HW06Key - the target compound from the indicated starting...

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Bocknack CH 310N Spring 2010 Graded Homework Assignment #06 – Answer Key Deadline : 2:00 p.m., Friday, 2/12/10 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This assignment is worth a total of 40 raw points. Consider the reaction scheme below to answer Questions 1 through 3: 1. (5 points) Propose a structure for Compound A . Write your answer in the box above. 2. (5 points) Propose a structure for Compound B . Write your answer in the box above. 3. (15 points) In the space below, propose a mechanism for the reaction that converts the epoxide into Compound B . As in any organic reaction mechanism, use curved arrows to show movement of pairs of electrons. Be sure to draw structures of all important reaction intermediates. O H 3 C H 3 C 1) CH 3 CH 2 MgBr, ether 2) H 3 O + m CPBA A B C C H 3 C H 3 C H H HO H 3 C H 3 C O H 3 C H 3 C Mg Br CH 2 CH 3 O CH 2 CH 3 H 3 C H 3 C MgBr H O H H HO CH 2 CH 3 H 3 C H 3 C H O H
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Bocknack CH 310N Spring 2010 2 4. (15 points) Propose a sequence of reactions to synthesize
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Unformatted text preview: the target compound from the indicated starting material(s). You may use any other organic and/or inorganic reagents necessary to complete your synthesis, but all carbon atoms in the target must be derived from the starting materials specified. It is only necessary to give overall transformations in answering this question. It is not necessary to provide complete curved arrow mechanisms for the reactions that you use. Prepare TARGET from and HC CH CH 3 CH 2 CH 2 CH 3 Cl H H Cl CH 3 CH 2 Br and CHCl 3 All C atoms in the target must originate in these starting materials! HC CH CH 3 CH 2 CH 2 CH 3 Cl H H Cl 1) NaNH 2 2) CH 3 CH 2 Br HC CCH 2 CH 3 1) NaNH 2 2) CH 3 CH 2 Br C C CH 3 CH 2 CH 2 CH 3 H 2 Lindlar cat. C C CH 3 CH 2 CH 2 CH 3 H H KO t Bu CHCl 3...
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This note was uploaded on 04/07/2010 for the course CH 310n taught by Professor Iverson during the Spring '08 term at University of Texas.

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HW06Key - the target compound from the indicated starting...

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