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Chapter 4: Problem 194

Which of the following reactions will give benzyl chloride? (a) \(\mathrm{C}_{6} \mathrm{H}_{6}+\mathrm{HCHO}+\mathrm{HCl} \stackrel{\mathrm{ZnCl}_{3}}{\longrightarrow}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}_{3}+\mathrm{Cl}_{2} \stackrel{\mathrm{hv}}{\Delta}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}_{3}+\mathrm{SO}_{2} \mathrm{Cl}_{2} \stackrel{\text { peroxide }}{\longrightarrow}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}_{3}+\mathrm{SOCl}_{2} \rightarrow\)

Short Answer

Expert verified
Answer: Reaction (c) will produce benzyl chloride as a product.

Step by step solution

01

Analyze Reaction (a)

In this reaction, we have benzene (\(\mathrm{C}_{6} \mathrm{H}_{6}\)), formaldehyde (\(\mathrm{HCHO}\)), and hydrochloric acid (\(\mathrm{HCl}\)) reacting together in the presence of a catalyst, zinc chloride (\(\mathrm{ZnCl}_{3}\)). The reaction produces a benzal chloride. Notice that benzal chloride's chemical formula is \(\mathrm{C}_{6} \mathrm{H}_{5}\mathrm{CHO}\mathrm{Cl}\), which is different from the desired product, benzyl chloride. Therefore, this reaction will not produce benzyl chloride.
02

Analyze Reaction (b)

In this reaction, we have toluene (\(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}_{3}\)) and chlorine (\(\mathrm{Cl}_{2}\)) reacting together under the influence of light or heat (represented by \(\mathrm{hv}\Delta\)). This reaction is a free radical halogenation, resulting in the chlorination of toluene. However, this reaction mainly generates ortho- and para-chlorotoluene and not benzyl chloride. Therefore, this reaction will not produce benzyl chloride.
03

Analyze Reaction (c)

In this reaction, we have toluene (\(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}_{3}\)), sulfur dioxide dichloride (\(\mathrm{SO}_{2}\mathrm{Cl}_{2}\)), and peroxide as the reaction components. This reaction is a radical halogenation with the presence of peroxide, resulting in the formation of benzyl chloride (\(\mathrm{C}_{6} \mathrm{H}_{5}\mathrm{CH}_{2}\mathrm{Cl}\)) as the main product. Thus, this reaction will produce benzyl chloride.
04

Analyze Reaction (d)

In this reaction, we have toluene (\(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}_{3}\)) and thionyl chloride (\(\mathrm{SOCl}_{2}\)) reacting together. This reaction leads to the formation of benzotrichloride (\(\mathrm{C}_{6} \mathrm{H}_{5}\mathrm{CCl}_{3}\)) rather than benzyl chloride. Therefore, this reaction will not produce benzyl chloride.
05

Identify the correct reaction

Based on the analysis of each reaction, we can conclude that Reaction (c) is the correct reaction that will produce benzyl chloride. All other reactions fail to produce the desired product, benzyl chloride.

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Most popular questions from this chapter

The major product of dehydration of hex-4-en-2-ol would be (a) 1,4 -hexadiene (b) 2,4 -hexadiene (c) 1,5 -hexadiene (d) 2,3 -hexadiene

The most useful reagent to distinguish ethanol from propan-1-ol is (a) \(\mathrm{HCl}\) and \(\mathrm{ZnCl}_{2}\) (b) \(\mathrm{I}_{2}\) and \(\mathrm{NaOH}\) (c) Cu at \(570 \mathrm{~K}\) (d) \(\mathrm{KMnO}_{4}\)

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 Fluorobenzene undergoes nucleophilic substitution much faster than chlorobenzene. and Statement 2 Eluorine being more electronegative causes more decrease in electron density at the carbon leading to a faster attack by the nucleophile.

Each question in this section has four suggested answers of which ONE OR MORE answers will be correct. Which of the following will give yellow precipitate when heated with powdered iodine and aqueous \(\mathrm{NaOH}\) ? (a) 2 -Butanol (b) 2-Methyl-2- propanol (c) 2-Pentanone (d) 3 -pentanol

Which of the following compounds will undergo hydrolysis most readily by \(\mathrm{S}_{\mathrm{N}} 1\) mechanism?
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