To be clear: once tutor is matched i will attach document containing the problem set. Once document is sent it must be returned no more than 2 hrs later. Due at 12 AM EST. Answers to all the questions in the problem set (multiple choice and free response). Topics covered are: Multi step synthesis Radical reactions Electrophilic aromatic substitution Nucleophilic aromatic substitution 1. Produce a retro synthetic analysis 2. Calculate overall yield for a reaction 3. Classify a reaction by reaction type 4. Identify the steps of a radical chain mechanism 5. Provide the starting materials reagents conditions products and mechanism for the following reaction (If we skipped the mechanism in class then you are not expected to know the mechanism): a. Free radical halogenation of alkanes b. Free radical halogenation of alkenes c. EAS halogenation d. EAS nitration e. EAS sulfonation (and reverse) f. Friedel Crafts alkylation g. Friedel Crafts acylation h. Benzene hydrogenation i. Nitro to amine j. Alkyl benzene to benzoic acid k. Diazotization l. Sandmeyer reactions m. Nucleophilic aromatic substitution n. Benzyne reactions 6. Identify the key steps of an electrophilic aromatic substitution reaction 7. Identify groups as o/p or m directing 8. Identify groups as activating or deactivating 9. Provide a viable multistep synthesis for a substituted benzene molecule Why a particular forward synthesis or retrosynthesis is viable or not. 2. The differences between a homolytic process and a heterolytic process 3. What happens in the key steps of a radical chain reaction 4. Which conditions favor heterolytic or homolytic processes and why 5. What happens in each step of an electrophilic aromatic substitution reaction. 6. Limitations of Friedel Crafts reactions 7. Why a group is an o/p or m directing group 8. Why a group is an activating or deactivating group Requirements: As indicated by each individual question. Multiple choice = no work needed. Free response may include mechanisms but the level of detail is specified by each question. ‘
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