Organic Chemistry CHE230-001 Key EXAM 2 Page 1 of 4 1) OSOOCF3HpKa = -12 Given the pKa of the acid to the left, answer the following questions. a. (10 pts.) Draw two possible elimination products of molecule 1A. OSOOCF3elimination+1AH40 °C in acetic acid b. (5 pts.) Does molecule 1B eliminate at the same rate as molecule 1A? Briefly justify your answer. Credit will only be given if you provide a reason for your answer. ___No, they are diastereomers________ _Diastereomers have different ______ _ rates of reaction ____________________ ______________________________________ c. (10 pts.) Draw product 1cb of the reaction below, it has ten 13C NMR signals. Pay attention to stereochemistry! Give 7 points if no stereochemistry or the wrong stereochemistry in the substitution product. Give 5 points for an elimination product. d. (10 pts.) In 1ca, the carbon atom bonded to CH3 is stereogenic. What is its absolute configuration in terms of R or S? ___S___ What is the absolute stereochemistry of the other stereogenic carbon atom in 1ca? __R____ OSOOCF3H1BOSOOCF3CCH3CONthis is thesolvent1caLi-30 °C 1cbOrganic Chemistry CHE230-001 Key EXAM 2 Page 2 of 4 2) (45 pts.) Fill in the blank(s) with any or all of the following letters. a. (5 pts.) __A-E, or all, ___ are isomers. b. (5 pts.) ___A, C, _ is (are) meso molecule(s). (don’t subtract pts if D) c. (5 pts.) ___A, C, D___ are achiral. d. (5 pts.) ___A, B, E____ are stereoisomers. e. (5 pts.) ___B, E___ are enantiomers. f. (5 pts.) _A, B or A,E__ are diastereomers (select only one pair). g. (5 pts.) _A_____ has (have) axial and equatorial groups. h. (5 pts.) __B, C, E__ has (have) two groups in equatorial positions. i. (5 pts.) ____B, E___ are molecules with identical properties. 3) The year is 3050 AD. The namuh are aliens from another planet. We humans are their enantiomers on the biochemical level. 3a (5 pts.) A human offers a numah three mind-altering substances. Ecstasy, mescaline and psilocybin. She is considering two and avoiding one; which one? _3A, ecstasy__ Why? ___The alien would be taking a risk with ecstasy, she does not know what it will do because it is chiral and will form a diastereomeric pair with her biochemistry_ 3b (5 pts.) You are lucky enough to date a gorgeous Numah. The relationship deepens and you marry. The loving is good, but can you have children? _NO__, Why or why not? All the biomolecular mechanisms and molecular interactions would be diastereomeric to the ones that work. So they would not work successfully. 4) (10 pts.) Draw the structure of product 4B. 7 pts. for an stereo undefined molecule. 5 pts for an elimination product.
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