,transcrib]'s ,notes3 ,typographical & punctuation errors h be5 sil5tly correct$4 ,a ,fur!r ,inve/igation ( ! ,symmetrical ,*loride ( ,p>anitroor?osulphob5zoic ,acid4 ,diss]tation4 ,submitt$ to ! ,bo>d ( ,univ]sity ,/udies ( ! ,johns ,hopk9s ,univ]sity = ! ,degree ( ,doctor ( ,philosophy4 -- by -- ,william ,e4 ,h5d]son4 #ahig ,ackn[l$gm5t4 ,! au?or e/eems x a privilege z well z a pleasure to give expression to 8 s9c]e s5se ( gratitude to ,pr(4 ,rems51"u ^: guidance ?is "w 0 c>ri$ on n only = in/ruction receiv$ 9 ! lecture room1 b = 8 frequ5t sugge/ion1 & 8 con/ant & fri5dly int]e/ 9 ! "w z x progress$4 ,^! h at all times be5 an enc\ragem5t & an inc5tive4 ,he wi%es also to express 8 appreciation ( ! in/ruction & k9dly guidance 9 ! laboratory1 ( ,drs4 ,morse & ,r5\f1 z well z ( ,dr4 ,ames ( ! ,physical ,laboratory4 ,cont5ts4 ,i4 ,introduction4 ,page #a ,,ii4 ,prep>ation ( ! ,acid ,potassium ,salt ( ,p>anitroor?osulphob5zoic ,acid4 #f ,,iii4 ,prep>ation ( ! ,symmetrical ,*loride ( ,p>anitroor?osulphob5zoic ,acid4 #ab ,,iv4 ,prop]ties ( ! ,symmetrical ,*loride ( ,p>anitroor?osulphob5zoic ,acid4 #ai ,v4 ,! ,action ( ,b5z5e & ,alum9ium ,*loride on ! ,symmetrical ,*loride ( ,p>anitroor?osulphob5zoic ,acid4 #bb ,! ,b>ium ,salts ( ,p>anitroor?ob5zoybb5z5esulphonic ,acid4 #bd ,,vi4 ,! ,action ( ,alcohols on ! ,symmetrical ,*loride ( ,p>anitroor?osulphob5zoic ,acid4 #cj #a4 ,me?yl ,alcohol4 #ca #b4 ,e?yl ,alcohol4 #cb ,action ( ,e?yl ,alcohol on ! ,unsymmetrical ,*loride4 #cf ,,vii4 ,! ,action ( ,ph5ols on ! ,symmetrical ,*loride ( ,p>anitroor?osulphob5zoic ,acid4 #ch #a4 ,ph5ol4 #dj #b4 ,or?ocresol4 #dh #c4 ,p>acresol4 #ea #d4 ,hydroqu9one4 #ec #e4 ,resorc94 #ef #f4 ,pyrogallol4 #ei #g4 -naph?ol4 #fa ,,viii4 ,! ,action ( ,anil9e on ! ,symmetrical ,*loride ( ,p>anitroor?osulphob5zoic ,acid4 #fb ,,ix4 ,! ,action ( ,phosphorus ,oxy*loride on ! ,fusible ,anilid ( ,p>anitroor?osulphob5zoic ,acid4 #ga ,x4 ,! ,action ( ,reag5ts on ! ,dianil ( ,p>anitroor?osulphob5zoic ,acid4 #gg #a4 ,( ,hydro*loric ,acid4 #gg #b4 ,( ,alcoholic ,pota%4 #gh #c4 ,( ,glacial ,acetic ,acid4 #gi ,,xi4 ,conclusions4 #hb ,biographical4 #he ,i4 ,introduction4 ,! sulphob5zoic acids h be5 ! subject ( inve/igation 9 ?is laboratory = a numb] ( ye>s pa/4 ,among ! _m int]e/+ facts t h be5 br\ght to light 9 ! c\rse ( ?is /udy1 p]haps no o!rs h be5 att5d$ ) m int]e/ ?an ! discov]y ( well *>act]iz$ isom]ism 9 ! case ( ! *lorides ( or?osulphob5zoic acid1 & its p>anitro d]ivative2 toge!r ) ! prep>ation ( a s]ies ( isom]ic d]ivatives ( ^! sub/ances4 ,! *lorides !mselves h be5 isolat$ 9 ! cry/all9e condition1 & h be5 f\nd to diff] m>k$ly1 n only 9 *emical1 b 9 physical prop]ties z well4 ,! fir/ evid5ce t su* isom]ism exi/$1 0 obta9$ by ,rems5 & ,coates#a :o1 9 ! c\rse ( an inve/igation ( ! action ( anil9e ^u ! *loride ( or?osulphob5zoic acid1 obta9$ two isom]ic anilids q diff]5t 9 prop]ties1 :i* !y designat$ z fusible & infusible respectively4 ,! foll[+ ye>1 ,rems5 & ,kohl]#b obta9$ "o ( ! *lorides 9 cry/all9e =m1 toge!r ) an oil :i* !y did n succe$ 9 cry/alliz+4 ,?is h[ev] 0 accompli%$ ! succe$+ ye> by ,rems5 & ,saund]s#c1 & a /ill m satisfactory result 0 obta9$ by ,rems5 & ,mc,kee#d 9 #ahie4 ,! *loride melt+ at #gi 0 f\nd to yield only ! fusible anilid1 toge!r ) an anil1 :ile f ! l[] melt+ *loride1 9 addition to ^!1 ! infusible anilid 0 also =m$4 #a ,am4 ,*em4 ,j\rn4 ,,xvii1 #caa4 #b ,ibid ,,xvii1 #bcj4 #c ,ibid ,,xvii1 #ced4 #d ,ibid ,,xviii1 #gid4 ,9 #ahie1 ,gray#e isolat$ ! two correspond+ isom]ic *lorides ( p>anitroor?osulphob5zoic acid1 ! l[] melt+ *loride be+ obta9$ 9 small quantity only4 ,! succe$+ ye> ,hollis#f made a m c>eful /udy ( ?is l[] melt+ *loride1 & prep>$ x 9 consid]able quantity4 ,f evid5ce drawn f ! action ( ammonia ^u ^! *lorides1 tak5 9 connection ) a numb] ( o!r facts1 ! high] melt+ *loride is id5tifi$ z ! "o possess+ a symmetrical /ructure1 :ile ! l[] melt+ *loride possesses an unsymmetrical /ructure4 ,! fir/ "o1 :5 treat$ ) ammonia is sl[ly trans=m$ into ! ammonium salt ( p>anitrob5zoic sulph9ide3 #e ,inaug4 ,diss4 ,j4 ,h4 ,univ4 #ahie4 #f ,inaug4 ,diss4 ,j4 ,h4 ,univ4 #ahif4 ,,co _/ ,c,o,cl _/ ,n4,,nh _/ _/ _/ ,c,h----,,s,cl #d,,nh ,c,h----,,s #b,,nh,cl4 ,,no ,,no :ile ! l[] melt+ *loride is quickly trans=m$ into ! ammonium salt ( p>anitroor?ocyanb5z5esulphonic acid3 ,c,cl _/ _/ ,o ,,cn _/ _/ _/ ,c,h----,,s #d,,nh ,c,h----,,s,,onh #b,,nh,cl4 ,,no ,,no ,gray's /udy ( ! symmetrical *loride 0 conf9$ = ! mo/ "p to ! prep>ation ( a s]ies ( salts ( ?is latt] acid1 & to an inve/igation ( ! action ( anil9e ^u ! *loride itself4 ,x 0 ?\ght to be ( int]e/ to ext5d ?is /udy to a wid] range ( reactions1 z well z to improve1 if possible1 ! me?od ( prep>+ ! *loride 9 pure condition4 ,at ! sugge/ion ( ,pr(4 ,rems5 ?is "w 0 accord+ly und]tak54 ,,ii4 ,prep>ation ( ,mat]ial4 ,! me?od employ$ 9 ! prep>ation ( p>anitroor?osulphob5zoic acid 0 ess5tially t describ$ by ,h>t1#g ,ka/le1#h ,gray#i & ,hollis4#aj ,! details ( x are repeat$ "h = ! purpose ( call+ att5tion to c]ta9 facts t came "u ! au?or's notice4 #g ,am4 ,*em4 ,j\rn4 ,i1 #cej4 #h ,ibid ,,xi1 #agg4 #i ,inaug4 ,diss4 ,j4 ,h4 ,univ4 #ahde4 #aj ,inaug4 ,diss4 ,j4 ,h4 ,univ4 #ahif4 #ajj grams ( p>anitrotolu5e are add$ to #djj grams ( fum+ sulfuric acid1 & ! mixture heat$ 9 a balloon flask at #ajj on a wat] ba?4 ,! heat+ is cont9u$ until a few drops ( ! mixture1 add$ to cold wat]1 dissolves completely to a cle> solution4 ,! "t requir$ = ?is op]ation v>ies mu* ) ! conditions4 ,cont9u$ /irr+ v consid]ably ha/5s ! reaction1 z p>anitrotolu5e =ms a lay] on ! acid1 :i* pres5ts a small surface to its action4 ,) con/ant /irr+ ! reaction is