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the heat of hydrogenation of 2,3-pentadiene, a cumulated diene, is 70.5 kcal/mol. what are the relative stabilities of cumulated, conjugated, and isolated dienes?

User Spaceghost
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Final answer:

Conjugated dienes are more stable than both cumulated and isolated dienes due to electron delocalization. The heat of hydrogenation for 2,3-pentadiene is high at 70.5 kcal/mol, indicating lesser stability compared to a conjugated diene. Isolated dienes are generally the least stable due to the lack of delocalization or strain.

Step-by-step explanation:

The heat of hydrogenation for 2,3-pentadiene, which is a cumulated diene, informs us about the relative stabilities of different types of dienes. A cumulated diene has double bonds that share a common carbon atom, while conjugated dienes have alternating single and double bonds, and isolated dienes have two or more single bonds between their double bonds. The heat of hydrogenation is an indirect measure of stability; the lower the heat of hydrogenation, the more stable the compound.

Conjugated dienes are typically more stable than isolated and cumulated dienes because the conjugation allows for delocalization of electrons across the pi system, leading to additional stabilization. The fact that 2,3-pentadiene has a relatively high heat of hydrogenation (70.5 kcal/mol) suggests that it is less stable than a conjugated diene. Isolated dienes are generally considered to be the least stable of the three because they lack the delocalization present in conjugated systems and do not have the strain associated with cumulated dienes. Thus, in terms of stability, we would expect conjugated dienes to be the most stable, followed by cumulated, and finally, isolated dienes being the least stable.

User Natetitterton
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