MidtermSpring1998

MidtermSpring1998 - MW CHEM 2364/2463, Midterm Exam,...

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Unformatted text preview: MW CHEM 2364/2463, Midterm Exam, 3/2/98, Drs. Hogan, Naurnan & Weingarten "int your name ____ ___________ _______ "_______.___ _______ __ Mnt your TA's name__.________-fl______________ i. What is the proper disposal method for: a. A small volume of dichloromethane containing dissolved caffeine. b. fragments of a broken thermometer c. worn out lab cloth “nnmnwt d. 20 ml of 3N HN03 solution l l i i E i E e. a small volume of dichloromethane containing dissolved acetaminophen 2. Match these chemicals or reagents with the one hazard most likely to be associated with their laboratory use. ' ___sulfuric acid __Hethyl acetate a. carcinogenic ___bromine b. flammable __hydrazine (8% aqueous sol.) d. corrosive* __..ani|ine c. metabolic poison“ __‘chloroform e. explosive ___Tollens reagent ___methanol ___iodine ___hexane Y A metabolic poison acts by interfering with a vital biochemical function and is usually referred to in the laboratory as toxic. ** A corrosive poison acts by destroying tissue. CHEM 2364/2463. Midterm Exam, 3/2/98, Drs. Hogan, Nauman 8: Weingarten "int your name _______________ fi__ _________________ .._ M'int your TA's name_____.. ______ ___ ____ _________._.__.._ 3. Group the solvents chloroform, methylene chloride, carbon tetrachloride, hexane and ethyl acetate as: very polar intermediate non-polar HI‘NNLL l‘“-.\J‘Il?3" mammal-r 4. Think back to the experiment in which you prepared cyclohexene and as you review the procedure in your mind note ail the possible hazards. In other words. make a comprehensive list of those hazards and anything which you might reasonably expect to go wrong. WWWWFMMEWWEN l Ii"! Ni WWIVNREWW v z ‘ ‘ :‘WMf-‘lWWWMWWWWWW'WPWWWWHW CHEM 2364/2463, Midterm Exam. 3/2/98, Drs. Hogan, Nauman & Weingarten hit your name____ ____________ ___ _________________ __ Hint your TA's name________...___-_________c.___.__.___.. S. a. Estimate the percent composition of compound B in the vapor above a solution of 75%Aand 25% B. , a if s E‘; if; c; 5 b. Estimate the boiling point of the liquid at 75% A and 25% B. NOTE: Use a straight edge of some kind and make your estimates as accurate as you can. Temp. 100 75 50 25 0 £5 ‘iflmt-WK‘W .H'MWW ' . . 4 ‘ - “F :Wmm'mw R“rm”WWW“FEW?”WTW'flwrwwrhinfimw-mmiwmmwmeow-rmwwmwmware-man, CHEM 2364/2463, Midterm Exam, 3I2I98, Drs. Hogan, Naurnan & Weingarten 'H-r. Itm nwmvrliinwm‘mmmm- 7_ int your name __________ ____ ______________________ __ Hint your TA‘s name ____ _.__._,__ ____ ___ ____ ___..___ _____ _. 6. You are using TLC to follow the formation of cyclohexene from cyclohexanol. You have prepared four TLC platesl a standard and three plates from samples taken at various time intervals during the reaction. However. you have lost track of which spot on your standard is cyclohexene and which is cyclohexanol. l‘."‘ l5? F'l Nam-V .‘i'l.\".‘l‘ a. Use the three plates made at varioos time intervals during the reaction to relabel your standard. b. Describe some additional information which might be deduced from ‘ plates 2, and 3. solvent front start ' 2nd lst standard 3rd a: E. E a if: 3 7. You have just carried out a reaction which yields compounds A. B and C, for which you have known authentic samples. However, HPLC analysis of your product mixture has revealed four components. Describe briefly how y0u would identify which of the four components is the unknown compound. A. l W. Wfimt WWI www.myw w W - -'-“’ - A- 3" "W “w- ‘m«Winn-‘1WWWW“:7"L'WWWK"‘FTD‘WEWWWWW'WWWm-721Mm-rW-iar'lii‘ CHEM 2364/2463, Midterm Exam, 3/2/98, Drs. Hogan, Nauman & Weingarten "int your name_.___,,__________________._.________..____..._ Hint your TA's name____.._ ______ _____________________.c__ 8. Describe how you would separate five grams of a mixture of the following two compounds into its pure components: CH2000H CHgCHgOH N02 N02 CHEM 2364/2463, Midterm Exam, 3/2/98, Drs. Hogan, Nauman & Weingarten "rint your name_______ ____ ___________._____.____....._______ Vrint your TA's name___.______.___________.__.___.__.____.._ 9. a. What is the order of decreasing acidity of these acids? (strongest No. 1) CHz-H 0—H OOH COO-H CEO-H CI 80 O O A B C D E a. BDCEA b. DECBA C. EDBCA d. DBCEA e. DEBCA ‘i‘l‘i1"Mumffluwflifi-flHj;_1W1:"1i“flairI-“u; wry-r .;. “3 ‘. , ,.. . m ‘ A , T I j A H r F“ ' ' ‘ " c. ‘ - .m. 4.3 r .: i."v“'i"‘$uj.i\,\':i‘\ b. What is the order of decreasing basicity of these bases? (strongest No. 1) OW V“ GM '3’ H B C D E a. BAEDC b. ABDCE c. BACDE d. DBEAC e. BADCE NHC OCH 3 “Kmrmrmquyyfirm- :_i(v‘:‘. “i‘ir'ft‘rv‘q x; m w; 1 r...