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week6_questions - Chemistry S-20 Week 6 Amine Basicity 1...

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Amine Basicity N NH C N N N N Cl CH 3 CH 3 N N N N Me 2 N 1. Rank each of the following sets of nitrogen bases in terms of basicity, and explain your ranking: H 2 NNH 2 NH 3 HONH 2 N N N CH 3 CH 3 Chemistry S-20 Week 6 188
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Amine Synthesis: Reagents 1. 2. 1. Each of the following transformations can be carried out in one to three steps. Fill in the reagents required for each step. 1. 1. 2. 1. 2. Br NH 2 O HN O Cl N O 2. HO NH 2 1. 2. NH 2 3. 3. 3. 3. 3. Chemistry S-20 Week 6 189
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Br CN OH Br Br CH 3 Br Aryl Diazonium Salts CH 3 1. Propose a synthetic pathway for each of the following targets starting from benzene or toluene . Each synthesis will require the use of an aryl diazonium salt as a key step. Chemistry S-20 Week 6 190
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Aryl Diazonium Salts: Synthesis 1. Provide a multistep synthesis for the desired product from the indicated starting material. You may use any inorganic reagents. The best answer will require six or fewer steps. Br Br Starting material: Desired product Chemistry S-20 Week 6 191
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O Beckmann and Curtius Rearrangements 1. Provide the intermediates and products for the following transformations, and write a curved-arrow mechanism for the crucial rearrangement step. Cl O NH 2 OH NaN 3 NaOCH 3 H + Chemistry S-20 Week 6 192
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Hofmann Rearrangements 1. Write a curved-arrow mechanism and predict the product for this reaction. Cl O 1. Br 2 , NaOH NH 3 2. H + , H 2 O Chemistry S-20 Week 6 193
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Putting It Together: Reagents 1. Each of the following transformations can be carried out in one to three steps. Fill in the reagents required for each step. Cl O H N 2. 2. 1. 3. 2. 1. 1. 1. 3. 3. 2. 3. Cl O NH 2 1. 2. 3. 1. 2. 3. O O OH O O O O NH 2 C O OH O H Chemistry S-20 Week 6 194
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H O N H H 3 C CH 3 H O N The Mannich Reaction HN O 1. Provide a curved-arrow mechanism for the following transformation. N O pH 5 CH 3 CH 3 Ph + 2. Show how a Mannich reaction can be used to complete the following synthetic transformation. ??? Chemistry S-20 Week 6 195
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O N Me NH 2 N O NH 2 O NMe 2 Putting It Together: Synthesis of Amines NHMe Using cyclohexanone as your starting material, show how you could synthesize the following amines: O O O O O O NH 2 Chemistry S-20 Week 6 196
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O NH O Me Putting It ALL Together: Synthesis 1. Provide a synthetic pathway for each of the following multistep transformations. N H Chemistry S-20 Week 6 197
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Extra Practice 1. Provide a multistep synthesis for the desired products from each indicated starting material.
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