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Chapter 3: Problem 40

The products formed when toluene is treated with ozone and the product is subjected to reduction with zinc dust and water are (a) Glyoxal and acetaldehyde (b) Glyoxal and acetone (c) Formaldehyde and acetaldehyde (d) Glyoxal and methyl glyoxal

Short Answer

Expert verified
Answer: Formaldehyde and glyoxal.

Step by step solution

01

Write the structure of Toluene

Toluene is a derivative of Benzene with a methyl group attached to it. Write the structure of toluene as: C6H5-CH3
02

Identify the Cleavage Sites (Double Bond)

For ozonolysis, we have to identify the double bonds in the molecule that will be cleaved. Toluene has no double bonds within its linear carbon structure, but the benzene ring is composed of alternating single and double carbon-carbon bonds.
03

Perform Ozonolysis on Toluene

In this case, with ozonolysis occurring on the double bonds in the benzene ring, a molecule of ozone (O3) attacks the double bonds, forming the unstable ozonide intermediate. Then, the ozonide is reduced with zinc dust and water to produce glyoxal (CHO-CHO) and a 1-carbon species.
04

Identify Products

Based on the ozonolysis result, the products formed are glyoxal (CHO-CHO) and the 1-carbon species. Upon inspection of the options given, we must now determine if this 1-carbon species is an aldehyde or a ketone. Since toluene has the methyl group attached (CH3), the 1-carbon product will have an aldehyde functional group rather than a ketone. This yields the product formaldehyde (HCHO).
05

Choose the Correct Option

Based on our analysis, the correct products formed are glyoxal (CHO-CHO) and formaldehyde (HCHO). Therefore, the correct answer is: (c) Formaldehyde and acetaldehyde

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Most popular questions from this chapter

The wrong statement relating to the influence of substituents on aromatic electrophilic substitution reactions is (a) The rate determining step in an electrophilic substitution is the one which leads to the formation of an arenium ion. (b) Electron releasing groups make the transition state more stable and the transition state resembles the arenium ion. (c) The arenium ion is a highly energetic intermediate and the step that leads to it is a highly exothermic step. (d) An electron withdrawing substituent makes the arenium ion less stable and the transition state leading to such an arenium ion is less stable.

Statement 1 \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{N}\left(\mathrm{CH}_{3}\right)_{3}\) gives meta nitro derivative on nitration almost exclusively. and Statement 2 All deactivating groups are meta directing groups.

The increasing order of acidic strength among p-methoxyphenol, p-cresol and p-nitrophenol is (a) p-cresol \(<\) p-methoxyphenol \(<\) p-nitrophenol (b) p-methoxyphenol \(<\) p-cresol \(<\) p-nitrophenol (c) \(\mathrm{p}\) -cresol \(<\mathrm{p}\) -nitrophenol \(<\mathrm{p}\) -methoxyphenol (d) p-methoxyphenol \(<\) p-nitrophenol \(<\mathrm{p}\) -cresol

Which of the following structures is not aromatic?

o-Nitrophenol has lower \(\mathrm{pK}\) than (a) p-nitrophenol (b) o-cresol (c) o-fluorophenol (d) \(\mathrm{p}\) -methoxyphenol
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