“ w ‘ rimmn‘mmmfimwmmmmgmwrmmm :Y'fi-‘KWMijW-I WWW i‘U-C CHEM 2364/2463, Midterm Exam, 3/2/98, Drs. Hogan, Nauman & Weingarten ‘int your name ____ __________________ _____ _.__.. _____ _.... *Hint your TA's name ____ ____________.________.___.._____.__ 10. a. Give the IUPAC name for the following structure: *3 9H C—CH— $Ha / CH3 Cl-h-(f—(E Br H b. Draw the structural formula (chair form) for cis—3-methylcyclohexanol CHEM 2364/2463, Midterm Exam, 3/2/98, Drs. Hogan, Naunjlan & Weingarten 'int your name_____.____._________c____._____._.._____.___ ‘H‘int your TA's name..._-_ ________ __.______ _______ ________. 11. Calculate the theoretical yield in grams and the percent actual yield of cyclohexene using the data below. Show your work! “’0 fl - O + A 87.5 mi 55.6 ml (density 0.963) (density 0.81 'l) 1 ; F i e: a E t; i E I . E E- _. :4 CHEM 2364/2463, Midterm Exam, 3/2198, Drs. Hogan, Naurrlan & Weingarten "int your name_ ________ _..._ _______ .____ ____ _._._______ Hint your TA's name_______________.______,___..____...___.._ 12. You have three samples to identify chemicaily. You know they are butanal, 2-butanone and 2,4-pentadione but you don't know which is which. Devise a simple chemical scheme to differentiate the three samples. (use no more than 2 qual. tests) CHEM 236412463, Midterm Exam, .3/2/98, Drs. Hogan. Naunfian 8: Weingarten na rne_..______,.____..__..._.________.____.___..___..-_ "int your ‘H-int your TA's name__..___________.__.____t ______ _._.______.__ 13. What qualitative anaiytical test(s) would give positive results with these molecules? If no test would be positive write "none". CH3 0 CH3 H0 0 Cl ;-'."n_n-'.mrv.wmm mumm-mwvs-vrgvmyfiv nmggg-nxr-qw w- CH3 0H CH3 10 l l l CHEM 2364/2463, Midterm Exam, 3/2/98. Drs. Hogan, Nauman 8: Weingarten in you name _________ ______.,.__ _________________ __ \rrint your TA‘s name ____ ____, ____ ________ _______ ____.___ 14. a. Draw a detailed mechanism of an 5N1 reaction between (R)-3-chloro-3- methylhexane and methanol. List the important features influencing SNl reactions. CH3CHL\\ .NwC-—O CH3” CHZCHZCHZ b. Draw a detailed mechanism of an SNZ reaction between (R)-2-chlorobutane and hydroxide ion. List the important features influencing 8N2 reactions. CH§\ H‘..\\\C —0 CH3CH2 'll Fill . CHEM 2364/2463, Midterm Exam, 3/2/98, Drs. Hogan, Naurnan & Weingarten "int your name_.__________.________.._________..._...___._____ wint your TA's name_____.____._________._____.___..._____.____ 15. A chiral alcohol A, C7H14O, on heating with concentrated phosphoric acid yielded, according to HPLC analysis, a mixture of two components. The two components were shown by Mass spec. analysis to be isomers B and C, C7H12. Compounds B and C were both chiral and each gave a positive test with Bra in carbon tetrachloride. Further dehydrogenation of B or C yielded toluene. Draw plausible structures for A, B and C. ‘12 CHEM 2364/2463, Midterm Exam, 3/2/98, Drs. Hogan, Naurnan & Weingarten "int your name _______________ ___ _________________ __ Mint your TA's name_______________ ____ __._ _____ __._...__ 16. Propose a two step synthesis for compound B starting with compound A and any commercially available reagents. 0 ,CH2, ,CH ,0H __ __ “" HO CH2 aCHZ >- > '1“ A O B 13 Humor-m: ’lifi‘q-IJTI5u ‘sz‘- H I Am .A .r a l u ‘ A u .. l "x. l. . , - - i - . a i - . i u .‘ i"'liil\1"h“"‘L:‘IH‘:lmfl‘tfil‘lfl wru. vmv-vmmw-i.‘ mowmmwrmn 'ii‘i'i.“'r""- “ mmwn c. f. , E "r g; E F .- E. P 8-5.”! 17. “'int your name___.___________..____._____._____-__.____.._..__ int your TA's name___,__ ____ __._.___.___________._..___.__ BONUS PROBLEM FOR 2364/REQUIRED FOR 2463 You have 129 of compound A in 100ml of water and you wish to extract it into methylene chloride. Would you be able to extract more compound A with a single extraction Using 100ml of methylene chloride or two extractions each using 50ml of methylene chloride? SHOW YOUR CALCULATION! Assume the distribution coefficient is: K = 9.0 = [ADCM1/[AH0H] CHEM 2364/2463, Midterm Exam, 3/2/98. Drs. Hogan, Nauman 8: Weingarten 14 ...
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This note was uploaded on 09/22/2008 for the course CHEM 2364 taught by Professor Davila during the Summer '08 term at LSU.

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MidtermSpring1998 - MW CHEM 2364/2463, Midterm Exam,...

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