CHEM 205 Worksheet (WS6) 63 Points Total

Key Topics: Elimination Reactions (E2 & E1), Substitution Reactions (SN2 & SN1) and using reagents that can convert OH into better leaving group (that don’t involve carbocation formation).

1. (24pts) In the empty boxes, draw the bond-line structure of the E2 products indicated. Where applicable, show stereochemistry clearly. (3pts for each correct product indicated)

2. (20 pts) Each arrow below represents a step. In the correct order, write/draw in the missing reagent(s)  or reactants needed above each reaction arrow to complete each two-step syntheses and to obtain the major product shown. Use only reactions introduced thus far in CHEM 205. (2pts each correct step)

3. Consider the reaction shown below.

(a) (9pts) In the empty box, draw a complete curved arrow-pushing mechanism illustrating how the major product is formed. Be sure to include all arrows, intermediate structures, and formal charges.

(b) (10pts) Draw the structures of the 5 minor alkenes in the order of least to most stable. You may assume that a 6-membered ring is more favorable than a 5-membered ring.

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