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The following sequence of reactions was used to synthesize compound D. In all steps, the product of the preceding step is used in the
The following sequence of reactions was used to synthesize compound D. In all steps, the product of the preceding step is used in the subsequent step. R R= non-protic strong electron donating ether group FeBr/Br Compound A Condition 1 Compound A Grignard Reagent 1. (R)-3-methylpentanal in THF 2. acid workup TsCI, pyridine Compound C Compound B Ts = Tosyl group strong bulky base Compound D Degree of Unsaturation = 5 i)For each of the reactions in the above synthetic scheme, draw the major product (compounds A-D) of the reaction. Show all possible stereoisomers of compounds B and assign R/S nomenclature where relevant. Correctly identify the relationship(s) between the pair(s) of stereoisomer(s). ii) Write down the reaction conditions for 1 highlighting the actions to be taken for efficient formation of Grignard reagent. iii) Draw the accepted mechanism for the conversion of Compound C to D. Comment on the stereochemistry of the product. iv) Suggest the peaks expected in the region from 5-9 ppm on the 1H NMR spectrum for compound D, showing approx. chemical shift region, multiplicity, number of hydrogens and the corresponding partial structure.
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