CHM 3120 Assignment 1 rev

CHM 3120 Assignment 1 rev - 3 CO O O OCH 3 O + c) O EtO 2 C...

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CHM 3120 Assignment #1: 1) Synthesize the “syn” and “anti” isomers of the following molecule: Ph OH CH 3 2) Predict the major product in each of the following reactions: a) O O NaBH 4 b) O OEt 1) LDA 2) O H NBn 2 c) N H O H H + (cat.) d) O N H CH 2 Br 1) 2) 3) H + /H 2 O
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e) O 1) LDA, THF O 2) , H 2 O 3) NaOH, heat f) O Br t BuO - K + t BuOH g) TBSO O H OTBS + N O OLi O h) O O 1) Ph 2 CuLi, -78°C 2) H 2 O i) EtO O O OEt 1) NaOEt, 2) NaOH, H 2 O 3) HCl, H 2 O 4) heat O 3) Consider the following reaction: O 1) LDA, THF, -78°C 2) PhCHO a) Which is the MAJOR enolate? Why? b) What is the stereochemistry of the major product? Explain.
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4) Provide the missing reagents. (Hint: for c) you will need a second S.M.): a) O ? O Ph OH b) O Ph H ? Ph O H c) O OEt O O OEt ? 5) Provide the most logical starting materials for the products below. You do not need to include reagents: H O ? d) EtO O O ? a) O O ? b) O O O ? c)
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6) Suggest a synthesis of the following molecules from the given starting material. Include all necessary reagents. a) O EtO O O OEt b) O O H
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Unformatted text preview: 3 CO O O OCH 3 O + c) O EtO 2 C O CO 2 Et 7) Predict the stereochemistry of the major product in the following reactions: a) Ph O H EtMgBr THF b) O NaBH 4 H 2 O c) O tBu Ph Zn(BH 4)2 d) OLi O H 8) How would you prepare A from B ? O H O Br B A 9) Provide a plausible mechanism for each of the following reactions: a) O O Br Br 2 CH 3 CO 2 H b) O Ph Ph O NaOH heat c) O OH O O O OCH 3 HCl CH 3 OH 10) How would you use a Robinson Annulation to make the following compounds? a) N CO 2 Et O O b) 11) When 1,3-cyclohexanedione reacts with methyl vinyl ketone in the presence of sodium ethoxide, a mixture of two isomeric products having the formula C 10 H 12 O 2 are formed. Propose structures for the two products and write mechanisms for their formation. O O O NaOEt X + Y...
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CHM 3120 Assignment 1 rev - 3 CO O O OCH 3 O + c) O EtO 2 C...

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