H our Examination #2, Chemistry 302-302A, 2004 "Problems worthy of attack prove their worth by hitting back." Piet Hein (thanks to Josh Schulman) 1 (21 points). Devise syntheses for the following molecules. You may use any inorganic reagent, alcohols cont
Hour Examination #3, Chemistry 301X - December 14, 2006, 7:30-10:00 pm Theres nowhere to run, nowhere to hide. Martha and the Vandellas 1 (20 points). In answering Group Problem 85, several of you suggested that compound 2 might be formed from 1. CH3 OH O
Hour Examination #3, Chemistry 301X - December 15, 2005, 7:30-10:00pm
Chemiftry is the art of decompounding bodies, that is, of refolving compound bodies into their more fimple parts, and by combining thefe together, to reproduce the original compound wit
Answers to Hour Examination #1, Chemistry 302X-302A, 2005 1a
Cope Moves a double bond out of conjugation - not favorable. In addition, one double bond is less substituted, and hence, less stable. X O O Diels-Alder O Y O O O Moves double bond i nto the thr
Mary Martinez Experimental Date: 10/13/2010 Report Date: 10/20/2010 Title of Experiment: Separation and Purification of the Components of An Analgesic Powder Partner Name: Hitasha Kalola Abstract: This experiment is a two-week process but in the first wee
S ome Answers to Hour Examination #1, Chemistry 302/302A, 2004 1. In this variation of the Diels-Alder reaction, both the diene and the dienophile are cyclic compounds. The first complication is to decide whether the reaction will pass over an endo or exo
Answers to Hour Examination #3, Chemistry 301-301A - 2004 1. (a) There are two possible regiochemistries, each of which can, in principle, give cis or trans products.
OR H Br2 CH3 OH 1 possible regiochemistries - no stereochemistry implied (yet) H H Br
Some Answers to Hour Examination #3, Chemistry 301X - 2006 1. There are variations on what follows but here is a reasonable path. To get 3, one simply backtracks and then follows the pathway outline in Problem 85.
C H3 OH OH 1 C H3 O CH3 O H H 2O H 3O + C
C hemistry 301-301A - Answers to Hour Examination #3
1a. Standard hydration with rearrangement, and right off the last hour exam as well. Protonation goes to give the secondary, not primary carbocation, and a hydride shift then generates the more stable t
C hemistry 301A-301X Final Examination: January 12, 2005 Why, for example, should a group of simple, stable compounds of carbon, oxygen, and nitrogen struggle for billions of years to organize themselves into a professor of chemistry? What is the motive?
H our Examination #1, Chemistry 302-302A, March 1, 2004, 7:30-10:00 Obscurity. is painful to the mind. David Hume thanks to Susan M. Neider, former orgostudent 1 (16 points). Write arrow formalisms and provide detailed structures for the two unknown produ
Answers to Hour Examination #2, Chemistry 302X-302A, 2005 1. (a) Aldol followed by reductions: 1. H3O+/H2O (aldol) 2. H2/Pd/C (reduce) 3. NH 2NH 2/HOCH2CH 2OH/heat (WolffKischner - you could also use the Clemmenson) or 1. LiAlH 4 2. H2O cyclohexanone 3. H
Hour Examination #3, Chemistry 302-302A, April 28, 2005 Chemiftry is the art of decompounding bodies. Thomas Southwell, M.D. London, 1764. 1 (20 points). Alcohols, R-OH, are generally converted into halides, R-X, on reaction with HX. Thus: HCl OH (a) Writ
Answers to Exam 3, Chemistry 0243 2008 1. a.
H H H (CH3)3C H H H H H H H H
CH3 CH3 Cl
2. (a) CH2N2 (diazomethane) and light (b) CF3COOOH (c) KMnO4 or (b) and either HO /H2O or H3O /H2O (d) Br2/H2O (e) 1. BH3 2. HOOH/HO
You must do this First Question. It should take no more than five minutes) 1. (a). Draw a perfect structure for tert-butylcyclohexane in its energy minimum form. Include the hydrogens attached to the six-membered ring.
(b) Draw a perfect mechanism
Some answers to the Chemistry 301-301A Final Examination, January 12, 2005 1.
