Problem 32 O=C1C=CCCC1Cl The IUPAC name of ... [FREE SOLUTION]

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IIT JEE Super Course in Chemistry: Organic Chemistry

Trishna Knowledge Systems

Chemistry

2012 Edition

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

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 \___/ ```

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 \_/// ```

Identify the correct IUPAC name from the given options

With the numbering of the ring: (a) 2 -chlorocyclohex-5-en-1-one 鈫� 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 鈫� 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 鈫� 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 鈫� 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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91影视

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

Step by step solution

Understand the SMILES notation and convert it to a molecular structure

Determine the correct numbering for the ring

Identify the correct IUPAC name from the given options

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