week4_questions

week4_questions - NO 2 Cl O O CH 3 CH 3 O OCH 3...

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Unformatted text preview: NO 2 Cl O O CH 3 CH 3 O OCH 3 Electrophilic Aromatic Substitution: Direction NO 2 1. For each of the following species, show the most likely site(s) for electrophilic aromatic substitution, and predict whether the molecule is more reactive than benzene or less reactive than benzene. Chemistry S-20 Week 4 115 1. 2. 1. Each of the following transformations can be carried out in one or two steps. Fill in the reagents required for each step. If a second step is not needed, please put an "X" through the second box. 1. 2. 1. 2. 2. 1. 2. 1. OH O Cl CH 3 CH 3 NO 2 O O Electrophilic Aromatic Substitution: Reagents O Chemistry S-20 Week 4 116 HN O CH 3 Cl HN O CH 3 Electrophilic Aromatic Substitution: Mechanisms 1. Provide a curved-arrow mechanism for the following transformation. Show resonance structures for the cationic intermediate which make it clear why the substitution goes where it does. AlCl 3 catalyst 2. Provide a curved-arrow mechanism for the following transformation. O + H 2 SO 4 catalyst Chemistry S-20 Week 4 HN O CH 3 Cl HN O CH 3 Electrophilic Aromatic Substitution: Mechanisms 1. Provide a curved-arrow mechanism for the following transformation. Show resonance structures for the cationic intermediate which make it clear why the substitution goes where it does. AlCl 3 catalyst 2. Provide a curved-arrow mechanism for the following transformation. O + H 2 SO 4 catalyst Chemistry S-20 Week 4 117 CH 3 H 3 C OH Electrophilic Aromatic Substitution: Mechanism CH 3 CH 3 1. Provide a complete curved-arrow mechanism for the following transformation. H 2 SO 4 Chemistry S-20 Week 4 118 Introduction to Multistep Synthesis O Br Now that you know many organic reactions, it is possible for you to attempt more complicates multistep syntheses. For these syntheses, it is crucial that you learn to work backwards from the desired target. This requires you to examine the functional groups in the target molecule and ask: what reactions do I know that can synthesize that functional group? 1. Consider the following synthetic target. Working backwards from this target, there are at least five possible immediate precursors to this target. Find five possibilities, and evaluate each one to see if it makes sense. Now , before your next section meeting, take the two most promising routes and devise a complete synthesis of the above target starting with benzene and any compounds with 4 or fewer carbons . Chemistry S-20 Week 4 119 Introduction to Multistep Synthesis O Br 1. Given the work you did on the previous page, design a complete synthesis of the target material starting from benzene and any other reagents containing 4 or fewer carbons. Chemistry S-20 Week 4 120 OCH 3 OCH 3 Br OCH 3 Br Br Br 1. The following reaction produces a mixture of the two products A and B : a) Provide a complete curved-arrow mechanism that leads to the product A....
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week4_questions - NO 2 Cl O O CH 3 CH 3 O OCH 3...

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