Question

Consider the Diels-Alder cycloaddition reaction below and complete parts (a)-(b) below.

Consider the Diels-Alder cycloaddition reaction below and complete parts (a)-(b) below. 

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D = deuterium = 2


(a) Draw the major regioisomer (or in other words, constitutional isomer) expected to form. Also, draw appropriate resonance structures to explain why only one constitutional isomer is expected to form. Discuss the interactions between the diene and dienophile that govern this constitutional isomer being the only one expected. 


(b) Redraw the regioisomer from part (a) and show the appropriate stereochemistry using correct dash/wedge notation expected for the major product. Discuss if this is the endo or exo diastereomer and draw a transition-state intermediate to help illustrate why this diastereomer is favored. Also, discuss if you believe this diastereomer is chiral or achiral. If it is chiral, also discuss if you think it will be formed as an equal mixture of two enantiomers (known as racemic).

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