2 steps BU4NF C9H1602 A + B ÓSIME,tBu (i) Enone C can be prepared from alkyne A and aldehyde B in two steps via a gold-catalysed reaction. Identify A and B and provide reagents/conditions for a synthesis of C. (ii) Give the structure of D and classify the ring-closing reaction for its formation from C according to Baldwin's rules

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution
Section16.SE: Something Extra
Problem 45MP
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Answer ALL parts.
(a)
Treatment of enone C with tetrabutylammonium fluoride leads to the formation of
heterocycle D.
2 steps
BU4NF
C9H1602
A + B
D
OSIME,tBu
(i)
Enone C can be prepared from alkyne A and aldehyde B in two steps via a
gold-catalysed reaction. Identify A and B and provide reagents/conditions
for a synthesis of C.
(ii)
Give the structure of D and classify the ring-closing reaction for its
formation from C according to Baldwin's rules
(iii)
Sketch the key molecular orbitals involved in the ring-closing reaction in
part (ii) and hence explain whether the reaction is favourable or
unfavourable.
Transcribed Image Text:Answer ALL parts. (a) Treatment of enone C with tetrabutylammonium fluoride leads to the formation of heterocycle D. 2 steps BU4NF C9H1602 A + B D OSIME,tBu (i) Enone C can be prepared from alkyne A and aldehyde B in two steps via a gold-catalysed reaction. Identify A and B and provide reagents/conditions for a synthesis of C. (ii) Give the structure of D and classify the ring-closing reaction for its formation from C according to Baldwin's rules (iii) Sketch the key molecular orbitals involved in the ring-closing reaction in part (ii) and hence explain whether the reaction is favourable or unfavourable.
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