Problem_Set_5_Answer_Key

Problem_Set_5_Answer_Key - CH 3 Ph CH 3 h Ph CH 3 CH 3 For...

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Organic Chemistry c3046y Problem Set 5 - Amines, Pericyclic Reactions O OH NH 2 Ph NaNO 2 , H 2 SO 4 KBr 1. Predict the major product of the following reactions: a. b. OH Br 1. NaN 3 2. H 2 , Pd 3. NaNO 2 , HCl c. 1. Δ 2. H 2 NEt, H + , 2 equiv NaBH 3 CN HO HO Answer Key 1. NaN 3 OH N 3 2. H 2 , Pd OH NH 2 OH N 2 Cl O 3. NaNO 2 , HCl O OH Br Ph Ph O O via: HO HO 1. Δ OHC OHC Tautomerize N Et 2. H 2 NEt, H + , 2 equiv NaBH 3 CN
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2. Propose a synthesis to achieve the following transformation. OMe O MeO O NH 2 3. Provide a mechanism for the following transformation: R N 3 O Δ MeOH R H N O O Me NaOMe, MeOH I I MeO 2 C CO 2 Me H 3 O + CO 2 H O Cl SOCl 2 O Cl NaN 3 Δ , H 2 O R N O N N R N C O MeOH R N O O H Me R N O O H Me -H + , +H + 4. Predict the products of the following reactions, and provide mechanisms for their formation: O a. Δ O O Tautomerize O K + K + H 3 O + K +
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b. c. OH 1. Cl CH 3 O Et 3 N 2. LDA, Me 3 SiCl, Δ 3. H 3 O + Me Me OH O O Me CH 3 O Step 1 Step 2 O Me O SiMe 3 Me O O SiMe 3 Step 3
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Unformatted text preview: CH 3 Ph CH 3 h Ph CH 3 CH 3 For this one, we need to think about the reverse reaction (remember, it's an equilibrium favoring the butadiene form), which, under photochemical conditions, is dis rotatory. If it's disrotatory in one direction, then it's disrotatory in the other direction: Ph CH 3 CH 3 H Ph CH 3 CH 3 There is one other issue here, namely, that there are, in principle, two different disrotatory pathways. It stands to reason that the Ph and CH 3 groups will rotate away from each other as shown, and not toward each other, which would be the other possible disrotatory pathway....
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This note was uploaded on 04/16/2008 for the course CHEM C3046 taught by Professor Leighton during the Spring '08 term at Columbia.

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Problem_Set_5_Answer_Key - CH 3 Ph CH 3 h Ph CH 3 CH 3 For...

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