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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

Which of the following halides will not give good yield of the corresponding acid by the conversion to cyanide, followed by hydrolysis? (a) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{Br}\) (b) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CBr}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}\) (d) CC1CCCCC1

A compound (A) (which gives haloform reaction), on reduction with zinc amalgam and conc.HCl gives (B). (B) is also obtained by treating \(1,1,2,2\) - tetrachlorobutane with zinc dust. The compound (A) is (a) C#CC(C)O (b) C=C(C)C=O (c) C=CC(C)O (d) C#CC=O

The IUPAC name of is CCC(C=O)CC(C)C (a) 2 -ethyl-4-methylpentanal (b) 4 -methyl 2 -ethylpentanal (c) 2 -methylhexanal (d) 2 -ethylhexanal

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

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 Eventhough carboxylic acids contain a \(>C=O\) group, they do not give the characteristic reaction of carbonyl compounds. and Statement 2 The electrophilicity of carbonyl carbon is less in carboxylic acids due to resonance.
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