Chapter 12
Advanced Organic Chemistry. Part A. Structure and Mechanisms · 3 exercises
Problem 1
The bridged radical 1-A has been suggested as a possible intermediate in the photochemical decarbonylation of 3-phenylpropanal. Suggest an experiment to test this hypothesis.
4 step solution
Problem 10
cis-2-Propyl-4- \(t\)-butylcyclohexanone undergoes cleavage to \(4-t\)-butylcyclohexanone on photolysis. The trans isomer does not undergo fragmentation directly, but is converted to the cis isomer, which then fragments. The trans \(\rightarrow\) cis isomerization is quenched by 1,3-pentadiene, but the photofragmentation is not. Offer an explanation of this pronounced stereochemical effect.
4 step solution
Problem 14
In the rearrangement of 4,4 -diphenylcyclocyclohex-2-enone to 5,6 diphenylbicyclo[3.1.0]hexan-2-one, there is a strong preference for formation of the endo phenyl stereoisomer. Offer an explanation for this stereoselectivity.
5 step solution