Question

Please show detailed arrow-pushing mechanism.

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C) Please provide the product of the following reaction and concisely explain why you get the observed constitutional isomer. Drawing the appropriate orbitals will really help to explain your answer. (2 points box, 4 points explanation, 6 points total section). 1 H O-Na H Mel

Answer 1

1. The given reaction is an example for the Base catalysed promotion of Nucleophilic Substitution reaction. Here the Base is sodium t-butoxide which abstract the ACIDIC proton of the bicyclic ketone which is present in the ALPHA position,

2. Since, there presence of the two types of the ALPHA protons, one is present in the BRIDGED HEAD CARBON ATOM which is the inert proton, because of the RIGIDITY of the bridged head carbon atom, So it does not undergoes to the reaction with BASE.

3. So the another type of the proton (ALPHA-HYDROGEN) undergoes for the reaction with the base, and thereby the formation of the Carbanion.  Which attacks the Methyl iodide, (NUCLEOPHILIC SUBSTITUTION REACTION). And yields the product. Which is given as follows,
но

And its mechanism for the following reaction is given as

A Bicyclic ketone, with x- hydrogens indicated as las and (b)". A ) is the x-hydrogen las is placed in the bridged head carbon of the bicyclo compound. in the ar hydrogens (b) is a methylene (-ele) group" (ny since k- hydrogen ca on briged head carbon atom is highly ig inort for the reactions, because of the "rigid briged head carbon atom". H "Hydrogen "Rigid carbon aton" also rigid and inext for the reaction". Because of the formation of highly strained ring. - "Unstable"

+ "Sodium terstany butoaide the It acts as as a a strong base strong bat and abstracts to the carbonyl group. x- hydrogen atom Mechanism :- enolate This cannot be abstraited by the base, due to formation of highly strained enolate Resonance structures substitution with me I: me. I i product