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Midterm2007 - B Provide a detailed mechanism describing...

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CHM 3120 Intermediate Organic Chemistry (Fall 2007) EXAM#1 Instructions: Please answer all questions in the space provided. If you require additional space use the back pages. Model kits are permitted. There are 5 questions plus a BONUS question. Time allotted: 3 hours 1 . Predict the product(s) from the following reactions. Be sure to show relevant stereochemistry where required. (15 points) NaOH/H,0 Ph heat W k 00 •1. 0 f) PhO 9) 0 NaOEt/EtOH OCH 2 CH 3 0 1)PhSH 2) H 3 0 + o
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3. a) Consider the following reaction. What is the structure of the major product in this reaction? Draw the transition state for the major product. The minor product is formed via a different transition state. Draw the transition state for the minor product also. (5 points) b) Consider the following reaction. Draw the structure of the major product and rationalize formation of the major product using the appropriate transition state. (5 points) Zn(BH 4 ) 2 OH .'OH • ' . SCH-,
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' 4. Consider the following reaction. What are the structures of intermediate A and product B? Provide a detailed mechanism describing formation
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Unformatted text preview: B? Provide a detailed mechanism describing formation of intermediate A. (10 points) o H H 3 O + , heat o ! : 1)CH 3 2) H 3 + o I/ 5. Consider the following molecule. Provide a multistep retrosynthesis (i.e. making logical bond disconnections backwards) for C starting from D and any other starting materials you require. (10 points) 0 0 OEt ~ ' t 0 Nf,ol4/tt x O G£t 0 0 Bonus Question! Predict the structure of the product in the following reaction. Draw a transition state that explains how this product is formed. (2 points) 0 0 A, 1)LDA, THF-78 °C 2) CH 3 I o o r KA Name: Student #: t 2. Predict the major product from the following reaction. Draw the transition state that leads to the formation of this product. Draw the structure of the enolate formed in this reaction. (5 points) Si66S fir 0 LDA, THF Ph-78 °C o-1 j V , Ph 2) H 3 + °« (PK--PH '«j...
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