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1. Some questions of organic chemistry 2 lab, reduction of reduction of fluorenone with NaBH4. 

Detailed info is attached. 

2. How can you determine if there is pi bond in NMR spectrum? 

CHEM 242– Reduction of 9-Fluorenone Post-lab Questions Post-lab Questions: Answer these post-lab questions neatly and concisely on the back of the lab report sheet. Use a blank sheet of paper if more space is needed to answer these questions. Your answers will be evaluated and graded on quality, not quantity of response! You are to complete this post-lab questions assignment individually. You should work on this post-lab questions assignment as you would work on a take-home examination. Write all responses in ink. Responses written in pencil [in part or whole] will be accepted for a grade, but ANY and ALL requests for a regrade will be denied. This also applies to responses written in pencil and then overwritten in ink and/or responses obliterated with white-out-type materials and then revised. Post-lab Question #1: Consider the triketone shown below. O O O a) If a sample of NaBH 4 is 70% pure by mass (the remaining 30% is incapable of reducing carbonyls or reacting with the reactant or product), what is the minimum mass of the NaBH 4 sample required to fully reduce 8.26 g of the triketone above? (3 points) b) How many stereoisomers of the product triol would be formed? How many pairs of enantiomers would there be? How many pairs of diastereomers would there be? (2 points) c) If there is no molecular symmetry/meso issues (as is the case above), then if there are n stereoisomers, there are n/2 pairs of enantiomers. Derive a formula that is a function of n that will provide the number of pairs of diastereomers for all stereoisomers if there are no symmetry/meso issues. (3 points) Post-lab Question #2: Fluorenone can be synthesized from fluorene by reaction with NaOH in the presence of oxygen and a catalyst. The first step of the reaction is deprotonation of fluorenone. CH bonds normally have a pK a in the 50+, but the pK a of fluorene is estimated to be 22-23 in dimethylsulfoxide.
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a) Which hydrogen of fluorene is deprotonated by NaOH? (1 point) b) Why is fluorene so easy to deprotonate compared to a “normal” CH bond? Justify your answer appropriately. (2 points) Some thoughts on answering post-lab questions In many of the post-lab questions, you will be asked to provide an answer and an explanation for that answer. In the past, many students have written prose explanations. When you are writing your explanations, you should seriously think about explicitly including a chemical structure(s) and or a chemical equation(s) in addition to the prose as part of your explanation. Chemical structures and/or chemical equations can be used to add a great deal of specific information to an explanation in a way that pure prose cannot. In addition, chemical structures and/equations can make your responses much each easier to understand. When you are writing your explanations for the post-lab questions, make sure you include all necessary information. Do not answer a post-lab question with the assumption …I don’t have to include that, the TA will know what I mean. The TA can evaluate and grade only what you have written, not what is not there. Audience: Even though a TA will evaluate and grade your post-lab question responses, you should answer the post-lab questions as if you were providing that explanation for a fellow organic chemistry I laboratory student. If a fellow organic chemistry I laboratory student does not understand your explanation, then you need to provide more specific information and/or rewrite your response in a more understandable manner.
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