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Chapter 5: Problem 122

Write the steps involved in the following conversions? (a) Benzaldehyde to benzophenone (b) Benzaldehyde to 3 -phenylpropan-1-ol (c) Benzene to 2-phenyl ethanoic acid

Short Answer

Expert verified
Question: Provide an overview of the conversion of benzaldehyde to benzophenone. Answer: The conversion of benzaldehyde to benzophenone involves a Friedel-Crafts Acylation reaction. This reaction takes place between benzaldehyde and benzene in the presence of aluminum chloride (AlCl3) as a catalyst. The aldehyde functional group of benzaldehyde is converted to a ketone group with the addition of a benzene ring, resulting in the formation of benzophenone.

Step by step solution

01

Identify the functional groups in the starting and target compounds

Benzaldehyde contains an aldehyde functional group (-CHO), while benzophenone is a ketone containing a carbonyl group (C=O) bonded to two benzene rings. The goal here is to convert the aldehyde group into a ketone group with an additional benzene ring.
02

Perform a Friedel-Crafts Acylation

To achieve this conversion, we can use a Friedel-Crafts Acylation reaction. React benzaldehyde with a benzene molecule and aluminum chloride (AlCl3) as a catalyst. The aluminum chloride will activate the carbonyl group of benzaldehyde and generate electrophilic acylium ion, which then reacts with benzene to form benzophenone. The balanced reaction is: Benzaldehyde + Benzene + AlCl3 -> Benzophenone + HCl + AlCl3 This completes the conversion of benzaldehyde to benzophenone. (b) Benzaldehyde to 3-phenylpropan-1-ol
03

Identify the functional groups in the starting and target compounds

Benzaldehyde contains an aldehyde functional group (-CHO), while 3-phenylpropan-1-ol is an alcohol containing a hydroxyl group (-OH) and a phenyl group. The goal here is to convert the aldehyde group to a hydroxyl group with an additional CH2 group.
04

Perform a Grignard Reaction

To achieve this conversion, we can use a Grignard reaction. React benzaldehyde with phenylmagnesium bromide (PhMgBr) to form 3-phenylpropan-1-ol. The balanced reaction is: Benzaldehyde + PhMgBr -> 3-Phenylpropan-1-ol + MgBrOH This completes the conversion of benzaldehyde to 3-phenylpropan-1-ol. (c) Benzene to 2-phenyl ethanoic acid
05

Identify the functional groups in the starting and target compounds

Benzene contains a phenyl group, while 2-phenyl ethanoic acid is a carboxylic acid containing a carboxyl group (COOH) bonded to a phenyl group. The goal is to convert benzene to a carboxylic acid.
06

Perform a Friedel-Crafts Acylation

First, we can perform a Friedel-Crafts Acylation to convert benzene to an acetylbenzene. To do this, react benzene with acetyl chloride (CH3COCl) in the presence of aluminum chloride (AlCl3) as a catalyst. The balanced reaction is: Benzene + CH3COCl + AlCl3 -> Acetylbenzene + HCl + AlCl3
07

Perform a Clemmensen Reduction

Now, we have acetylbenzene. We can convert this compound to ethylbenzene via a Clemmensen reduction. React acetylbenzene with zinc amalgam (Zn(Hg)) and hydrochloric acid (HCl). The balanced reaction is: Acetylbenzene + Zn(Hg) + HCl -> Ethylbenzene + H2O + ZnCl2
08

Oxidize ethylbenzene to 2-phenyl ethanoic acid

Finally, we need to convert ethylbenzene to 2-phenyl ethanoic acid. This can be achieved through oxidation using potassium permanganate (KMnO4) as the oxidizing agent and aqueous sulfuric acid (H2SO4). The balanced reaction is: Ethylbenzene + KMnO4 + H2SO4 -> 2-Phenyl ethanoic acid + MnSO4 + KHSO4 + H2O This completes the conversion of benzene to 2-phenyl ethanoic acid.

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Most popular questions from this chapter

The products of oxidation of 2 -pentanone with concentrated nitric acid are (a) propanoic acid and ethanoic acid (b) butanoic acid and methanoic acid (c) propanoic acid and methanoic acid (d) 2 -methyl propanoic acid and methanoic acid

Identify the correct statements among the following. (a) Formaldehyde can react with both \(-\mathrm{NH}_{2}\) groups in semicarbazide. (b) In mixed Cannizzaro reaction involving HCHO, it is always the intermediate formed from HCHO which transfers its hydride to the other aldehyde. (c) Benzaldehyde reduces both Tollens' reagent and Fehling's solution. (d) In Fehling's solution, Cu(II) ions are kept in soluble form of a complex in alkaline medium.

Benzophenone does not react with (a) \(\mathrm{NaHSO}_{3}\) (b) \(\mathrm{H}_{2} \mathrm{NOH}\) (c) \(\mathrm{HCN}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{MgBr}\)

O=C1C=CCCC1 O=C1CCCCC1 (ii) \(\mathrm{H}_{3} \mathrm{O}^{+} /\). O=C1C=CCCC1=C1CCCCC1 (i)(X) The reagent (X) required is (a) \(\mathrm{NaOH}\) (b) \(\mathrm{I}_{2} / \mathrm{NaOH}\) (c) KCN (d) \(\mathrm{CF}_{3} \mathrm{CO}_{3} \mathrm{H}\)

Identify the true statements about methanoic acid. (a) It is formed by heating glycerol with oxalic acid to about \(373 \mathrm{~K}\). (b) It gives formyl chloride when treated with \(\mathrm{PCl}_{5^{*}}\) (c) It is a stronger acid than benzoic acid. (d) It gives carbon monoxide on heating with con. \(\mathrm{H}_{2} \mathrm{SO}_{4}\).
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