Indicate the correct set of reactions from the choices below that would accomplish the following synthesis MOST efficiently (Hint: what is the MAJOR product of each step). Br (+ enantiomer) Product Starting Material 1. MeLi then H20, 2. TSCI, pyridine 3. NaBr (excess), heat 1. MeMgBr then HCI, 2. H2SO4, heat, 3. NBS, peroxide, heat 1. LIAIH4 then H2O, 2. H2SO4, heat, 3. HBr O 1. MeMgBr then HCI, 2. H2SO4, heat, 2. HBr, peroxide, light О 1. Н2SO4, MеОН, 2. РОСІ3, pyridine, 3. HBr, CH300CH3, heat m..

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter19: Eas: Electrophilic Aromatic Substitution
Section: Chapter Questions
Problem 45E
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Indicate the correct set of reactions from the choices below that would accomplish
the following synthesis MOST efficiently (Hint: what is the MAJOR product of each
step).
Br
(+ enantiomer)
Product
Starting Material
1. Meli then H20, 2. TSCI, pyridine 3. NaBr (excess), heat
O 1. MeMgBr then HCI, 2. H2SO4, heat, 3. NBS, peroxide, heat
O 1. LIAIH4 then H20, 2. H2S04, heat, 3. HBr
1. MeMgBr then HCI, 2. H2SO4, heat, 2. HBr, peroxide, light
О 1. Н2SO4, MeОН, 2. РОCІ3, pyridine, 3. HBr, CH300CH3, heat
Transcribed Image Text:Indicate the correct set of reactions from the choices below that would accomplish the following synthesis MOST efficiently (Hint: what is the MAJOR product of each step). Br (+ enantiomer) Product Starting Material 1. Meli then H20, 2. TSCI, pyridine 3. NaBr (excess), heat O 1. MeMgBr then HCI, 2. H2SO4, heat, 3. NBS, peroxide, heat O 1. LIAIH4 then H20, 2. H2S04, heat, 3. HBr 1. MeMgBr then HCI, 2. H2SO4, heat, 2. HBr, peroxide, light О 1. Н2SO4, MeОН, 2. РОCІ3, pyridine, 3. HBr, CH300CH3, heat
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