Problem_Set__1_solutions - + HO — H 2 We will later learn...

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Chem 358 Spring 2007 Problem Set #1 Answers to Additional problems 1. Write down all the possible resonance structures for the initially formed allylic carbocation. Identify those with β -hydrogens that can be eliminated to form a carbon-carbon double bond and write down the structures of the corresponding elimination products. Note that only the tertiary allylic carbocations give elimination products. The primary and the secondary ones do not have the appropriate hydrogens to eliminate. OH H + Vitamin A (Retinol) H H H H H H H H H H H H H + —H + —H + —H +
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2. CN CN H O CN NC (a) + CN CN Heat trans substituents H O O + H O Heat OCH 3 OCH 3 O O cis cis trans OCH 3 OCH 3 O O + OCH 3 OCH 3 O O Heat (b) (c) 3. OH Cl Ci + Retrosynthetic steps Ci + Cl HO OH Heat The proposed synthesis
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Unformatted text preview: + HO — H 2 We will later learn better ways of making alcohols, such as making them from either aldehydes or esters. 4. O O CH 3 O + O O H CH 3 O Several characteristics of the Diels-Alder reaction are illustrated by this. (1) Only the methyl-substituted double bond reacts. The methoxy-substituted one is too electron-rich. (2) The cis ring fusion retains the stereochemistry of the double bond in the dienophile. (3) Further cycloaddition of diene to the product does not occur because the double bonds in the product are not sufficiently electron-deficient to react at an appreciable rate....
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This note was uploaded on 04/22/2009 for the course CHEM 3570 taught by Professor Ganem, b during the Fall '06 term at Cornell University (Engineering School).

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Problem_Set__1_solutions - + HO — H 2 We will later learn...

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