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CHE276 Organic Chemistry laboratory I Quiz Fall 2013 ast !ame" First !ame" #tu$ent I%" 1& ' sam(le )or thin layer chromatogra(hy containing t*o com(oun$s +say, t*o $ye molecules- *as contaminate$ by a stu$ent *ith t*o other com(oun$s& .he ne/t stu$ent came an$ run the . C o) the contaminate$ sam(le& 0oul$ the secon$ stu$ent still be able to get the correct 1) 2alues )or the original t*o com(oun$s3 '& 4es 5& !O C& Cannot be $etermine$& 4E#& .he 1) 2alue ne2er change *hen there is no co2alent reactions& 2& 6sing a (olar sol2ent, a stu$ent runs a . C )or t*o molecules on the same . C (late, *hich molecule *ill ha2e a smaller 1) 2alue3 '& .he more (olar molecule& 5& .he less (olar molecule& C& Cannot be $etermine$ *ith the in)ormation gi2en& .he more (olar molecule al*ays has a smaller 1) 2alue than the non(olar molecule, regar$less o) the (olarity o) eluent sol2ent& .his is because (olar molecules interact *ith silica gel stronger than non(olar molecules $o& 3& 6sing a non(olar sol2ent, a stu$ent runs a . C )or t*o molecules on the same . C (late, *hich molecule *ill ha2e a smaller 1) 2alue3 '& .he more (olar molecule& 5& .he less (olar molecule& C& Cannot be $etermine$ *ith the in)ormation gi2en& .he more (olar molecule al*ays has a smaller 1) 2alue than the non(olar molecule, regar$less o) the (olarity o) eluent sol2ent& 7& Consi$ering tem(erature an$ solubility, *hat *oul$ be the criteria )or a goo$ sol2ent )or recrystallization o) a targete$ molecule3 '& 8olar sol2ent is goo$, non9(olar sol2ent is not e))ecti2e& 5& It $e(en$s on the )unctional grou( o) the targete$ molecule& C& It $issol2es the targete$ molecule at high tem(erature, but not at lo* tem(erature& %& It $issol2es the targete$ molecule slo*ly& 'ns*er is C

:& .he . C o) a com(oun$ is run t*ice on t*o $i))erent . C (lates, once in a (olar sol2ent, the other in a non9(olar sol2ent& In *hich eluent sol2ent *ill the s(ot ha2e a high 1) 2alue3 '& !on(olar sol2ent& 5& 8olar sol2ent& C& Cannot be $etermine$ *ith the in)ormation gi2en& .he (olar sol2ent interacts *ith the com(oun$ on . C stronger than the non(olar sol2ent $oes& #o, the com(oun$ *ill be mo2e$ u( more by (olar sol2ent than by non(olar sol2ents& .hus, the (olar sol2ent *ill cause the s(ot to ha2e a higher 1) 2alue& 6& 0hat ;in$ o) a<ueous solution shoul$ be a$$e$ to the organic solution containing the )ollo*ing t*o organic molecules in or$er to se(arate them by e/traction3

'& 'n aci$ic solution& 5& ' basic solution& C& ' solution *ith high concentration o) salts& %& .here is no goo$ *ay to se(arate the t*o molecules base$ on e/traction metho$& .he basic solution *ill causes a reaction 1COOH +org- = 59 1COO9 +a<- = 5H, an$ bring the aci$ into a<ueous solution in a negati2ely charge$ )orm& 7& 'n a<ueous solution contains, 8hCOO9!a=, ho* shoul$ a stu$ent reco2er the molecule in the (ure )orm o) 8hCOOH3 '& '$$ an aci$ic a<ueous solution an$ an organic sol2ent, $o the e/traction an$ remo2e the organic sol2ent& 5& '$$ an aci$ic a<ueous solution an$ an organic sol2ent, $o the e/traction an$ remo2e the a<ueous sol2ent& C& '$$ a basic a<ueous solution an$ an organic sol2ent, $o the e/traction an$ remo2e the organic sol2ent& %& '$$ a basic a<ueous solution an$ an organic sol2ent, $o the e/traction an$ remo2e the a<ueous sol2ent& E& >ust remo2e the a<ueous sol2ent& 5y a$$ing the aci$ic a<ueous solution, 8hCOO9 = H= 8hCOOH +org-, an$ then se(arate the organic an$ a<ueous (hases& .he organic (hase contain only 8hCOOH, an$ then remo2e the organic sol2ent by rota2a(, (ure 8hCOOH is obtaine$& 1emo2ing the a<ueous (hase *ill gi2e !aCl salt&

