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Q9.3(a):
For the following compounds, write structural formulas and IUPAC names for all possible isomers having the number of double or triple bond as indicated : (a) $C_4H_8$ (one double bond)

Solution :

Step 1: Determining the Degree of Unsaturation (Double Bond Equivalent)

To identify the number of rings or pi bonds in the molecular formula $C_4H_8$, we apply the Degree of Unsaturation (DoU) formula:

$DoU = C + 1 - \frac{H}{2} + \frac{N}{2} - \frac{X}{2}$

$DoU = 4 + 1 - \frac{8}{2} = 5 - 4 = 1$

[Per the Degree of Unsaturation principle, a value of 1 indicates either one double bond or one ring structure.]

Since the problem specifies one double bond, we must construct all possible acyclic isomers containing four carbons and one $C=C$ unit.

Step 2: Systematic Structural Isomerism Generation

We generate the isomers based on the position of the double bond and the branching of the carbon chain.

Isomer Structural Formula IUPAC Name
1 $CH_2=CH-CH_2-CH_3$ But-1-ene
2 $CH_3-CH=CH-CH_3$ But-2-ene
3 $CH_2=C(CH_3)-CH_3$ 2-Methylprop-1-ene

Step 3: Geometrical Considerations (Stereoisomerism)

Within the isomers identified, But-2-ene exhibits geometric isomerism due to restricted rotation around the $C=C$ bond. [Per the Cahn-Ingold-Prelog priority rules and geometric constraints].

CH₃ CH₃ H H cis-but-2-ene CH₃ CH₃ H H trans-but-2-ene

Step 4: Comprehensive List of Isomers

  • But-1-ene: Straight chain, double bond at position 1.
  • cis-But-2-ene: Straight chain, double bond at position 2, methyl groups on the same side.
  • trans-But-2-ene: Straight chain, double bond at position 2, methyl groups on opposite sides.
  • 2-Methylprop-1-ene: Branched chain (isobutylene), double bond at position 1.

Final Solution: The possible structural isomers for $C_4H_8$ are But-1-ene, But-2-ene (as cis/trans stereoisomers), and 2-Methylprop-1-ene.


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