Question

art (10) Answer at least 6 of the following 10 questions. You may answer extra questions, but a 2 point deduction will be asso ich extra incorrect answer. For those questions marked with an asterisk, a correct rank will earn you a 5 point bons. If you don't kn structure that is named you may buy it for a lpt deduction For questions marked with a sign a 3 point bonus will be wwanded correct product structure 1. Which compound is most acidie? 2. Which proton will give the peak shown below? The chemical shin is 2.22 ppm and J - 6.9 +3. Which compound will form a five membered ring product? он во NH 4. Which substance is consistent with the following "H-NMR spectrum (below left? Only the aromatic peaks are shown. (A) 2-bromaanilise (B) -bromaaniline (C) 4-bromoaniline (D) 2.4-dibromaniline +*5. Which compound reacts most rapidly with dimethylamine? "Olgich, gli 6. Which compound is the strongest acid? (Hint: Draw the conjugate base before reaching a decision.) 00 оси, 00 +7. Which compound is not likely to form a product upon reaction with the sodium enolate from diethyl malonate? Draw products for the reactions that do work for 3 pt bonuses. Write N. R. for the reaction that doesn't work. 8. Which product results when ethyl acetoacetate is treated with the following reagents in the sequence indicated? 1. LDA eq) IL CH, 2. CHI (1 eq) 1. strene oxide (leg) (B) 4. LDA (2 ) 5. CH CH I (1 eq) 6. CD, (1 eq) Ico TT OLED

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Answer 1

1. D (the coresponding phenoxy group stabilized by -R group present in ortho position)

2. Hc (Apply n+1 rule)

3. D

4. A

5. D ( when amine attack to carbonyl group the coressponding leaving gr must be stabilized, in this case the leaving group is most stabilied because it forms equivalent resonating structure)

6. C ( conjugate base is more stabilized due to resonance -ve charge can be stabilized by three electron withdrawing group)

7. A (Na enolate attack to more electrophilic centre)

8. D