CHEM 343 Quiz 9 1 The product of the reaction below is O a 1 NH 2OH trace H 2 LAH H work up b NH 2 c d H N NHOH H N OH 2 Select the appropriate set of starting materials and conditions to complete the reaction below O a b O O 1 PBr 3 Br 2 HO c HO HO 2 EtBr 3 H 2O O O O 1 NaOEt EtBr 2 H H 2O OH d EtO O 1 NaOH MeCl 2 1 NaOEt EtCl 2 H H 2O O EtO OEt 3 Select the conditions to complete the reaction below O O a LDA 78o then Br b NaOMe R T then Br c LDA R T then Br d either b or c 4 Which of the bases below could be used to make exclusively a kinetic enolate a Si Li N b NaNH 2 Si c OK d a and b e a and c 5 Which of the following has the greatest enol content at equilibrium a b O O O c O d O OH 6 What is the product of the reaction below O MeO a 1 NaOMe MeI 2 H H 2O O OMe b O O c O HO d O MeO HO OH O O OMe 7 How could the reaction below be completed O O OH a 1 mCPBA 2 H H 2O b NaOH I 2 H work up c both a and b d neither a nor b 8 Given the intermediate below what is the product of the reaction H 2O a b O N c a mixture of a and b O N H N H 9 Select the correct statement regarding the reaction below H O NH 2OH a The oxygen adds to the carbonyl carbon because it is more partially negative b The oxygen adds to the carbonyl carbon because its lone pair is closer in energy to CO c The nitrogen adds to the carbonyl carbon because it is more partially negative d The nitrogen adds to the carbonyl carbon because its lone pair is closer in energy to CO 10 Which carbon would be deprotonated if NaOMe were added to the molecule below O 2 1 3 Br a carbon 1 because it is more accessible b carbon 2 because the hydrogens are more acidic c carbon 3 because its conjugate base is more stable d cannot be determined
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