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Chapter 5: Problem 32

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

Short Answer

Expert verified
Answer: The correct IUPAC name is 4-chloro-3-oxocyclohex-1-ene.

Step by step solution

01

Understand the SMILES notation and convert it to a molecular structure

The given SMILES notation is: O=C1C=CCCC1Cl Let's break it down: - O=C1: There's a carbonyl group (C=O), and 1 represents the start of a ring structure. - C=CCCC1: This indicates a six-membered ring, with two double bonds. - Cl: A chlorine atom is attached to the ring. Now, let's draw the structure of the compound: ``` Cl | C=C-C=O | | C=C-C-C \___/ ```
02

Determine the correct numbering for the ring

According to IUPAC rules, we'll number the ring in a way that assigns the lowest numbers to the functional groups and double bonds: 1. The carbonyl group C=O will be given the number 1. 2. Next, double bonds will be given lower numbering. 3. Finally, the chlorine atom will be numbered. The numbering of the ring is: ``` Cl | 3=4-1=O | | 2=5-6-C \_/// ```
03

Identify the correct IUPAC name from the given options

With the numbering of the ring: (a) 2 -chlorocyclohex-5-en-1-one → Incorrect. Chlorine is at position 4, not 2, and the double bond is at position 3, not 5. (b) 6 -chlorocyclohex-2-en-1-one → Incorrect. Chlorine is at position 4, not 6, and the double bond is at position 3, not 2. (c) 4 -chloro-3-oxocyclohex-l-ene → Correct. Chlorine is at position 4, carbonyl group (oxo) is at position 1, and the double bond is at position 3. (d) 1 -chloro-2-oxocyclohex-3-ene → Incorrect. The chlorine atom is at position 4, not 1. So, the correct IUPAC name is (c) 4 -chloro-3-oxocyclohex-l-ene.

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Most popular questions from this chapter

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Which of the following pairs will give effervescence with aqueous sodium hydrogen carbonate solution? (a) \(\mathrm{CH}_{3} \mathrm{COCl}\) and \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CO}\) (b) \(\mathrm{CH}_{3} \mathrm{CONH}_{2}\) and \(\left(\mathrm{CH}_{3} \mathrm{CO}\right)_{2} \mathrm{O}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}\) and \(\mathrm{CH}_{3} \mathrm{COOCH}_{3}\) (d) \(\mathrm{CH}_{3} \mathrm{COCl}\) and \(\left(\mathrm{CH}_{3} \mathrm{CO}\right)_{2} \mathrm{O}\)

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