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Chapter 5: Problem 146

The reagent that can be employed for the conversion \(\mathrm{H}_{2} \mathrm{C}=\mathrm{CH}-\mathrm{CH}_{2} \mathrm{OH} \rightarrow \mathrm{H}_{2} \mathrm{C}=\mathrm{CH}-\mathrm{CHO}\) is (a) acidified \(\mathrm{KMnO}_{4}\) (b) alkaline \(\mathrm{KMnO}_{4}\) (c) \(\mathrm{MnO}_{2}\) (d) \(\mathrm{Ag}_{2} \mathrm{O}\) moist

Short Answer

Expert verified
Answer: Alkaline \(\mathrm{KMnO}_{4}\) (option b).

Step by step solution

01

Analyze the effect of acidified \(\mathrm{KMnO}_{4}\) on the given compound

Acidified \(\mathrm{KMnO}_{4}\) is a strong oxidizing agent. It can oxidize alkenes to diols and alcohols to carboxylic acids. In our case, the starting compound has an alkene and alcohol in its structure. The acidified \(\mathrm{KMnO}_{4}\) would oxidize the alcohol to a carboxylic acid, producing a dicarboxylic acid instead of the desired aldehyde product. This rules out option (a).
02

Analyze the effect of alkaline \(\mathrm{KMnO}_{4}\) on the given compound

Alkaline \(\mathrm{KMnO}_{4}\) is a milder oxidizing agent than the acidified version. It is known to oxidize primary alcohols to aldehydes and then to carboxylic acids. However, it doesn't oxidize alkenes to diols. In the given compound, the alkene group remains unaffected, and the alcohol group will be oxidized to the aldehyde, forming the desired product, \(\mathrm{H}_{2}\mathrm{C}=\mathrm{CH}-\mathrm{CHO}\). Therefore, option (b) is the correct answer.
03

Analyze the effect of \(\mathrm{MnO}_{2}\) on the given compound

\(\mathrm{MnO}_{2}\) can act as a catalyst in some oxidation reactions, but it is not a strong enough oxidizing agent to convert the given alcohol group to an aldehyde in this case. Thus, option (c) is not suitable for this conversion.
04

Analyze the effect of \(\mathrm{Ag}_{2}\mathrm{O}\) moist on the given compound

Moist \(\mathrm{Ag}_{2}\mathrm{O}\) is a mild oxidizing agent, and it can oxidize aldehydes to carboxylic acids. However, it doesn't oxidize the alcohol group to an aldehyde in the given compound. Therefore, option (d) is not suitable for this conversion. Based on the analysis, the correct reagent for the conversion \(\mathrm{H}_{2}\mathrm{C}=\mathrm{CH}-\mathrm{CH}_{2}\mathrm{OH} \rightarrow \mathrm{H}_{2}\mathrm{C}=\mathrm{CH}-\mathrm{CHO}\) is alkaline \(\mathrm{KMnO}_{4}\) (option b).

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Most popular questions from this chapter

p-cresol \(\stackrel{\mathrm{CHCl}_{3} \mathrm{NaOH}}{\longrightarrow} \mathrm{A} \stackrel{\mathrm{HCN}}{\longrightarrow} \mathrm{B} \stackrel{\mathrm{H}, \mathrm{O}^{+}}{\longrightarrow} \mathrm{C}\) Which of the following statements is not true about the product (C) in the above sequence of reactions? (a) It gives violet colour with neutral ferric chloride solution. (b) It is optically active. (c) There are six \(\mathrm{sp}^{2}\) hybridised carbon atoms in one molecule of it. (d) It liberates \(\mathrm{CO}_{2}\) when treated with \(\mathrm{NaHCO}_{3}\) solution.

The product (P) formed in the following reaction is \(\mathrm{CH}_{3}-\mathrm{C}=\mathrm{CH} \frac{\text { (i) NaNH }_{2}}{\text { (ii) HCHo }}(\mathrm{P})\) (a) \(\mathrm{CH}_{3}-\mathrm{C} \equiv \mathrm{C}-\mathrm{CH}_{2} \mathrm{OH}\) (b) \(\mathrm{CH}_{3}-\mathrm{C}=\mathrm{C}-\mathrm{COONa}\) (c) \(\mathrm{CH}_{3}-\mathrm{C} \equiv \mathrm{C}-\mathrm{CHO}\) (d) \(\mathrm{CH}_{3}-\mathrm{CH}=\mathrm{CH}-\mathrm{CHO}\)

The organic compound formed by the dry distillation of calcium adipate is reduced with zinc amalgam and concentrated hydrochloric acid. The final product formed is (a) cyclopentane (b) pentane (c) cyclopentanol (d) cyclohexane

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 Acetals and ketals are unstable in aqueous acid conditions, but quite stable to alkaline conditions. and Statement 2 A weaker base like (OH) cannot displace a stronger base like (OR) found in acetals and ketals.

2 -phenyl ethanol on oxidation with alkaline \(\mathrm{KMnO}_{4}\) gives (a) benzaldehyde (b) 2 -phenyl ethanoic acid (c) benzoic acid (d) 2 -phenyl ethanol
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