JEE Main · 2019 · Shift-IImediumHALO-005

What is the IUPAC name of the following compound?

Haloalkanes & Haloarenes · Class 12 · JEE Main Previous Year Question

Question

What is the IUPAC name of the following compound? image

Options
  1. a

    3-Bromo-1,2-dimethylbut-1-ene

  2. b

    3-Bromo-3-methyl-1,2-dimethylprop-1-ene

  3. c

    2-Bromo-3-methylpent-3-ene

  4. d

    4-Bromo-3-methylpent-2-ene

Correct Answerd

4-Bromo-3-methylpent-2-ene

Detailed Solution

Step 1: Identify the structure from the image

Structure: \ceCH3C(CH3)=C(H)CH(Br)CH3\ce{CH3-C(CH3)=C(H)-CH(Br)-CH3}

Step 2: Find the longest carbon chain

Longest chain: 5 carbons → pentane

Step 3: Number the chain

Rule: Give the double bond the lowest number.

  • Numbering from left: Double bond at C-2
  • Numbering from right: Double bond at C-3

Choose left to right: C-2 has the double bond (lower number)

C1: CH3
C2: C (with CH3 substituent)
C3: C (double bond to C2)
C4: CH (with Br substituent)  
C5: CH3

Step 4: Identify substituents

  • Bromine at C-4: 4-bromo
  • Methyl at C-3: 3-methyl
  • Double bond between C-2 and C-3: pent-2-ene

Step 5: Write IUPAC name

Alphabetical order: bromo before methyl

4-Bromo-3-methylpent-2-ene

Answer: (d)

Key IUPAC Rules:

  1. Longest carbon chain with functional group
  2. Number to give functional group (double bond) lowest number
  3. Name substituents alphabetically
  4. Use hyphens between numbers and words, commas between numbers

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