Solution Found!
The following sequence, beginning with a cyclic hemiacetal
Chapter 22, Problem 22.115(choose chapter or problem)
The following sequence, beginning with a cyclic hemiacetal (compound A), was part of a recently reported enantiospecific synthesis of a powerful sex pheromone (currently used in pest management) of the mealybug Pseudococcus viburni (Tetrahedron Lett. 2010, 51, 5291–5293):
(a) Draw the structures of compounds B and C.
(b) Describe in words how the cyclopentyl ring is closed during the conversion of compound C into compound D.
(c) Identify the reagents you would use to convert compound D into compound F (in just two steps). Also identify the structure of compound E.
Questions & Answers
QUESTION:
The following sequence, beginning with a cyclic hemiacetal (compound A), was part of a recently reported enantiospecific synthesis of a powerful sex pheromone (currently used in pest management) of the mealybug Pseudococcus viburni (Tetrahedron Lett. 2010, 51, 5291–5293):
(a) Draw the structures of compounds B and C.
(b) Describe in words how the cyclopentyl ring is closed during the conversion of compound C into compound D.
(c) Identify the reagents you would use to convert compound D into compound F (in just two steps). Also identify the structure of compound E.
ANSWER:Step 1 of 4
(a) The given cyclic hemiacetal A exists in equilibrium with its open-chain form as given below:
