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Chapter 5: Problem 63

\(\mathrm{H}_{2} \mathrm{C}=\mathrm{CH}-\mathrm{C}^{\mathrm{O}} \sum_{\mathrm{H}}^{\mathrm{CH}_{3} \mathrm{OH}}{\mathrm{dryHCl}}(\mathrm{A}) \stackrel{\mathrm{dil.KMnO}_{4}}{\longrightarrow}(\mathrm{B}) \stackrel{\mathrm{dil} \cdot \mathrm{HCl}}{\longrightarrow}(\mathrm{C})\) The structure of (C) is (a) \(\mathrm{H}_{2} \mathrm{C}=\mathrm{CHCH}_{2} \mathrm{OH}\) (b) \(\mathrm{HOCH}_{2}-\mathrm{CHOH}-\mathrm{CHO}\) (c) \(\mathrm{OHC}-\mathrm{CH}_{2}-\mathrm{COOH}\) (d) \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{COOH}\)

Short Answer

Expert verified
Answer: The structure of compound (C) is \(\mathrm{HOCH}_{2}-\mathrm{CHOH}-\mathrm{CHO}\).

Step by step solution

01

Initial Compound (A)

The initial compound (A) has this formula: \(\mathrm{H}_{2}\mathrm{C}=\mathrm{CH}-\mathrm{C}^{\mathrm{O}}\). This indicates that it is an aldehyde.
02

Reduction of Aldehyde with Dry HCl

In this step, the aldehyde group in compound (A) gets reduced by dry HCl to form compound (B). The aldehyde group is transformed into an alcohol group. Thus, the structure of compound (B) becomes: \(\mathrm{H}_{2}\mathrm{C}=\mathrm{CH}-\mathrm{CH}_{2}\mathrm{OH}\).
03

Oxidation with Dilute KMnO4

Now, we need to oxidize compound (B) with dilute \(\mathrm{KMnO}_{4}\). In this reaction, the carbon-carbon double bond will be oxidized to form two alcohol groups, so our intermediate product would be: \(\mathrm{HOCH}_{2}-\mathrm{CHOH}-\mathrm{CH}_{2}\mathrm{OH}\).
04

Acidification with Dilute HCl

The final step involves acidification with dilute HCl. This will convert any alcohols adjacent to a carbonyl group into a ketone or an aldehyde. In our case, the intermediate product formed in Step 3 has an alcohol group adjacent to another alcohol group. Upon acidification, the terminal alcohol group gets oxidized to an aldehyde group: \(\mathrm{HOCH}_{2}-\mathrm{CHOH}-\mathrm{CHO}\).
05

Identify the Structure of Compound (C)

Now that we have the structure of the final product after the sequence of reactions, we can compare it to the given options: (a) \(\mathrm{H}_{2}\mathrm{C}=\mathrm{CHCH}_{2}\mathrm{OH}\) (b) \(\mathrm{HOCH}_{2}-\mathrm{CHOH}-\mathrm{CHO}\) (c) \(\mathrm{OHC}-\mathrm{CH}_{2}-\mathrm{COOH}\) (d) \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{COOH}\) Our final product is the same as option (b), \(\mathrm{HOCH}_{2}-\mathrm{CHOH}-\mathrm{CHO}\). Therefore, option (b) is the correct answer for the structure of compound (C).

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Most popular questions from this chapter

Directions: Each question contains Statement- 1 and Statement-2 and has the following choices (a), (b), (c) and (d), out of which ONLY ONE is correct. (a) Statement- 1 is True, Statement- 2 is True; Statement- 2 is a correct explanation for Statement- 1 (b) Statement- 1 is True, Statement- 2 is True; Statement- 2 is NOT a correct explanation for Statement-1 (c) Statement- 1 is True, Statement- 2 is False (d) Statement- 1 is False, Statement- 2 is True Statement 1 Eventhough carboxylic acids contain a \(>C=O\) group, they do not give the characteristic reaction of carbonyl compounds. and Statement 2 The electrophilicity of carbonyl carbon is less in carboxylic acids due to resonance.

The carboxylic acid(s) that form anhydride on heating with phosphorus pentoxide is/are (a) Malonic acid (b) Ethanoic acid (c) Maleic acid (d) Succinic acid

Directions: Each question contains Statement- 1 and Statement-2 and has the following choices (a), (b), (c) and (d), out of which ONLY ONE is correct. (a) Statement- 1 is True, Statement- 2 is True; Statement- 2 is a correct explanation for Statement- 1 (b) Statement- 1 is True, Statement- 2 is True; Statement- 2 is NOT a correct explanation for Statement-1 (c) Statement- 1 is True, Statement- 2 is False (d) Statement- 1 is False, Statement- 2 is True Statement 1 p-nitrophenol is more acidic than o - nitrophenol. and Statement 2 Steric effect due to the presence of \(-\mathrm{NO}_{2}\) group at ortho position of \(-\mathrm{OH}\) decreases the acidic strength of o-nitrophenol.

Which of the following reactions will give acetophenone as a product? (a) Acid catalysed hydration of styrene followed by oxidation with hot alkaline \(\mathrm{KMnO}_{4}\). (b) Phenyl acetylene \(\stackrel{\mathrm{d} \mathrm{H}, \mathrm{SO}_{4}^{\prime} \mathrm{H}_{\mathrm{E}}^{2+}}{\longrightarrow}\) Aldehydes, Ketones and Carboxylic Acids (c) Reaction of benzoyl chloride with dimethyl cadmium. (d) Dry distillation of a mixture of calcium acetate and calcium benzoate.

Which carbonyl compound among the following is most reactive towards nucleophilic addition? (a) CCC(=O)CC (b) CC(=O)CCl (c) CC(=O)CCCl (d)
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