Assignment 22-3 - 5 C O CH 3 C O O C O C 2 H 5 O C O CH OC...

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Organic Chem 2 Name________________________ Assignment 22-3 1. Predict the organic product(s): O C OC 2 H 5 (A) 2 CH 3 CH 2 H + O C Na + OC 2 H 5 - OC 2 H 5 HOC 2 H 5 H 2 O O C CH 3 CH 2 (B) OC 2 H 5 + H H + Na + OC 2 H 5 - HOC 2 H 5 H 2 O (C) O C OC 2 H 5 CH 3 + O C OC 2 H 5 H + Na + OC 2 H 5 - HOC 2 H 5 H 2 O (D) CH 3 O CH 3 C O C OC 2 H 5 + H H + Na + OC 2 H 5 - HOC 2 H 5 H 2 O (E) O C OC 2 H 5 CH 3 CH 2 + C 2 H 5 O O OC 2 H 5 C Na + OC 2 H 5 - HOC 2 H 5 H + H 2 O Na + OC 2 H 5 - HOC 2 H 5 H + H 2 O (F) O + H + H 2 O (G) C 6 H 5 CH 2 O C OC 2 H 5 Na + OC 2 H 5 - HOC 2 H 5 O C OC 2 H 5 O C O OC 2 H 5 C C 2 H 5 O + (H) CH 3 CH 2 O CH 2 CH 3 C LDA THF CH 3 CH 2 -Br (I) CH 3 O CH 2 C O C OC 2 H 5 Na + OC 2 H 5 - HOC 2 H 5 CH 3 -Br CH 2 O C OC 2 H 5 O C C 2 H 5 O (J) Na + OC 2 H 5 - HOC 2 H 5 C 6 H 5 CH 2 -Br (K) O LDA THF CH 3 CH 2 -CH 2 Br CH 2 CH 2 CH 2 CH 2 O C OC 2 H 5 O C C 2 H 5 O (L) H + H 2 O Na + OC 2 H 5 - HOC 2 H 5 [Hint: product is cyclic]
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CH 3 CH 2 C O OC 2 H 5 N. LDA THF O LDA THF O P Q CH 3 C O CH 2 C O CH 3 CH 3 -C O CH 2 Br Br CH 3 CH 2 Br C O OC 2 H 5 M NaOC 2 H 5 HOC 2 H 5 CH 3 -I NaOC 2 H 5 HOC 2 H 5 C 6 H 5 -CH 2 -Cl LDA THF O See next page for answers
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ANSWERS: OC 2 H 5 C O CH 3 CH 2 C O CH OC 2 H 5 C O CH 3 C O H CH OC 2 H 5 C O CH 3 C O OC 2 H 5 C O CH 2 C O H C O CH 3 CH 2 C O C 2 H 5 O CH
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Unformatted text preview: 5 C O CH 3 C O O C O C 2 H 5 O C O CH OC 2 H 5 C O C 6 H 5 C O CH 3 CH 2 CHCH 3 CH 2 CH 3 OC 2 H 5 C O CH CH 3 CH 3 C O OC 2 H 5 C O CH CH 2 C O CH 3 O C 6 H 5 O CH 2 CH 2 CH 3 O (A) (B) (C) (D) (E) (F) (G) (H) (I) (J) (K) (L) 1. CH 3-CH-C-OC 2 H 5 O P M N. O O. Q CH 3 C O CH C O CH 3 CH 2 C 6 H 5 CH 3-C O CH C O OC 2 H 5 CH 3 CH 2 CH 3 O...
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