H3 C O H OH2 H3O + H2O H3 C O + CH3
O+ H H2O
H H3 C H O CH3 O
OH2 H H3 C O+ CH3 H O H2O H H +
CH3 OH H CH3 O
H CH3 H O
IR: 1725, 28
Hour Examination #3, Chemistry 301-301A, December 8, 2004
"One had to cram all this stuff into one's mind for the examinations,whether one liked it or not. This coercion had such a deterring effect on me that, after I had passed the final examination, I f
Answers to Hour Examination #3, Chemistry 301X - 2005 1.
re al produ c ts 1 . H3 O /H2 O (a) 2. Na
c an' t d is pl ac e H O w ith a nuc leo ph i le
1. H3 O /H2 O (b) OH (c) 1. CF3 COOOH 2. K OH/ H2O M arkov ni k ov ad di ti on th ro ug h m ore s
Some Answers to the Final Examination, Chemistry 301X- 2006 1. (a) OH HO A HO H H OH B
OH E H (b) Isomer A is an enol and will isomerize to the ketone form: HO A enol (c) Problem 15.46
H F OH
(d) One Possibility - there are others. one dibrom
Chemistry 301X Final Examination: January 24, 2006 If you are obliged to neglect any thing, let it be your chemistry. It is the least useful and the least amusing to a country gentleman of all the ordinary branches of science. Thomas Jefferson
Final Examination, Chemistry 301X, January 24, 2007 This Final Examination is different in very few respects from the hour exams with which you are all too familiar. However, there is choice. DO ONLY EIGHT (8) QUESTIONS PLEASE do not do all the questions.
Some Answers to the 301X Final Examination, January 24, 2007 1. The two diastereomers are, of course, the cis and trans diols. CH3 OH OH cis 1 trans 1 CH3 OH OH
The simplest mechanism through which both diols would give 2 and 3, is an SN1-like process goi
Answers to Hour examination #1, Chemistry 301-301A, 2003 1. (a) yes (b) no - atoms moved (c) yes (d) no - valence violated (e) no - valence violated (f) yes (g) yes (h) no - atoms moved 2. CH 3 O C H O C C N(CH 3 )2 H O H CH 3 O C C C N(CH 3 )2 H
CH 3 O C
Some Answers to Hour Examination #2, Chemistry 301X - 2006 1a and b. Here are the drawings: The two diastereomers are shown at the top and the products at the bottom. In these SN2 reactions, the leaving group tosylate must be in the position as shown so t
C hemistry 301-301A - Hour Examination #2, November 17, 2003 There aint no answer. There aint going to be any answer. There never has been an answer. Thats the answer. Gertrude Stein
1 (20 points). Explain carefully why reaction (a) fails but (b) succeeds
Some answers to Hour Examination #2, Chemistry 301-301A, 2003
1. (a) Bromide is not a strong nucleophile, and would never displace the poor leaving group ethoxide. SN1 is impossible as a primary cation would have to be formed. (b) Here, protonation of the
H our Examination #2, Chemistry 301-301A, November 15, 2004 Then, when the work was done my mother and father would stand there in the middle of the big, bright room and say poems or sing. How strange it seemed to me that all these serious, hard-working p
Answers to Hour Examination #2, Chemistry 301-301A - 2004.
1a. In general, sodium hydride forms the alkoxide which then does an intramolecular S N2 to form the epoxide. OH NaH O O
The stereochemical details are critical, however, as the energy m
Hour Examination #2, Chemistry 302-302A - 2005
Walt Disneys Comics and Stories, 1942 In the following questions, be pithy (but be right). Pay attention to detail! Lets make some molecules for a start. In Problems 1 and 2, you may use any inorganic reagent
H our Examination #2, Chemistry 301X - 2005, November 21, 2005, 7:30-10:00 pm As you get older, you start to give yourself permission to make a mistake. Whether you make it or not, youve got to reach. Interesting things can develop through that process. K
CHEM-UA 225 Organic Chemistry I
Recitation Worksheet 1
1) Draw the Lewis dot structure for the following neutral molecules: H 2O, BF3, F2 and N2
2) Draw the Lewis dot structures for the following charged molecules : OH -, NH4+, CH3+, OH3+
3) Draw Lewi