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Chapter 5: Problem 96

O=Cc1ccc([N+](=O)[O-])cc1 $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOK}$ CC(=O)Cc1ccc(N)cc1 The reagent (X) in the above reaction is (a) \(\mathrm{BrCH}_{2} \mathrm{CH}_{2} \mathrm{COOH}\) (b) \(\left(\mathrm{CH}_{3} \mathrm{CO}\right)_{2} \mathrm{O}\) (c) \(\left(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CO}\right)_{2} \mathrm{O}\) (d) \(\left(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COO}\right)_{2}\)

Short Answer

Expert verified
Answer: (c) \(\left(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CO}\right)_{2} \mathrm{O}\).

Step by step solution

01

Convert the SMILES to structural formulas

Start by converting the given SMILES format to structural formulas to see the reactions taking place: Starting material: O=Cc1ccc([N+](=O)[O-])cc1 Reaction after adding \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOK}\) Product: CC(=O)Cc1ccc(N)cc1
02

Identify the reaction type

Upon analyzing the structural formulas, we can see that this appears to be a reduction reaction with an organic ketone, giving the following reaction: Ketone: O=Cc1ccc([N+](=O)[O-])cc1 Reductant: \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOK}\) Product: CC(=O)Cc1ccc(N)cc1
03

Determine the possible reagents (X)

With the reaction type identified, we can now focus on the possible reagents (X): (a) \(\mathrm{BrCH}_{2} \mathrm{CH}_{2} \mathrm{COOH}\) (b) \(\left(\mathrm{CH}_{3} \mathrm{CO}\right)_{2} \mathrm{O}\) (c) \(\left(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CO}\right)_{2} \mathrm{O}\) (d) \(\left(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COO}\right)_{2}\)
04

Analyze the options and determine the correct reagent (X)

Option (a) involves a bromoalkanoic acid, which would not suffice as a reducing agent for an organic ketone. Option (b) involves acetic anhydride, which is a reagent used in acylation reactions. Option (c) involves ethyl acetate anhydride, which can be used to reduce organic ketones along with a strong base such as \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOK}\). Option (d) involves diethyl oxalate, which is not suitable for reducing organic ketones. Based on these analyzes, the most suitable reagent (X) is option (c): \(\left(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CO}\right)_{2} \mathrm{O}\).

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Most popular questions from this chapter

The trimer of acetaldehyde is known as (a) formalin (b) trioxane (c) paraldehyde (d) metaldehyde

The compound that forms a stable hemiacetal when treated with \(\mathrm{CH}_{3} \mathrm{OH}\) and dry \(\mathrm{HCl}\) is (a) benzaldehyde (b) cyclohexanone (c) cyclopropanone (d) propanone

When acetic acid is treated with aqueous sodium bicarbonate, \(\mathrm{CO}_{2}\) gas is evolved. The 'Carbon' of \(\mathrm{CO}_{2}\) comes from (a) carboxyl group (b) methyl group (c) bicarbonate (d) both carboxyl group and bicarbonate

O=C1C=CCCC1Cl The IUPAC name of (a) 2 -chlorocyclohex-5-en-1-one (b) 6 -chlorocyclohex-2-en-1-one (c) 4 -chloro-3-oxocyclohex-l-ene (d) 1 -chloro-2-oxocyclohex-3-ene

When distilled with concentrated sulphuric acid, propanone gives (a) monomethyl benzene (b) dimethyl benzene (c) trimethyl benzene (d) propanoic acid
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