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A draw the structure of these three products and

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(a) Draw the structure of these three products and explain which product is favored and why. (b) For the two chiral products in part a, draw both enantiomers with appropriate labelling of the stereocenters. (c) Equivalent amounts of enantiomers must be formed in this reaction, though the relative amounts of the diastereomers can be different. Draw the two enantiomeric secondary cations and the four potential products in the boxes below. Indicate the enantiomeric pairs of products. CH 3 H HBr addition bottom HBr addition top enantiomeric secondary cation intermediates Br - attack bottom Br - attack top Br - attack bottom Br - attack top major minor minor Chem 33, Kanan & Stack, 2012, PS 6; pg 3
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(a) nucleophiles from weakest to strongest: Br , CH 3 Se , Cl (b) nucleophiles from weakest to strongest: (c) leaving groups from least to most reactive: (d) nucleophiles from weakest to strongest: CH 3 O , CH 3 OH, CH 3 NH 2 , CH 3 NH Br , Cl , F , I 6. Rank the following and succinctly explain. Br , Cl , F , I Circle the molecules that CN - will deprotonate Circle the molecules that H 3 O + will protonate Circle the molecules that NH 4 + will protonate OH O OH OH H H S - Br - O S - S - H 2 O HO CH 3 O - HS - Circle the molecules that will deprotonate O - O F F F SH OH O F F F OH O F H H OH O F F F 5. Acid & base comparisons are important when considering nucleophilic reactions. Assuming equal molar amounts of the specified and target molecules, circle the targeted molecules that will be significantly (~ 50%) deprotonated or protonated. If necessary, pKa values can be found in Table 2-2 in VS. Chem 33, Kanan & Stack, 2012, PS 6; pg 4
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8. Consider the SN2 reaction of CI - ( A ) with cyclohexyliodide ( B ) at 330 K in an aqueous solution. (d) If the initial concentration of both reactants are 0.01 M and the experimentally measured initial rate of disappearance of cyclohexyliodide is 1 x10 -8 M -1 s -1 , determine the second order rate constant for this reaction.
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