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Q9.3(b):
For the following compounds, write structural formulas and IUPAC names for all possible isomers having the number of double or triple bond as indicated : (b) $C_5H_8$ (one triple bond)

Solution :

Given Molecular Formula and Constraint

Formula: $C_5H_8$
Constraint: One triple bond (Alkyne degree of unsaturation: $2$)

The general formula for an alkyne is $C_nH_{2n-2}$. For $n=5$, $C_5H_{2(5)-2} = C_5H_8$. This confirms the presence of one triple bond [Per the Degree of Unsaturation formula: $DU = C + 1 - \frac{H}{2} = 5 + 1 - 4 = 2$].

Step 1: Identifying Linear Isomers (Straight Chain)

We rearrange the carbon backbone to place the triple bond at different terminal or internal positions.

  • Isomer 1: Pent-1-yne
    Structure: $CH \equiv C - CH_2 - CH_2 - CH_3$
    IUPAC Name: Pent-1-yne
  • Isomer 2: Pent-2-yne
    Structure: $CH_3 - C \equiv C - CH_2 - CH_3$
    IUPAC Name: Pent-2-yne

Step 2: Identifying Branched Isomers

We reduce the parent chain length to 4 carbons and place a methyl substituent.

  • Isomer 3: 3-Methylbut-1-yne
    Structure: $CH \equiv C - CH(CH_3) - CH_3$
    IUPAC Name: 3-Methylbut-1-yne

Step 3: Visual Representation of Structural Isomers

Pent-1-yne CH≡C-CH₂-CH₂-CH₃ Pent-2-yne CH₃-C≡C-CH₂-CH₃ 3-Methylbut-1-yne CH≡C-CH(CH₃)₂

Summary of Isomeric Analysis

Structural Formula IUPAC Name
$CH \equiv C - CH_2 - CH_2 - CH_3$ Pent-1-yne
$CH_3 - C \equiv C - CH_2 - CH_3$ Pent-2-yne
$CH \equiv C - CH(CH_3) - CH_3$ 3-Methylbut-1-yne

Final Solution: The three possible structural isomers for $C_5H_8$ containing one triple bond are Pent-1-yne, Pent-2-yne, and 3-Methylbut-1-yne.


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