Assignment_6_Answers

Assignment_6_Answers - CHM 1321 Assignment #6 - ANSWERS In...

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CHM 1321 Assignment #6 - ANSWERS In this assignment: - Nucleophilic addition to carbonyls - Elimination reactions (E1, E2) To be covered the week of March 24 th 1) Give the products of the following reactions and give mechanisms to show how they are formed: B(OR) 3 B(OR) 3 H 3 CO H OH H H 3 CO H O H O H 3 CO H O O H OH H BH 3 H BH 3 H H 3 CO H O H B(OR) 3 H H 3 CO H O H H O H B(OR) 3 H H O H BH 3 H BH 3 H H 3 CO H O H BH 3 H 3 CO H O H B(OR) 3 H O H BH 3 H O H B(OR) 3 a) b) 1) NaBH 4 2) H 3 O + 1) NaBH 4 2) H 3 O + repeat 3X repeat 3X R R O O BH 3 H B(OR) 3 OH O H B(OR) 3 O H H BH 3 H BH 3 O H B(OR) 3 O H c) 1) NaBH 4 2) H 3 O + repeat 3X R
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Assignment 6 - ANSWERS 2 O O OH OH d) e) 1) NaBH 4 2) H 3 O + 1) NaBH 4 2) H 3 O + H BH 3 BH 3 H B(OR) 3 repeat 3X O O O BH 3 O B(OR) 3 O B(OR) 3 H OH H BH 3 BH 3 H repeat 3X O O BH 3 O B(OR) 3 O B(OR) 3 H OH O R R
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Assignment 6 - ANSWERS 3 O O OH OH f) g) 1) MeMgBr 2) H 3 O + 1) MeMgBr 2) H 3 O + O MgBr Me O MgBr O MgBr H O MgBr H H 2 O OH O MgBr Me O MgBr O MgBr H O MgBr H H 2 O OH
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Assignment 6 - ANSWERS 4 2) Predict the major products of the following reactions. a) b) c) d) e) Br Mg Et 2 O Cl Mg Et 2 O A B CH 3 OH Br Mg Et 2 O A B O Br Mg Et 2 O A B O Cl Mg Et 2 O A B O f) Br Mg Et 2 O A B O MgBr MgCl H MgBr OMgBr MgBr OMgBr MgCl OMgCl MgBr OMgBr
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Assignment 6 - ANSWERS 5 3) The following reactions would not work as shown. Explain why (look for a more favorable reaction that would occur instead). a) 1) Mg 2) 3) H 3 O + H O OH b) Br O 1) Mg 2) 3) H 3 O + H O O OH c) O 1) CH 3 CH 2 MgBr 2) H 3 O + Br HO O OH MgBr O Br H acid-base reaction would destroy the nucleophile. O Br BrMg H H H Mg Mg BrMg O Grignard reagent would react with another molecule of starting material instead of "waiting" to react with the aldehyde Br O Br OMgBr O H MgBr O OMgBr H acid/base reaction faster than Grignard reaction
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Assignment 6 - ANSWERS 6 4) Give all the different carbonyl starting materials and the Grignard reagent or reducing reagent that could be used to form each of the following compounds. OH H H O MgBr OR H O NaBH2 OH H O MgBr O OR BrMg OR O NaBH 4 OH O OR O BrMg CH 3 BrMg O a) b) c)
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Assignment 6 - ANSWERS 7 5) Name the following compounds a) b) c) d) e) f) g) 6-methylheptene or 6-methylhept-1-ene 2-ethylpentene or 2-ethylpent-1-ene 4-methylhepta-1,6-diene 4-vinylcyclohexene 3(S),4(R) -dimethylcyclopentene E -2-methyloct-4-ene 5Z -2,7-dimethylocta-1,5-diene *Don't forget to specify the stereochemistry!
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Assignment 6 - ANSWERS 8 6) Predict the products of E1 elimination for the following compounds. Predict the relative amounts of each product.
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Assignment_6_Answers - CHM 1321 Assignment #6 - ANSWERS In...

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