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3. Rank these six ions/molecules in order of increasing leaving group ability (1 good, 6 poor) Remember that the weakest bases make the best leaving groups. (2.5 pts) 4. Three of the four reactions below contain a significant problem or error. Choose the letter (a statement that best describes the problem or error. write OK: Evaluate only whats written on this page: do not consider missing curved arrows, missing lone - f) of the If nothing is wrong. Do not use a letter more than once. pairs, or missing reactants/products. (2 pts) Cl NH CH3 Насе CH3 NaN3 DMSO 3 S1 (a) poor leaving group (b) incorrect stereochemistry (c) curved arrows drawn improperly () alkyl halide too sterically hindered (d) thermodynamically unfavorable rearrangement (e) nucleophile too weak
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4 6 1 is neutral therefore it is the weakest base. In 2 and 3, the negative charge is delocalized. Between 2 and 3, 2 has electron withdrawing -CF3 group. Thus, i is a weaker base among the two. Among 4, 5 and 6 the electronegativity of O> N> C. The electronegative atom hold on to electrons tighter making electron donating ability of the groups poorer. Therefore, among the three, 4 is the weakest base and 6 is the strongest base. The weaker the base, the better is its leaving group ability

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