?& 0hat ;in$ o) a<ueous solution shoul$ be a$$e$ to the organic solution containing the )ollo*ing t*o organic molecules in or$er to se(arate them by e/traction3

'& 'n aci$ic solution& 5& ' basic solution& C& ' solution *ith high concentration o) salts& %& .here is no goo$ *ay to se(arate the t*o molecules base$ on e/traction metho$& 'n aci$ic solution *ill cause a reaction 1!H2 +org- = H= 1!H3= +a<-, an$ bring the amine into a<ueous solution in the ammonium, charge$ )orm& @& 'n a<ueous solution containing an amine9base$ salt +ammonium-, ho* shoul$ a stu$ent reco2er the amine in (ure )orm by e/traction3 '& '$$ an aci$ic a<ueous solution an$ an organic sol2ent, $o the e/traction an$ remo2e the organic sol2ent& 5& '$$ an aci$ic a<ueous solution an$ an organic sol2ent, $o the e/traction an$ remo2e the a<ueous sol2ent& C& '$$ a basic a<ueous solution an$ an organic sol2ent, $o the e/traction an$ remo2e the organic sol2ent& %& '$$ a basic a<ueous solution an$ an organic sol2ent, $o the e/traction an$ remo2e the a<ueous sol2ent& E& >ust remo2e the a<ueous sol2ent& 5y a$$ing a basic a<ueous solution, 1!H3= +a<- = OH9 1!H2 +org- = H2O, an$ then se(arate the organic an$ a<ueous (hases& .he organic (hase contains only 1!H2, an$ then remo2es the organic sol2ent by rota2a(, (ure 1!H2 is obtaine$& 1emo2ing the a<ueous (hase *ill gi2e !aCl salt& 10& 0hat ;in$ o) a<ueous solution shoul$ be a$$e$ to the organic solution containing the )ollo*ing t*o organic molecules in or$er to se(arate them by e/traction3

'& 'n aci$ic solution& 5& ' basic solution& C& ' solution *ith high concentration o) salts& %& .here is no goo$ *ay to se(arate the t*o molecules base$ on e/traction metho$& !either molecule is aci$ic nor basic, so there is no goo$ *ay to se(arate by e/traction& 11& 0hat metho$+s- *oul$ you (ro(ose to attem(t to se(arate the )ollo*ing t*o molecules3

'& E/traction an$ 1ecrystallization 5& E/traction an$ Column chromatogra(hy C& 1ecrystallization an$ Column chromatogra(hy %& Only recrystallization E& Only Column chromatogra(hy column )or sure, recrystallization nee$ s;ill an$ e/(erience, but most li;ely *ill *or; 12& 0hen a mi/ture o) )our com(oun$s is elute$ through a column, Com(oun$ A comes out the )irst, then Com(oun$ 4, B, an$ 0& 0hat is ran;ing o) the )our com(oun$s )rom high to lo* (olarity3 '& A,4,B,0 5& 0, B, 4, A C& 0,A,4,B %& Cannot be $etermine$ base$ on the in)ormation& Colecule comes out later, mo2e slo*er on column, has the higher (olarity than molecule comes out )irst& 13 0hen a mi/ture o) t*o com(oun$s are elute$ through a column to be se(arate$, but the com(oun$s ne2er come out a)ter a long time& 0hat may li;ely be the solution to this (roblem3
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'& >ust ;ee( running the column *ith more eluent sol2ent& 5& 1un the column all o2er again using ne* sam(le, an$ *ith more (olar eluent sol2ent& C& 1un the column all o2er again using ne* sam(le, an$ *ith less (olar eluent sol2ent& %& Cannot be $etermine$ base$ on the in)ormation& >ust li;e . C, *hen the sol2ent is not (olar enough, the molecules on the column or tlc $o not enough& 17& 0hen a mi/ture o) t*o com(oun$s is elute$ through a column to be se(arate$, both com(oun$s come out rather <uic;ly as a mi/ture *ithout any se(aration& 0hat may li;ely be the solution to this (roblem3 '& %o not a((ly (ressure, an$ let the sol2ent come out 2ery slo*ly& 5& 1erun the column *ith more (olar eluent sol2ent& C& 1erun the column *ith less (olar eluent sol2ent& %& Cannot be $etermine$ base$ on the in)ormation& 0hen the sol2ent is too (olar, the molecules *ill mo2e )ast *ithout se(aration& 1:& Com(are a crystal that is (ure o) one com(onent an$ a crystal that is im(ure, ho* *oul$ their melting (oints be $i))erent3 '& the im(ure crystal has higher melting (oint an$ narro*er melting range& 5& the im(ure crystal has lo*er melting (oint an$ broa$er melting range& C& the im(ure crystal has lo*er melting (oint an$ narro*er melting range& 5 16& 0hat (ro(erties o) molecules are im(ortant )or it to )orm crystals3 '& the sha(e o) the molecule& 5& the symmetry o) the molecule& C& ho* )le/ible the molecule is& %& all o) the abo2e& % 17& I) the boiling (oints o) t*o com(oun$s are se(arate$ by more than DAE $egree celsius, then sim(le $istillation *ill be su))icient& 0hat is DAE3 '& 10 $egree C 5& 3: $egree C C& 70 $egree C %& 10: $egree C C 1?& I) the atmos(here (ressure in contact *ith a li<ui$ is re$uce$, *hat *oul$ ha((en to the boiling (oint o) that li<ui$ 3 '& increase, 5& remain the same,
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C& $ecrease C 1@& 0hich o) the )ollo*ing t*o mi/tures can be more easily se(arate$ by $istillation3 . is the boiling tem(erature o) the sam(le& '

