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test 1 blue answers - CHM 3120 Test#1 Blue Version 1...

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CHM 3120 Test #1 Blue Version 1. Consider the following reaction: 7 Points O Base a) Identify the kinetic product O 1 b) Explain why this is the kinetic product (point form) CH 3 H’s more acidic than CH Me 3 H’on Me – more likely to remove than 1 H on CHMe Me less crowded – easier for base to remove H than H on CHMe (3) c) Give reaction conditions that favor this product (point form) (give 3 to get 3 points) Strong, hindered base (LDA) Aprotic solvent (THF) Excess base Low temperature (-78 °C) Add carbonyl compound to base (3) 2. Draw structures for the unknown compounds. 8 Points . H N O O HOAc C 10 H 18 NO H 3 O+ C 12 H 14 O 2 C 17 H 24 NO Cl C 10 H 17 NO K 2 CO 3 O N 2 O N 2 O N 2 O O 2 3. Draw reaction pathways to the possible products. Identify the products (stereochemistry only). Predict the major product. Indicate the destabilizing interaction disfavoring the minor isomer. 15 points
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2 O Bn O O O H Bn O O O H O Bn O BH 4 - O H H Bn OH O O H H HO Bn O OH O O OH O O BH 4 - Newman 2 Configuration 2 Newman 2 1 1 1 1 2
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