prac mid 3

prac mid 3 - Chemistry 140A Professor Nathan Gianneschi...

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Unformatted text preview: Chemistry 140A Professor Nathan Gianneschi Winter 2009 Chapter 7-9 Practice Midterm March 18th, 2009 Name:............................................... First Last Signature:....................................... PID#:.............................................. 1. [6 pts] k1 and k2 are approximately equal for the two reactions shown below despite one being primary and one being secondary. Draw resonance structures to explain this observation. Br Br k1 k2 2. [6 pts] Give the rate equation for an SN1 reaction occurring between H2O and a tertiary alkyl halide, RX. Write your answer in the box below. 3. (a) [6 pts] In the box provided below indicate the product if complete racemization has occurred. H3CH2C H3 C C Cl H2O Ethanol (H3C)2HC(H2C)3 (b) [4 pts] If ion pairing effects are accounted for, which enantiomer would you expect would be found in higher yield? Write S or R in the box provided. 4. [38 pts] Propose a synthesis for the compound in box 3 below. Make it in TWO steps from starting materials of 4 carbons or less. HINT: You are going to have to make a new carbon-carbon bond. 1 2 3 OH 5. [40 pts] Fill in all structures in the boxes provided for the reaction scheme indicated. Remember to look at the formulas provided to help you. Appropriate work ups are assumed when not indicated. PBr3 Ether LiAlH4 O Diethylether O H C6H13OBr Mg C6H14O2 15% H2SO4 t-BuOH 40oC, -H2O O 1) Diethyl ether O OH 2) H+/H2O C6H13OMgBr 1) H2SO4 50oC 2) NaH, THF C5H10O C9H19OCl SOCl2 CH2Cl2 C2H4O2 ...
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prac mid 3 - Chemistry 140A Professor Nathan Gianneschi...

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