trans-Cyclooctene has a chiral plane and a high barrier for racemization. The double bond of trans-c — Analytical Chemistry Chemistry Question
Twist & Chirality
trans-Cyclooctene has a chiral plane and a high barrier for racemization. The double bond of trans-cyclooctene is twisted, as a result, the molecule displays unusual reactivity in cycloaddition reactions.
In 2011, Fox and coworkers developed a photochemical synthesis towards a variety of trans- cyclooctene derivatives. The process is non-stereocontrolled and the synthetic scheme is as follow.
Draw all possible stereoisomers of compound 3 that could be obtained from the reduction of compound 2. Not necessary to assign R,S configuration.
i) If one of the stereoisomers of compound 3 is converted to compound 4, how many stereoisomeric form(s) of compound 4 will be obtained?
ii) The number of possible stereoisomeric form(s) of compound 4 =
iii) If there are more than one stereoisomer, is it possible to separate the obtained stereoisomers of compound 4 by achiral chromatography? Tick the relevant circle.
Yes No
Model Answer
There can exist 2 stereoisomeric forms of compound 4.
The correct answer is: No