'& .he one on the le)t& 5& .he one on the right& C& Cannot be $etermine$ by the in)ormation gi2en& C 20& 0hat is the name o) the ty(ical sel)9assembly )orme$ by CH3+CH2-11O#O39!a= in an a<ueous solution3 '& Coin stac; assembly 5& Cicelle C& Fesicles %& #ur)actant E& i(i$ 5 21& 0hat is the name o) the ty(ical sel)9assembly )orme$ by the )ollo*ing molecule in an a<ueous solution3

'& Coin stac; assembly 5& Cicelle C& Fesicles

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%& #ur)actant E& i(i$ C 'lso, 2esicle are ma$e o) li(i$ bilayers& 22& 0hich o) the )ollo*ing t*o molecules is less (olar3

'& .he one on the le)t& 5& .he one on the right& C& Cannot be $etermine$ base$ on the in)ormation gi2en& Hy$rogen bon$ $onor has higher (olarity than hy$rogen bon$ acce(tor& Hy$rogen bon$ $onor is al*ays also hy$rogen bon$ acce(tor& Hy$rogen bon$ $onor causes the molecule )orm hy$rogen bon$ing *ith itsel)& Hy$rogen bon$ acce(tor only )orm hy$rogen bon$ing *ith other molecules than has hy$rogen bon$ $onor& 23& 1uning 1,29(entane$iol an$ 19(entanol on the same . C (late, *hich *ill ha2e a higher 1) 2alue on the . C (late3 '& 19(entanol 5& 1,29(entane$iol C& cannot be $etermine$ higher 1) 2alue im(lies lo* (olarity, less hy$rogen bon$ing $ecreases (olarity& Consi$er the )ollo*ing 3 $rug molecules&

27& 0hich molecule is an organic base3 '& molecule on the le)t& 5& molecule in the mi$$le C& molecule on the right %& all o) them E& molecules in the mi$$le an$ on the right Organic base has nitrogen atom that has lone (air o) electron that are not conGugate$&
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1!H2, 12!H are bases& .he )ollo*ing molecules are note bases& the electron on the nitrogen is not a2ailable )or (rotons because o) the strong conGugation *ith the carbonyl grou(&

2:& 0hich molecule is a conGugate base o) an organic aci$3 '& molecule on the le)t& 5& molecule in the mi$$le C& molecule on the right %& molecules on the le)t an$ in the mi$$le E& molecules in the mi$$le an$ on the right 1COO9 26& 0hich molecule is neither an organic aci$ nor organic base3 '& molecule on the le)t& 5& molecule in the mi$$le C& molecule on the right %& molecules on the le)t an$ in the mi$$le E& molecules in the mi$$le an$ on the right