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Chapter 16: Problem 76

Using your roadmaps as a guide, show how to convert (2-bromoethyl) benzene into 2-chloro-1-phenylethanone. Show all reagents and all molecules synthesized along the way.

Short Answer

Expert verified
Answer: The reagents required for this conversion are Sodium Chloride (NaCl), Chromic Acid (H2CrO4), and Sodium Hydroxide (NaOH). The products formed during this process are (2-Chloroethyl)benzene, Sodium Bromide (NaBr), 2-Chloro-1-phenylethanone, Sodium Chromate (NaCrO4), and Water (H2O).

Step by step solution

01

Substitution of Bromine with Chlorine

To convert (2-bromoethyl) benzene to 2-chloroethylbenzene, we will carry out a nucleophilic substitution reaction using Sodium Chloride (NaCl) as our nucleophile. The reaction can be represented as follows: (2-Bromoethyl)benzene + NaCl ⟶ (2-Chloroethyl)benzene + NaBr
02

Oxidation of 2-Chloroethylbenzene to 2-Chloro-1-phenylethanone

In order to convert 2-chloroethylbenzene into 2-chloro-1-phenylethanone, we need to oxidize the ethyl group to a carbonyl group. This can be achieved using the oxidizing agent chromic acid (H2CrO4) in the presence of a base such as sodium hydroxide (NaOH). The reaction can be represented as follows: (2-Chloroethyl)benzene + H2CrO4 + NaOH ⟶ 2-Chloro-1-phenylethanone + NaCrO4 + H2O In conclusion, we have successfully converted (2-bromoethyl) benzen
03

Reagents and molecules synthesized

The necessary reagents for this conversion are: 1. Sodium Chloride (NaCl) - for the nucleophilic substitution reaction 2. Chromic Acid (H2CrO4) - an oxidizing agent to oxidize the ethyl group 3. Sodium Hydroxide (NaOH) - a base to facilitate the oxidation The molecules synthesized during this process are: 1. (2-Chloroethyl)benzene - the intermediate product formed after the nucleophilic substitution reaction 2. Sodium Bromide (NaBr) - a byproduct of the nucleophilic substitution reaction 3. 2-Chloro-1-phenylethanone - the final product 4. Sodium Chromate (NaCrO4) - a byproduct of the oxidation reaction 5. Water (H2O) - a byproduct of the oxidation reaction

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Most popular questions from this chapter

The Wittig reaction can be used for the synthesis of conjugated dienes, as for example, 1-phenyl-1,3-pentadiene.

Draw a structural formula for the product formed by treating butanal with each reagent. (a) \(\mathrm{LiAlH}_{4}\) followed by \(\mathrm{H}_{2} \mathrm{O}\) (b) \(\mathrm{NaBH}_{4}\) in \(\mathrm{CH}_{3} \mathrm{OH} / \mathrm{H}_{2} \mathrm{O}\) (c) \(\mathrm{H}_{2} / \mathrm{Pt}\) (d) \(\mathrm{Ag}\left(\mathrm{NH}_{3}\right)_{2}{ }^{+}\)in \(\mathrm{NH}_{3} / \mathrm{H}_{2} \mathrm{O}\) (e) \(\mathrm{H}_{2} \mathrm{CrO}_{4}\), heat (f) \(\mathrm{HOCH}_{2} \mathrm{CH}_{2} \mathrm{OH}, \mathrm{HCl}\) (g) \(\mathrm{Zn}(\mathrm{Hg}) / \mathrm{HCl}\) (h) \(\mathrm{N}_{2} \mathrm{H}_{4}, \mathrm{KOH}\) at \(250^{\circ} \mathrm{C}\) (i) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}\) (j) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NHNH}_{2}\)

In dilute aqueous base, \((R)\)-glyceraldehyde is converted into an equilibrium mixture of \((R, S)\)-glyceraldehyde and dihydroxyacetone. Propose a mechanism for this isomerization.

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Starting with cyclohexanone, show how to prepare these compounds. In addition to the given starting material, use any other organic or inorganic reagents as necessary. (a) Cyclohexanol (b) Cyclohexene (c) cis-1,2-Cyclohexanediol (d) 1-Methylcyclohexanol (e) 1-Methylcyclohexene (f) 1-Phenylcyclohexanol (g) 1-Phenylcyclohexene (h) Cyclohexene oxide (i) trans-1,2-Cyclohexanediol
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