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Q.73 Chemistry ⭐ 360° Option Elimination Active
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NEET 2021 Chemistry Question 73 Solution

Topic: Hydrocarbons · Official NTA Booklet Code M1
NEET 2021 Chemistry Question 73: IUPAC Structure Verification: 2,6-Dimethyl-dec-4-ene

Question

The correct structure of 2,6-Dimethyl-dec-4-ene is:

✓
Verified Against NTA Final Answer Key
Option (1) : Structure (1)
📚 Hydrocarbons Medium
📋 Given Parameters & Problem Setup
Target Compound 2,6-Dimethyl-dec-4-ene
Main Chain 10 carbon atoms (dec-)
Principal Unsaturation Double bond at C-4 (dec-4-ene)
Substituents Two methyl groups at C-2 and C-6
⚡

The 30-Second Exam Hall Shortcut: ⚡ IUPAC Locant Verification: 2-Methyl + C4=C5 + 6-Methyl

⏱️ Save ~25 seconds

Number from the end that gives lowest locant to the double bond: Top right is isopropyl (C1−C2(CH3)−C_1-C_2(CH_3)-). Then C3(CH2)C_3(CH_2), then double bond starts at C4C_4 (C4=C5C_4=C_5). Carbon C6C_6 carries the second methyl group, followed by a 4-carbon butyl chain (C7−C8−C9−C10C_7-C_8-C_9-C_{10}). Total chain = 10 carbons (dec-4-ene) with methyls at 2 and 6. This is uniquely Structure (1)! Match Option (1)!

1 Target IUPAC: 2,6-Dimethyldec-4-ene.
2 Check main chain length: 10 carbons.
3 Double bond must be at position 4 (between C4 and C5).
4 In Structure (1): - C1: terminal methyl - C2: CH with methyl branch - C3: CH2 - C4=C5: double bond - C6: CH with methyl branch - C7 to C10: butyl chain (-CH2-CH2-CH2-CH3). All locants match perfectly (2,6-dimethyldec-4-ene).
5 In Structure (3), the double bond is between C3 and C4 (dec-3-ene).
6 Match Option (1).
🛡️
Why You Can 100% Trust This Shortcut: Canonical IUPAC rules for naming branched alkenes.
📐

Step-by-Step Rigorous Workflow & Mathematical Proof

Step 1

Decoding the IUPAC Name 2,6-Dimethyl-dec-4-ene

Break down the IUPAC components: - Root word: dec   ⟹  \implies longest continuous carbon chain containing the double bond has 10 carbon atoms. - Suffix: -4-ene   ⟹  \implies double bond is between carbon-4 and carbon-5. - Substituents: 2,6-dimethyl   ⟹  \implies methyl groups (−CH3-CH_3) are located at carbon-2 and carbon-6.

Step 2

Verifying Structure (1)

Trace the carbon skeleton of Structure (1) starting from the right-hand isopropyl terminus: - C1C_1: terminal methyl group - C2C_2: carbon with vertical methyl branch - C3C_3: −CH2−-CH_2- methylene carbon - C4=C5C_4=C_5: internal double bond (dec-4-ene) - C6C_6: carbon with methyl branch - C7−C8−C9−C10C_7-C_8-C_9-C_{10}: linear butyl tail (−CH2−CH2−CH2−CH3-CH_2-CH_2-CH_2-CH_3) Total carbon chain length =10= 10. The double bond is at position 4, and substituents are at 2 and 6. Thus, Structure (1) is identically 2,6-dimethyldec-4-ene.

Step 3

Eliminating Alternative Structures

- Structure (2): Double bond is located towards the bottom at position 5 or 6. - Structure (3): The double bond connects directly to the carbon adjacent to C2, placing the double bond at position 3 (dec-3-ene). - Structure (4): The double bond is located between the branch carbon and the next carbon, giving an incorrect substituent position.

⭐

360° Option Elimination Engine Key Feature

Diagnose every choice: Know exactly why the right option works and why distractors fail.

4-Option Deep Scan
1 1
✓ 100% Correct
Verdict & Scientific Reason:

Flawless structure of 2,6-dimethyldec-4-ene with 10 carbons in parent chain and correct locants.

💡
Why this is airtight: None; rigorous IUPAC skeleton verification.
2 2
✗ Incorrect
Verdict & Scientific Reason:

Double bond is located at position 5/6, not position 4.

⚠️
Student Fallacy (Why candidates pick this trap): Incorrect locant numbering.
3 3
✗ Incorrect
Verdict & Scientific Reason:

Double bond is at position 3 (2,6-dimethyldec-3-ene).

⚠️
Student Fallacy (Why candidates pick this trap): Missing the methylene spacer between C2 and double bond.
4 4
✗ Incorrect
Verdict & Scientific Reason:

Double bond is at position 2, directly at the branch point.

⚠️
Student Fallacy (Why candidates pick this trap): Misplacing double bond at branch carbon.
⚠️

NTA Trap Alert: Counting Vertices in Skeletal Bond-Line Formulas Trap

In bond-line structures, candidates frequently mistake Structure (3) for the answer by miscounting the single bond between the isopropyl group and the double bond. In Structure (3), only 1 carbon separates C2 and the alkene, making it dec-3-ene. In Structure (1), a full methylene (−CH2−-CH_2-) group exists at C3, making it dec-4-ene.

🛡️ How to avoid the -1 mark: Count vertices sequentially from C1: C1→C2(methyl)→C3→C4=C5C_1 \to C_2(\text{methyl}) \to C_3 \to C_4=C_5. Only Structure (1) has the double bond at C4.
📖

Core NEET Syllabus Standard

NCERT Chemistry · Hydrocarbons Standard Benchmark
Core Scientific Principle Tested:

"IUPAC rules dictate selecting the longest chain containing the double bond and numbering from the end that gives the double bond the lowest locant."

Syllabus Focus: Nomenclature of Alkenes
✓ Core NEET UG Syllabus Anchor Syllabus & Academic Standards ↗

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