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Basics of Organic Chemistry question

2016 · 9 Apr · Shift 1 · Q8
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Basics of Organic Chemistry question

2016 · 9 Apr · Shift 1 · Q8

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
The hydrocarbon with seven carbon atoms containing a neopentyl and a vinyl group is :
  1. A
    2, 2-dimethyl-4-pentene
  2. B
    Isopropyl-2-butene
  3. C
    4, 4-dimethylpentene
  4. D
    2, 2-dimethyl-3-pentene
View written solutionFree

Correct answer: C

  1. Identify the required groups

    We need a hydrocarbon with 7 carbon atoms that contains:

    • a neopentyl group: \ce(CH3)3C−CH2−\ce{(CH3)3C-CH2-}\ce(CH3)3C−CH2−
    • a vinyl group: \ceCH2=CH−\ce{CH2=CH-}\ceCH2=CH−
  2. Combine the two groups

    If a molecule contains both neopentyl and vinyl groups, its structure can be written as: \ceCH2=CH−CH2−C(CH3)3\ce{CH2=CH-CH2-C(CH3)3}\ceCH2=CH−CH2−C(CH3)3

    Count carbons:

    • vinyl part: 222 carbons
    • \ceCH2\ce{CH2}\ceCH2 linker: 111 carbon
    • quaternary carbon: 111 carbon
    • three methyl groups: 333 carbons

    Total =2+1+1+3=7= 2+1+1+3 = 7=2+1+1+3=7 carbons.

  3. Find the IUPAC name of this structure

    Structure: \ceCH2=CH−CH2−C(CH3)3\ce{CH2=CH-CH2-C(CH3)3}\ceCH2=CH−CH2−C(CH3)3

    Choose the longest chain containing the double bond: \ceCH2=CH−CH2−C−CH3\ce{CH2=CH-CH2-C-CH3}\ceCH2=CH−CH2−C−CH3

    This gives a pentene chain. Number from the double-bond end to give the alkene lowest locant:

    • double bond at carbon 111
    • two methyl substituents at carbon 444

    Therefore, the name is: 4,4-dimethyl-1-pentene\boxed{4,4\text{-dimethyl-1-pentene}}4,4-dimethyl-1-pentene​

  4. Match with the options

    Among the given options, option C: 4, 4-dimethylpentene represents this structure (the position of double bond is omitted in the option, but it corresponds to the required neopentyl + vinyl arrangement).

  5. Check other options briefly

    • A: 2,2-dimethyl-4-pentene corresponds to a different skeleton; it does not contain the neopentyl fragment.
    • B: Isopropyl-2-butene has only 666 carbons, not 777.
    • D: 2,2-dimethyl-3-pentene also does not give the neopentyl + vinyl combination.
  6. Final answer

    The required hydrocarbon is: C\boxed{\text{C}}C​

  7. Comparison with stored answer

    Stored correct answer: C

    My derived answer also is C, so they agree.

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