Chapter 28: 44 P (page 1212)
A student found that heating any one of the isomers shown here resulted in scrambling of the deuterium to all three positions on the five-membered ring. Propose a mechanism to account for this observation.
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Explain why two different products are formed from disrotatory ring closure of (2E,4Z,6Z)-octatriene, but only one product is formed from disrotatory ring closure of (2E,4Z,6E)-octatriene.
Will a concerted reaction take place between 1,3-butadiene and 2-cyclohexenone in the presence of ultraviolet light?
Problem:Which of the following are correct? Correct any false statements.
a. A conjugated diene with an even number of double bonds undergoes conrotatory ring closure under thermal conditions.
b. A conjugated diene with an antisymmetric HOMO undergoes conrotatory ring closure under thermal conditions.
c. A conjugated diene with an odd number of double bonds has a symmetric HOMO.
a. Identify the mode of ring closure for each of the following electrocyclic reactions.
b. Are the indicated hydrogens cis or trans?
Show how the reactant can be converted to the product in two steps.
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