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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

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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 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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