pp. but-1-en-3-one + NaCN 1. React the carbonyl compound: It is (circle one) CONJUGATED NON-CONJUGATED The Nucleophile is Resonance System :0 8- pi Option 1: Only the Nu created from RMgBr, NaBH or LIAIH sticks R-CH CH Option 2 All other Nu end up here eventually 1 (Preferred) NUB Circle the option and reason Option 1: RMgBr, LIAIH4, or NaBH4 Option 2: All other Nu end up sticking here 2. Take care of the negative formal charge of the oxygen in the tetrahedral complex Option 1 (Preferred): All cases except Option 2 1 (Preferred) Option 2: If there are no leaving groups, R- or if the only potential leaving group is the Nu that was just added and it is not a very good leaving group (N or O). Circle the option and reason Option 1: Always use UNLESS Option 2: There is no leaving group (there are only carbons and hydrogens), OR there are only carbons and hydrogens except for the Nu that just added, AND the Nu is N or O. If the double bond is reformed, what criterion is used to select the leaving group? (circle one) Shells Electronegativity EWA/Resonance Charge 3. If a hydrogen atom is added instead, does the reaction continue? Yes No Xs or 8- H0-H R -C- -R 8- Nu

pp. but-1-en-3-one + NaCN 1. React the carbonyl compound: It is (circle one) CONJUGATED NON-CONJUGATED The Nucleophile is Resonance System :0 8- pi Option 1: Only the Nu created from RMgBr, NaBH or LIAIH sticks R-CH CH Option 2 All other Nu end up here eventually 1 (Preferred) NUB Circle the option and reason Option 1: RMgBr, LIAIH4, or NaBH4 Option 2: All other Nu end up sticking here 2. Take care of the negative formal charge of the oxygen in the tetrahedral complex Option 1 (Preferred): All cases except Option 2 1 (Preferred) Option 2: If there are no leaving groups, R- or if the only potential leaving group is the Nu that was just added and it is not a very good leaving group (N or O). Circle the option and reason Option 1: Always use UNLESS Option 2: There is no leaving group (there are only carbons and hydrogens), OR there are only carbons and hydrogens except for the Nu that just added, AND the Nu is N or O. If the double bond is reformed, what criterion is used to select the leaving group? (circle one) Shells Electronegativity EWA/Resonance Charge 3. If a hydrogen atom is added instead, does the reaction continue? Yes No Xs or 8- H0-H R -C- -R 8- Nu

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter8: Addition Via Carbocation

Section: Chapter Questions

Problem 31CTQ

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