Unformatted text preview: Chem 51A Quiz 6 (10 points; 10 minutes) November 30, 2009 Academic Honesty Policy. Academic honesty is strictly enforced on quizzes, exams, and other aspects of this course.
Academic dishonesty will result in a failing grade in the class and a letter in the student's ﬁle. Activities constituting
academic dishonesty include: Cheating
'Copying from others during an examination. Communicating exam answers with other students during an examination. ~Offering another person's work as one's own. oTaking an examination for another student or having someone take an examination for oneself. -Tampering with an examination after it has been corrected, then returning it for more credit. °Using unauthorized materials, prepared answers, written notes, or concealed information during an examination. Dishonest Conduct
-Stealing or attempting to steal an examination or answer key from the instructor.
-Allowing another student to copy off of one's own work during a test. Collusion
-Any student who knowingly or intentionally helps another student perform any of the above acts is subject to discipline for academic dishonesty. I understand and will abide by this academic honesty policy: (signature) Seat: 1. (Smith 7 56a and 7 .62c, 4 pts)
a. Rank the following 1n order of 1ncreasing S N2 reactivity:_ C <__ <1) MMEM b. Rank the following 1n order of increasing SNl reactivity: b_q__ < @0”@ 2. Draw the product this SN2 reaction and indicate the stereochemistry. (Smith 7.580, 2 pts) />/\/Cl + 1301—120143 _. />/\/OCHI CK?
1H III/[H 3. Write a curved—arrow mechanism for the solvolysis of 2-chloro-2-(p-methylphenyl)propane in aqueous acetone to form
2-(p-methy1phenyl)-2-propanol. (Hint: The reaction involves water.) (3 pts) heat
CH3+©+CI —-> CH3’©+OH + HCI H2 O-acetone
2— chloro- 2-( (pmethylphenprropane 49+a._ ~> 494 + or
~——@-+—: -H + H 0 H a" 5—H 7‘ H30?
” (0" Her) On I ’
4. Propose a short synthesis of the following +compoLnd, beEg'inan only with compounds conta1n1ngf ve carbon atoms or
fewer and any organic or inorganic reagents that you require. (1 pt) MB!‘ 1’ l\)qCI\j "9 MGM é ”QBn)
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- Fall '07