Name: Question 1-10 are 20 points each.

St. Johns University Department of Chemistry CHE 2241LDate: !r"ani# La$ %ina& E'am

Molar mass of Benzaldehyde 106.12, acetone 58.08. n the column chromato!raphy e"periment a student accidently used acetone as the first mo#ile phase and petroleum ether as the second mo#ile phase predict in $hich #ea%er the fluorene and fluorenone $ill #e in. a& #ea%er '1 fluorene and #ea%er '2flourenone #& #ea%er '1 fluorenone and #ea%er '2flourene c& #ea%er '1 fluorene and fluorenone #ea%er '2 nothin! 1& n the column chromato!raphy e"periment a student used petroleum ether as the first mo#ile phase and acetone as the second mo#ile phase predict in $hich #ea%er the fluorene and fluorenone $ill #e in. a& #ea%er '1 fluorene and #ea%er '2flourenone #& #ea%er '1 fluorenone and #ea%er '2flourene c& #ea%er '1 fluorene and fluorenone in #ea%er '2 nothin! 1& n the column chromato!raphy e"periment $here $ould you e"pect the find fluorene and fluorenone( a& fluorenone in #ea%er '1 and fluorene in #ea%er '2 #& fluorene and fluorenone in #ea%er '1. c& fluorene in #ea%er '1 and fluorenone in #ea%er '2 #ecause fluorene is polar and fluorenone is nonpolar fluorene is nonpolar and fluorenone is polar fluorene and fluorenone are #oth polar. )hich of these statements are true( t is impossi#le to separate t$o *ery similar compounds #y column chromato!raphy such as fluorene and fluorenone. +luorene can #e separated from fluorenone #y column chromato!raphy usin! acetone as the sol*ent ,he order of elution from an alumina column usin! petroleum ether and acetone is polar flourenone and then nonpolar fluorene.

+luorene $hich is nonpolar is easily eluted from alumina column #y petroleum ether and then the more polar fluorenone is eluted #y acetone. -afety. Based on your e"perience $hich of the follo$in! chemicals are flamma#le. a& petroleum ether #& acetone d& methanol d& $ater e& /ll of the a#o*e e"cept d. 2& -afety. Based on your e"perience $hich of the follo$in! chemicals are flamma#le. a& diethyl ether #& acetone d& methanol d& #enzyl alcohol e& /ll of the a#o*e e"cept d. 2&-afety. 0sin! a Bunsen #urner to heat and distill a product is less dan!erous if the compound isn1t flamma#le . )hich compound $ould you heat and distill $ith flame. a& petroleum ether #& acetone d& methanol d& #enzyl alcohol e& diethyl ether f& ethanol. 2&,he reason $e used a flas% heater to distill ethyl ether from methyl #enzoate rather than a Bunsen #urner is #ecause a& ethyl ether has a hi!h #oilin! point #& ethyl ether is flamma#le c& ethyl ether is carcino!enic d& ethyl ether is anesthetic. 2 & n the preparation of 3-42,6-5imethylphenyl&chloroacetamide in the 6idocaine e"periment $hy $as it important to use dry e7uipment( 2 & n the preparation of methyl #enzoate e"periment $hy $as it important to use dry e7uipment(

2& Based on your e"perience in the 8annizzaro reaction, ho$ you $ould separate he"anoic acid from he"anol( 42 points for each #lan%& /dd 9999999999999 to solu#ilize the he"anoic acid and e"tract the he"anol $ith 999999999999999, separate layers in a separatory funnel and neutralize the a7ueous layer $ith 99999999999. ,he a7ueous layer should contain the he"anoic acid $hich can #e 99999999$ith a 99999999999and the diethyl ether should contain the he"anol $hich can #e separated #y 99999999999. :& ;o$ $ould you isolate #enzoic acid, if you had the #enzoic acid as the sodium salt in the a7ueous layer( $ould neutralize $ith 6M ;8l. $ould neutralize $ith 6M 3a<;. $ould add $ater . $ould neutralize $ith a com#ination of 6M ;3<2 and 6M ;2-<: . :& ;o$ $ould you isolate Benzyl alcohol, if you had the #enzyl alcohol in diethyl ether( $ould e"tract $ith 6M ;8l, separate distill the a7ueous layer. $ould $ould distill the diethyl ether, the #enzyl alcohol should #e in the recei*er. $ould $ould distill the diethyl ether, the #enzyl alcohol should #e in the distillation flas%. :& Based on your e"perience in the 8annizzaro reaction, ho$ you $ould separate #enzoic acid from #enzyl alcohol( 42 points for each #lan%& /dd 9999999999999 to solu#ilize the #enzoic acid and e"tract the #enzyl alcohol $ith 999999999999999, separate layers in a separatory funnel and neutralize the a7ueous layer $ith 99999999999. ,he a7ueous layer should contain the #enzoic acid $hich can #e 99999999$ith a 99999999999and the diethyl ether should contain the #enzyl alcohol $hich can #e separated #y 99999999999. n the Benzenone o"ime a student failed to !et a solid after transferrin! the cooled reaction into a #ea%er. ,he student loo%ed #ac% and found that he or she had added :0 ml of ethanol and 25 m6 of 20 = sulfuric acid to the 100 m6 >B+. ?"plain the stran!e results( n the Benzenone o"ime e"periment ,he student loo%ed #ac% and found that he or she had added 25 m6 of 20 = sodium hydro"ide. ?"plain $hy it $as necessary to add the rea!ent( 5& n the Benzenone o"ime e"periment, durin! the $or% up 20 = sulfuric acid is added ?"plain $hy it $as necessary to add the rea!ent( ;int, if you don1t add the acid you cannot isolate the o"ime, consider the mechanism.
2

,68. 5etermine the >f *alues of the t$o un%no$ns.

n the esterification of methyl #enzoate su!!est t$o $ays that can #e used to dri*e the reaction to completion( @& n the esterification of methyl #enzoate e"periment if you use one mole of #enzoic acid $ill you !et the #est results( a&Aes you $ill #& 3o you $ill not ?"plain ( )hy(

8& n the di#enzalacetone e"periment determine the limitin! rea!ent, the theoretical yield and the percent yield. -tartin! $ith 2@.50 ! #enzaldehyde, and @.26 ! acetone and yieldin! 1:.6: ! of product. 0se si!nificant fi!ures.

B& dentify one of the products you made this semester. ,he chemical formula for the product is 8@;8<. Based on the 3M> and > sho$n #elo$ also, identify the %ey pea% in the > and 2 pea%s in the 3M>.

10& )hy do you add ethanol to purify di#enzalacetone( 3ame the process.