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Q9.9:
Draw the cis and trans structures of hex-2-ene. Which isomer will have higher b.p. and why?

Solution :

Step 1: Structural Representation of Hex-2-ene

Hex-2-ene has the molecular formula $C_6H_{12}$. The double bond is positioned between the second and third carbon atoms. The structure is $CH_3-CH=CH-CH_2-CH_2-CH_3$. Geometrical isomerism arises due to restricted rotation about the $C=C$ double bond.

Step 2: Drawing Cis and Trans Isomers

In the cis isomer, the high-priority groups (the methyl group and the propyl group) are on the same side of the double bond. In the trans isomer, they are on opposite sides.

C=C CH₃ H CH₂CH₂CH₃ H Cis-hex-2-ene C=C CH₃ H CH₂CH₂CH₃ H Trans-hex-2-ene

Step 3: Boiling Point Analysis

The boiling point of an isomer is influenced by its molecular polarity (dipole moment) and molecular packing. [Per the principles of Intermolecular Forces]:

  • Cis-isomer: The alkyl groups are on the same side, resulting in a net dipole moment ($\mu \neq 0$). This creates a polar molecule with stronger dipole-dipole interactions between molecules.
  • Trans-isomer: The alkyl groups are on opposite sides, causing the bond dipoles to cancel each other out, resulting in a non-polar or weakly polar molecule ($\mu \approx 0$).

Step 4: Comparative Summary

Property Cis-hex-2-ene Trans-hex-2-ene
Dipole Moment Higher Lower/Zero
Intermolecular Force Stronger (Dipole-Dipole) Weaker (London Dispersion)

Because the cis isomer possesses a greater net dipole moment, it experiences stronger intermolecular dipole-dipole attractions than the trans isomer. Consequently, more thermal energy is required to overcome these forces to transition the substance from the liquid phase to the gas phase.

Final Solution: The cis-hex-2-ene isomer has a higher boiling point because its structure leads to a net molecular dipole moment, resulting in stronger dipole-dipole intermolecular attractions compared to the non-polar or less polar trans-hex-2-ene isomer.


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