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Unformatted text preview: Return my exam in class Retum my exam in Clark 278 NAME Q Vasim g. HOUR EXAM ll 1. {14) Give the correct IUPAC name for each of the following compounds. Be sure to include the correct stereochemical designation using the EZ system for any atkene having stereochemistry. On the structure given, clearly indicate the priority assignments you used to determine any EZ designations you made. Use the letter “a." the word “Hi,” or the number “‘1 ." to designate the high priority group. The EZ designation mu give must be consistent with the priorities you assigned. A PERIODIC TABLE IS PROVIDED AT THE END OF THE TEST. You may separate the last page from the rest of the test. if you wish. to make it easier to use. CI I HchCH—CHZ C=CH CHs—CEC—CH CH 3! \ / _ 2 : a.(6} >C:C/ b. {8) CfiC C\CH’CH3 my?“ “25’ 0““ch 2 bus ' | CH3 CH3 a. l’hW-Z'U'MMW) Jul-llm- 3'1‘50Ml" Z» M19“- 5.7-.“ ”(3%)" 3' isoiwl’tl‘d'CZ- wwlynwl)ieplr°),(o- climv-L 7m 2. (8) Draw the structure of: '(E)—4-ethyl-2,3-dlmethyi-S-heptene. eff—0A a... / m 20H) -'- C CH) ‘OHMLwJ 3. (7) The reaction of 1-methyl-1-vinylcyclohexane with HCl in ether converts it to 1-chloro-1- isopropylcyclohexane as shown In the following equation. Write the steps in the mechanism for this process. Be sure to show the following: (1) the structure of any intermediates that are formed during the mechanism. (2}, what. if anything, is added or lost during each step of the mechanism. (3} any nonnzero formal charges found on the structures that you rite. REMEMBER: You may not use any materials except those that are iven in the e cation. it cl CH3 fl Cl ,CH3 °H=CH2 HC! CH 0L EH19! ‘CHs Hour Exam I! (a). Chemistry 301. Spring 2807. Page 1 of 7 pages 4. (7} When 2-methyi-2-butene is treated with bromine in water. the product that forms is the bromohydrin that is given below. Write the steps In the mechanism that shows how this reaction occurs. Be sure to show the following: (1) the structure of any intermediates that are formed during the mechanism. (2). what. if anything. is added or lost during each step of the mechanism. (3} an non-zero formal char as found on the structures that you write. REMEMBER: 1g; me not use an materials exce tthose that are iven in the uation. CH8\ ,CH3 Br: GH3\ _ xCHS /C=C.\ '_.0 CW“ 0 H H20 0145‘] \ 'er 3 OH H Hag at 0*: ,6": {ea/“*3 )Eé9\ ‘tho E j: EHBY L” ’ fly; 6 ' H ‘ Pr 5H at) H W BY B: ‘2’ 5424. 3 each) Below is given an array of reactions that begin with an aikene or an alkyne. or from a compound that can be made from one of these using a reaction we have studied this semester. On page 5 of the test is given a list of reagents we have leemed about. Each is designated with a letter and a number. In each box. write the letterinumber combination or combinations corresponding to the reagent or reagents required to carry out the indicated transformation. A sample has been filled in. YOU MAY SEPARATE THE TABLE FROM THE REST OF THE TEST TO MAKE IT EASIER TO USE. If there is more than one way to carry out the transformation. give oniy one. Some reagents may be used more than once. Others will not be used at all. In cases where two rea ents or sets of res ents are re uIred be sure to number them if u want to use them one after the other. If you do not number them. it means you want to add them simultaneously. Br H OH \C=C: éH-CHZOH O<H B, 0% CHchZOH n Crcn3 0“ ‘ 0% I-I\ ,H "ior 40H 0/ H CHzc H3 3 r\ f H O<CI O<H \H 0 Hour Exam ll {a}. Chemistry 301. Spring 2007. Page 2 of ? pages 6. (14) Geraniol is a naturally occurring pn‘mary alcohol that is produced by the scent glands of honeybees to help them mark nectar-producing flowers and locate their hives. Geraniol has molecular formula CmeO. a. (4) Calculate —SHOW YOUR WORKwthe degree of unsaturation represented by the formula C1uH130. Aw: lo—q—o+o+l =2 Hydrogenation of geraniol in ethanol using excess hydrogen in the presence of a Pro; catalyst led to absorption of two molar equivalents of H2 and converted It to a new compound having molecular formula CmHaO. H2 (excess). Pto; Ethanol “.22. [tus- ten—chase) Geraniol (C1OH150) C10H220 b. (2) Which gm of the following conclusions can be drawn from this hydrogenation experiment? CIRCLE ONE SENTENCE. 1} Geraniol contains two rings. 2} Geraniol contains no rings. 3) Geraniol contains one a: bond. 4) Geranio con 3 ns our double bonds. 5} Geraniol contains no multiple bonds. Ozonization of geraniol. followed by addition of hydrogen peroxide and acetic acid to the reaction mixture. led to formation of three products, A. B. and C, for which the structures are drawn in the following equation. 1. 03! CHZCI2 i‘ -7B°C 0 0 O O , 2. H20210H3002H II i! ll ll (3., + Geraniol (CmeO) H O’C‘CHz-CH; CH3 HO/chHz—OH + cH§CWCH3 A B C c. (1) NO CALCULATION IS REQUIRED. What is the degree of unsaturation in compound A? Degree of unsaturation = Z ( 2 Pi M5) {1. {7) Draw a structure for geraniol that is consistent with ALL of the information given in this problem. 0“; * (at) ((9de mm m3 \C'riLO-lzchzorlawzdt WW) Hour Exam li (a). Chemistry 301. Spring 2007. Page 3 of ? pages 7. {12, 3 each) If one is to prepare an organic compound using a known reaction. it is very important to be able to select the appropriate starting material. in each of the following equations, the starting material to be used has been replaced by a box. In each box. write the structure of a compound that would be expected to give the product shown as the maior product if it is treated with the reagents shown above andtor below the arrow under the conditions indicated. CH3 ,CHZCHS /C=C\ 4. H20 OH; H 09:3 1 H (0A) m o __ - 9 C2 2 0H b a’v- 0+2 2. NaBH4fH20 CH3\ I /CH-CH~CH3 CH3 CH3 v H at KOHIA / C. CH 3 —c- CH3 ethanol 0 1.BH3-THF ll 2. H202 at pH 8 buffer —-—-——I- O CHscHz/ “CH3 Hour Exam II {a}. Chemishy 301‘ Spring 2007. Page 4 of it pages 8‘ (14) Starting with methylenecyciohexane and acetylene as the only sources of carbon atoms for the final product, show how to synthesize (El-1,2-dichloro-3-cyolohexylpropene. You may use any other needed reagents or solvents so long as they do not oontn‘bute carbon atoms to the final product. About five steps are required. You may refer to the reagent table at the end of the test, but glease write our the formulas of the res eats rather than usin the letter/number combinations. UCHz methyfenecyclohexane 5 51 O—CQZ /CI AND About eps /C=C\ Cl H HCECH acetylene {EH .2—dichloro—3-cyclohexylpropene Plus any other needed reagents or solvents ah mm; I 20“ Cf 21.)“:02J0H' ) WEE???» O’mzw NH"! C2) ““9 WWW O/wILgCH . Hour Exam II (a). Chemisu-y 301. Spring 200?‘ Page 5 of 7 pages ...
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