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Which Series of Reactions Described Below Will Result in the Formation

Question 48

Multiple Choice

Which series of reactions described below will result in the formation of compound A, starting with compound B? Which series of reactions described below will result in the formation of compound A, starting with compound B? A) 1. HO-(CH<sub>2</sub>) <sub>2</sub>-OH /trace H<sub>3</sub>O<sup>+</sup> 2) DMSO (COCl<sub>2</sub>) /Et<sub>3</sub>N, CH<sub>2</sub>Cl<sub>2</sub> 3) MgBr-(CH<sub>2</sub>) <sub>2</sub>-CH<sub>3</sub>/diethyl ether 4) work-up with H<sub>3</sub>O<sup>+</sup> <sup>5. PCC</sup> B) 1. PCC 2) SOCl<sub>2</sub> 3) LiCu-((CH<sub>2</sub>) <sub>2</sub>-CH<sub>3</sub>) <sub>2</sub> 4) work-up with H<sub>3</sub>O<sup>+</sup> C) 1. Na<sub>2</sub>Cr<sub>2</sub>O<sub>7</sub>/H<sub>2</sub>SO<sub>4</sub> 2) SOCl<sub>2</sub> 3) 2 MgBr-(CH<sub>2</sub>) <sub>2</sub>-CH<sub>3</sub>/diethyl ether 4) work-up with H<sub>3</sub>O<sup>+</sup> D) both A and B E) both B and C


A) 1. HO-(CH2) 2-OH /trace H3O+
2) DMSO (COCl2) /Et3N, CH2Cl2
3) MgBr-(CH2) 2-CH3/diethyl ether
4) work-up with H3O+
5. PCC
B) 1. PCC
2) SOCl2
3) LiCu-((CH2) 2-CH3) 2
4) work-up with H3O+
C) 1. Na2Cr2O7/H2SO4
2) SOCl2
3) 2 MgBr-(CH2) 2-CH3/diethyl ether
4) work-up with H3O+
D) both A and B
E) both B and C

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