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Stibene (PhCH=CHPh). Can exist in two di...

Stibene `(PhCH=CHPh)`. Can exist in two diastereomeric forms (X) and (Y) and (X) is found to be more soluble in water than (Y). Predict which of the following statement is correct?

A

X is trans isomer

B

Stability of `X gt` Stability of Y

C

Melting point of `X gt` Melting point of Y

D

Boiling point of` 'X gt' Boiling point of Y

Text Solution

AI Generated Solution

The correct Answer is:
To solve the question regarding the diastereomeric forms of stilbene (PhCH=CHPh), we need to analyze the properties of the two forms: cis and trans. Here’s a step-by-step breakdown of the solution: ### Step 1: Identify the Structures - **Cis Stilbene (X)**: In this form, the two phenyl (Ph) groups are on the same side of the double bond. - **Trans Stilbene (Y)**: In this form, the two phenyl groups are on opposite sides of the double bond. ### Step 2: Analyze Polarity - **Cis Stilbene**: The arrangement of the phenyl groups results in a net dipole moment, making this molecule polar. - **Trans Stilbene**: The phenyl groups are positioned opposite each other, which cancels out the dipole moments, making this molecule non-polar. ### Step 3: Solubility in Water - Given that water is a polar solvent, polar molecules tend to be more soluble in water. Since cis stilbene (X) is polar and trans stilbene (Y) is non-polar, it follows that: - **Cis Stilbene (X)** is more soluble in water than **Trans Stilbene (Y)**. ### Step 4: Stability Comparison - **Cis Stilbene (X)** experiences steric hindrance due to the proximity of the bulky phenyl groups, making it less stable. - **Trans Stilbene (Y)** has the phenyl groups positioned far apart, reducing steric hindrance and making it more stable. ### Step 5: Melting and Boiling Points - **Melting Point**: Trans isomers generally have higher melting points due to their symmetrical structure, which allows for better packing in the solid state. Therefore: - **Melting Point of X (cis) < Melting Point of Y (trans)**. - **Boiling Point**: Cis stilbene, being polar, has stronger intermolecular forces compared to the non-polar trans stilbene. Hence: - **Boiling Point of X (cis) > Boiling Point of Y (trans)**. ### Conclusion Based on the analysis: 1. **X is a trans isomer** - Incorrect (X is cis). 2. **Stability of X is greater than stability of Y** - Incorrect (X is less stable). 3. **Melting point of X is greater than melting point of Y** - Incorrect (X has a lower melting point). 4. **Boiling point of X is greater than boiling point of Y** - Correct (X has a higher boiling point). ### Final Answer The correct statement is: **Boiling point of X is greater than boiling point of Y**. ---
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