CHEM 343 Quiz 5 1 How could the sythesis below be completed O O O a 1 Cl AlCl3 2 b 1 Cl AlCl3 c both a and b give the desired product Cl AlCl3 2 Cl AlCl3 d both give the desired product but choice a works better 2 Rank the following in order of increasing reactivity towards SN Ar OH N N N N O2N N I a III I II IV III II b I III IV II N c IV II III I N O2N Br N N IV d II IV I III 3 How could the synthesis below be completed Br NH 2 a 1 Br 2 FeBr 3 2 H 2SO 4 HNO 3 3 H 2 Pd C c 1 H 2SO4 HNO 3 2 Br 2 FeBr 3 3 H 2 Pd C b 1 H 2SO 4 HNO 3 2 H 2 Pd C 3 Br 2 FeBr 3 d any of the above 4 Which of the starting materials below should be used to make the desired product O SO 3H a SO 3H b O c O SO3H 5 In the reaction below N2 CN CuCN a The lone pair in nitrogen s sp2 orbital populates CN b The lone pair in carbon s sp orbital populates CN c Two CN electrons populate NN d The lone pair in carbon s sp orbital populates CC 6 Which of the following leads to the formation of benzyne a N2 c b 1 CuF 2 NaNH 2 N2 d a and b 1 Br 2 FeBr 3 2 NaNH 2 1 CuI 2 NaOH e a b and c 7 The reaction below was conducted with radioactively labeled oxygen indicated by the asterisk Which of the following is a possible outcome of the reaction O a HO OH b HO OH H H 2O c HO OH d a and b e a b and c 8 The product s of the reaction below is are SH a SH NO 2 H 2SO 4 HNO 3 SH b c O2N NO 2 SH d a and c 9 Select the correct statement regarding equilibrium constants K1 and K2 Reaction 1 O HO H 2O Reaction 2 O OH HO F H 2O F K2 K1 a K1 is greater than K 2 because the hydrate formed in reaction 1 is less stable b K 2 is greater than K1 because the carbonyl in reaction 2 is less electrophilic c K 2 is greater than K 1 because the carbonyl in reaction 2 is more electrophilic d K1 is greater than K 2 because the carbonyl in reaction 1 is more hindered 10 How could the reaction below be forced to run to the right O HO OH H H 2O a use excess acid b remove water c remove acid d use excess water OH
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