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HW #20 Key - organic product is formed in the reaction draw...

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Bocknack CH 310M/318M Fall 2008 Graded Homework Problem #20 – Answer Key Deadline : 3:00 p.m., Thursday, 12/4/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. In each part below, predict the structure(s) of the major organic product(s) that will form when the given starting material is subjected to the indicated reaction conditions. If two different products are formed, draw both of them, one structure in each box. Be sure to show any stereochemistry clearly and unambiguously where necessary. Remember, stereoisomers are different compounds, so if more than one stereoisomer forms as a result of the reaction, you should draw BOTH of them! If only one
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Unformatted text preview: organic product is formed in the reaction, draw it in one of the boxes, and fill the other box with the symbol “X”. If no reaction occurs under the indicated conditions, fill both boxes with the symbol “X”. (a) + (b) + (c) + (d) + (e) + Br H 3 C H CH 3 Br CH 3 SNa DMF (solvent) Br KOC(CH 3 ) 3 , Δ (CH 3 ) 3 COH (solvent) Br H NaOCH 2 CH 3 , Δ CH 3 CH 2 OH (solvent) O H CN HBr KOH, Δ 20% H 2 O/80% acetone (solvent) O H H 3 C H CH 3 H H 3 C OH CH 3 (racemic, via S N 1) SCH 3 (via S N 2) (via E2) (both diastereomers of the Zaitsev alkene form via E2) Br CN NC Br (racemic, via S N 1)...
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