Chapter 27: Q 1. (page 1078)
Question: Classify each reaction as an electrocyclic reaction, a cycloaddition, or a sigmatropic rearrangement. Label the σ bonds that are broken or formed in each reaction.
Short Answer
Answer
Chapter 27: Q 1. (page 1078)
Question: Classify each reaction as an electrocyclic reaction, a cycloaddition, or a sigmatropic rearrangement. Label the σ bonds that are broken or formed in each reaction.
Answer
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Get started for freeQuestion:Using orbital symmetry, explain why a Diels–Alder reaction does not take place under photochemical reaction conditions.
Question: (a) What product is formed when each compound undergoes a thermal electrocyclic ring opening? (b) What product is formed when each compound undergoes a photochemical electrocyclic ring opening?
Question: The endiandric acids comprise a group of unsaturated carboxylic acids isolated from a tree that grows in the rain forests of eastern Australia. The methyl esters of endiandric acids D and E have been prepared from polyene Y by a series of two successive electrocyclic reactions: thermal ring closure of the conjugated tetraene followed by ring closure of the resulting conjugated triene. (a) Draw the structures (including stereochemistry) of the methyl esters of endiandric acids D and E. (b) The methyl ester of endiandric acid E undergoes an intramolecular [4 + 2] cycloaddition to form the methyl ester of endiandric acid A. Propose a possible structure for endiandric acid A.
Question: [4 + 2] Cycloadditions with o-quinones such as B are often complex because a variety of products are possible.a. Draw arrows to illustrate how each product is formed when B reacts with styrene, and label the “diene” and “dienophile” components.
b. Draw arrows to illustrate how each product is formed when B reacts with buta-1,3-diene, and label the “diene” and “dienophile” components.
c. o-Quinone C reacts with diene D to form heterocycle E by a process that involves a cycloaddition followed by a [3,3] sigmatropic rearrangement. Use curved arrows to illustrate how this two-step sequence occurs. E is not formed directly from C by a Diels– Alder reaction.
Question: Explain why heating buta-1,3-diene forms 4-vinylcyclohexene but not cycloocta-1,5-diene.
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