chem312 exam1 spring03

Chem312 exam1 - Oremistry312 Dr K Bailey Exam 1 Spring 2003 Print your name KEY I hereby certify that the work on this exam is completely my own

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Unformatted text preview: Oremistry312 Dr. K. Bailey Exam 1 Spring 2003 Print your name KEY I hereby certify that the work on this exam is completely my own. Signature DO NOT BEGIN THIS EXAM UNTIL YOU ARE INSTRUCTED TO DO SO. 1. Relax, take a deep breath and try to think clearly. Read over all the instructions within this exam carefully. Show all work for credit. Partial credit may be given for correct work. Do not invent new chemistg: on this exam. If you haven’t seen it before, don’t write it down! There are 6 numbered pages to this exam (including this one). Make sure you have all the pages. There are no blank pages. Be sure to answer all questions carefully and completely. You must sign your name on this exam for it to be graded. .“P’ 9' :59!" Good luck! GRADING Points Available Points Earned Multiple Choice Chemistry 312 Dr. K. Bailey Exam 1 Spring 2003 Part One: (15 points) Identify the functional groups presented in boxes on the structure below. Use the corresponding letter from the table to make your identification (i.e. an alcohol would be letter C). When you am done‘ cimIg the letter gongsggnding to the parent grbgg chain, A. alkene D. ether G. aldehyde J. amide M. benzene B. aikyne E. amine H. ketone K. carboxyiic acid N. cycloheptene C. alcohol F. nitro l. ester L. phenyl O. cycloheptyne 3 2 .- ' “¢‘0. : I Functional group #1. __l_ é./e:: J : Functional group #2: __E__ x ‘t: Functional group #3: ___B___ Functional group #4: __A__ 4 '0 '0 a o I I --—1 ‘ I I I I I I I I I I ———--l Parent carbon chain: M u o - - - —\ ......... - - Numbers refer to the carbon atoms! Part Two: (12 points) Complete the table below based on the carbons indicated by numbers on the structure above. Number H bridization Geomet —— —n (ll—(ETC HZ’C Hé‘CHéflCi'fZ ’ H; ~ Hz-ClHZ /CO 0 Chemistry 312 V Dr. (K. Bailey Exam 1 Spring 2003 @ CH3(C H930 H2 Structure A Part Three: (18 points) Multiple Choice. Use Structures A and B to answer the following. There is only one answer possible per question. "7’ m 3. The correct condensed structural formula for Structure 8 (above) is: 8- C10H2002 GE? CH3(CH2)sCOOH c. CH3(CH2)3CH2(CH2)4(O)COH d. (- wn‘te correct answer if not given T L ’6” 4. The number of DBE (double bond equivalents) in Structure A (above) is: a 1 WE: Clop‘mozj C10“ lb 2 C \j‘ _‘ f it 3 ’ ‘6' '” 2m”! '0 «mm d. (- write correct answer if not given 22 \ ' 4/2 1 2 vbg. CioH M, Z For Structure A, the maximum number of triple bonds possible with its molecular formula: MOQMLM 1%! m: 41,1;— (, H £501 a. O _ \D \ b. 1 “WWW” anm'l 2 3 c. d. 6. The number of positional isomers possible for JUST THE CARBON SKELETON SHOWN in Structure B is between: a: mug/found ’3 a. 1 and 5 b. 6 and10 c. 11 and 15 d. more than 15 isomers are possible {7 L 23‘7. The name of the longest carbon chain in Structure B is: a. nonane [9. decane c. tenane d. undecane JV; 48. Structure A and Structure B are: g, E- a. structural isomers N IF," V03? C A 0 b. geometric isomers C‘Dfimoz ‘0 10 2’ c. stereoisomers @ not related, not isomers Chemistry 312 Dr. K, Bailey Exam 1 Spring 2003 Part Four: (20 points) Use the letters below to identify the following pairs of structures: Each answer can be used more than once! A. conformational isomers C. structural isomers E. unrelated B. geometric isomers D. identical (not isomers) CHa H3 , H H H H Simdwmt \SOCMK and H H H E 9 __c___ Ha H H H3 H H3 H3 Cbhfim’railmxo‘tfl and H C’E'lhf‘lc H H H H 10. A He 13. A use at M [l Problem 13 was thrown out! 4 points for everyonell Chemistry 312 Dr. K. Bailey Exam 1 Spring 2003 Part Five: (7 points) Use the carbon skeleton below to draw the following: 14. The LEAST stable form of 1 ,3—dimethyl-5-t-butylcyclohexane. 1 M3 to WNW}? {agglflin’mt t—hutyl locks chair so that it remains / equatorial! I \ (itj C *3; H (bun) mat) CH3 A both axial! H30 Part Six: (10 points) Identify each reaction as one of the three major reaction classifications (substitution, addition or elimination). If it is not one of the three write the word “OTHER” in the space provided. 6 4 .k C! ON 1,323; “piggy” L + NaCl 16. type of reaction: substitution OH ~ , W0" H2 W MN -———————-—-—->- 17. 0 Pd“: 0 . type of reaction: ___addition Extra Credit (3 points): Using the same rules as above, what kind of reaction is this? H + H /\[( H /\( ————.__._> type of reaction: other A tautomerization — note only H has moved! Chemistry 312 Dr. K. Bailey Exam 1 Spring 2003 3*?”"3‘9’ 73d” W” 51’ W93” "vr'i mix {iii (gr-r; Mn c. Part Seven: (18 points) Circle the name or structure that matches in each \" question. If a correct answer is not provided, draw the structure or write the iUPAC name in the space provided. N TE:ANYANSWERINA XW RA A P N E. '2' MO 33;]me H3 Ocmhfl 2-chloro-3-bromo-4,4-dimethyl-5- _ A propyiheptane 434 (U niflfifli Hg r E ' WWWle { Cfi 3-bromo-2-chloro-4-isohexane-4- 19. Cl 3' CH3 V ‘ 2,, methylpentene 3-hr0mo—Z-chloro—S—ethyl-4,4—dimcthyloctane 3.bmmo.2.ch|om.4,4.dimethy|.5. isooctane Write name here if not shown. ix “C t — — 6 )b‘, MWWM erigh MW 2 9M Q'womu CH3 Br 6-bromo-2,2-dimethoxyhept-4-yne CH3—-—€3—-~—CH2—-CE€—CH—CH3 I 2-bromo-6,6-dimethoxzhth-3-zne 20. We . ' 2-bromo-6,6-dimethoxyhept-1-yne V Write name here if not shown. 21 . 1-nitro-2—sec-butyicyclobut-1-ene N02 /‘%N02 QNW Draw structure here if not shown. ...
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This homework help was uploaded on 02/07/2008 for the course CHEM 312 taught by Professor Bailey during the Spring '03 term at Cal Poly.

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Chem312 exam1 - Oremistry312 Dr K Bailey Exam 1 Spring 2003 Print your name KEY I hereby certify that the work on this exam is completely my own

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