sodium bisulphite to form a solid derivative. **Hint:** Look for ketones that readily form bisulphite derivatives. ### Step 4: Iodoform Test The compound gives a positive iodoform test. This test is specific for methyl ketones or compounds that can be oxidized to methyl ketones. Therefore, the carbonyl compound must be a methyl ketone. **Hint:** Recall that the iodoform test is positive for methyl ketones (RCOCH3) and some secondary alcohols. ### Step 5: Identify Possible Compounds Now, we need to identify specific methyl ketones with a molecular mass of 86 g/mol. The two common methyl ketones that fit this description are: 1. 2-Pentanone (C5H10O) 2. 3-Methylbutan-2-one (C5H10O) Both of these compounds have a molecular mass of 86 g/mol and are methyl ketones. **Hint:** Check the molecular formulas of the identified compounds to confirm their molecular mass. ### Conclusion Based on the analysis, the possible compounds that fit the criteria are 2-pentanone and 3-methylbutan-2-one. **Final Answer:** The possible compound is 2-pentanone or 3-methylbutan-2-one.

To solve the problem, let's break it down step by step: ### Step 1: Analyze the Molecular Mass The molecular mass of the carbonyl compound is given as 86 g/mol. This information helps us narrow down the possible carbonyl compounds. **Hint:** Look for carbonyl compounds (aldehydes or ketones) that have a molecular mass close to 86 g/mol. ### Step 2: Identify the Type of Carbonyl Compound ...
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(a) Illustrate the following name reactions by giving example : (i) Cannizzaro's reaction (ii) Clemmensen reduction (b) An organic compound A contains 69.77 % carbon , 11.63 % hydrogen and rest oxygen . The molecular mass of the compound is 86. it does not reduce Tollen's reagent but forms an addition compound with sodium hydrogen sulphite and give positive iodoform test. On vigorous oxidation it gives ethanoic and propanoic acid. Derive the possible structure of compound A .