complete 9 a few h\rs1 :]eas if no /irr+ is resort$ to1 z mu* z sev]al days may be requir$1 especially :5 l>ge quantities are employ$ at "o "t4 ,:5 ! reaction is complete1 ! mixture is p\r$ into a l>ge volume ( wat]1 & neutraliz$ ) calcium c>bonate4 ,9 ! filtrate f calcium sulphate1 ! calcium salt ( p>anitroor?otolu5e sulphonic acid is f\nd1 & ?is is conv]t$ into ! potassium salt 9 ! usual way4 ,! oxidation ( ! potassium salt is effect$ z foll[s4 #ej grams ( ! salt are dissolv$ 9 #b litres ( wat]1 & to ?is is add$ a solution ( #ae grams ( potassium hydroxide4 ,! mixture is heat$ to #ajj on a wat]-ba?1 & :5 ?is temp]ature is rea*$1 #aaj grams ( potassium p]manganate are add$4 ,heat+ is cont9u$ until ! solution is decoloriz$1 c>e be+ tak5 to prev5t ! evolution ( free oxyg54 ,! oxides ( manganese are !n filt]$ (f1 ! filtrate neutraliz$ ) hydro*loric acid1 & evaporat$ to ab\t "o fif? ( its orig9al volume4 ,/rong hydro*loric acid is !m add$ 9 excess1 & on cool+ ! acid potassium salt ( p>anitroor?osulphob5zoic acid sep>ates 9 v sl5d] colorless ne$les completely fill+ ! liquid4 ,= ! success ( ?is op]ation x is important t ! potassium salt ( p>anitroor?otolu5esulphonic acid & ! potassium hydroxide %\ld bo? be p]fectly dissolv$ be=e !y are heat$ toge!r4 ,if ! two sub/ances lie toge!r 9 solid =m at ! bottom ( ! flask1 a v slight elevation ( temp]ature leads to ! =mation ( an extremely tr\blesome r$ sub/ance1 :i* is v difficult to remove4 ,x is almo/ impossible to remove x f ! oxidation product by recry/allization1 s9ce any consid]able am\nt ( x has a m>k$ influ5ce on ! solubility ( ! salt1 r5d]+ x mu* m soluble4 ,x p]si/s ?r\gh\t all subsequ5t trans=mations ( p>anitroor?osulphob5zoic acid1 & %\ld !re=e be c>efully avoid$4 ,otto ,fis*]#aa has %[n t 9 conc5trat$ solution1 potassium hydroxide acts on nitro d]ivatives ( tolu5e1 ) ! =mation ( v>i\s color$ sub/ances d]iv$ f /ilb5e4 ,9 ! case ( p>anitroor?otolu5esulphonic acid1 he describes ! sub/ance =m$ z possess+ a *]ry r$ color4 ,! reactions involv$ 9 its =mation are3 ,,* ,,hc ,,* _/ _/ #b;,c,h----,,s,,ok ,c,h----,,s,,ok ,,ko4,o,s----,c,h #b;,h,o _/ ,,no _/ _/-- ,o -- _/ ,n ,n -- ,o --_/ ,by oxidation ?is passes to a nitro comp\nd ( ! composition ,,hc ,,* _/ ,c,h----,,s,,ok ,,koo,s----,c,h _/ ,,no ,o,n ,x 0 no d\bt ! =mation ( sub/ances ( ?is nature t occasion$ ! color obs]v$ 9 "s ( ! oxidations4 #aa ,b]4 ,,xxvi-#bbca2 ,,xxviii-#bbha ,! only effective me?od ( sep>at+ ?is color$ sub/ance 0 f\nd to be to pass to ! neutral salt ( p>anitroor?osulphob5zoic acid1 by mak+ ! solution slightly alkal9e4 ,! salt ( ?is color$ sub/ance is also =m$ & ! two c be sep>at$ by a few recry/allizations 9 a fairly satisfactory mann]4 ,! yield 9 bo? ( ! trans=mations involv$ 9 ! prep>ation ( p>anitroor?osulphob5zoic acid does n fall f> %ort ( ! !oretical4 ,,iii4 ,prep>ation ( ! ,symmetrical ,*loride ( ,p>anitroor?osulphob5zoic ,acid4 ,?is *loride 0 fir/ sep>at$ f its unsymmetrical isom] by ,gray#ab4 ,x 0 obta9$ by all[+ a *lor(orm solution ( ! mix$ *lorides to evaporate until ! *lor(orm _h almo/ entirely disappe>$4 ,9 ! ?ick liquid s obta9$1 cry/als ( ! symmetrical *loride 7 =m$4 ,x 0 also obta9$ by apply+ ! me?od devis$ by ,bu*] 9 connection ) ! correspond+ *loride ( or?osulphob5zoic acid--i4e4 by ! action ( dilute ammonia on ! mix$ *lorides4 ,gray also f\nd t ! be/ conditions = secur+ a relatively l>ge proportion ( ! symmetrical *loride 71 ! employm5t ( z l[ a temp]ature z possible 9 ! =mation ( ! *lorides1 & ( z small an excess ( phosphorus p5ta*loride z w\ld suffice = ! reaction4 #ab ,inaug4 ,diss4 ,j4 ,h4 ,univ4 #ahie4 ,aft] _m exp]im5ts1 "u widely diff]+ conditions1 ! foll[+ me?od ( proc$ure1 embody+ ! results ( ,gray's "w1 0 adopt$4 ,dehydrat$ acid potassium salt ( p>anitroor?osulphob5zoic acid1 & phosphorus p5ta*loride1 9 ! ratio ( #dj3 #ee grams1 are br\ght toge!r 9 a mort> & intimately mix$4 ,! mixture is put into an evaporat+ di%1 & plac$ on a sulphuric acid ba?1 previ\sly heat$ to #aej4 ,z soon z ! action has be5 well />t$1 ! di% is remov$1 & ! reaction all[$ to proce$ )\t fur!r heat+4 ,:5 x is complete1 & ! cont5ts ( ! di% has cool$ d[n to ! temp]ature ( ! room1 ! oily product is p\r$ sl[ly into a salts bottle conta9+ ice wat]1 ! bottle be+ frequ5tly %ak5 dur+ ! process4 ,! %ak+ is cont9u$ ) r5ew$ portions ( wat]1 z long z ! wa% wat] is cl\dy4 ,! wat] is !n p\r$ (f1 ! br[ni% gummy *loride dissolv$ 9 *lor(orm1 & ! solution plac$ 9 a good-siz$ sep>at+ funnel4 ,ice wat] is !n add$1 & ! cont5ts ( ! funnel treat$ ) successive portions ( ammonia 7desk ammonia dilut$ "o half74 ,%ak+ is cont9u$ aft] ea* addition until ! odor ( ammonia has disappe>$1 & ice is add$ f "t to "t z may be requir$4 ,:5 x is f\nd t ! odor ( ammonia p]si/s aft] sev]al m9utes' %ak+1 ! *lor(orm lay]1 :i* is usually fill$ ) a solid sub/ance t has sep>at$ dur+ ! process1 is drawn (f1 filt]$1 & dri$ ) calcium *loride4 ,by ?is process all ( ! unsymmetrical *loride is conv]t$ into ! ammonium salt ( p>anitroor?ocyanb5z5esulphonic acid1 accord+ to ! equation3 ,c,cl _/ _/ ,o ,,cn _/ _/ _/ ,c,h----,,s #d,,nh ,c,h----,,s,,nh #b,,nh,cl4 ,,no ,,no :ile ! symmetrical *loride rema9s = ! mo/ "p un*ang$1 ?\gh "s ( x is conv]t$ into ! ammonium salt ( p>anitrob5zoic sulph9ide3 ,,co _/ ,c,o,cl _/ ,n4,,nh _/ _/ _/ ,c,h----,,s,cl #d,,nh ,c,h----,,s #b,,nh,cl4 ,,no ,,no ,x 0 f\nd t work+ 9 ?is way ! symmetrical *loride c\ld be prep>$ 9 pure condition1 free f its isom]4 ,! *lor(orm completely evaporates 9 a %ort "t leav+ f9e cry/als ( ! symmetrical *loride4 ,9 case ! evaporation is sl[ & incomplete1 x may be conclud$ t n all ( ! unsymmetrical *loride has be5 remov$4 ,! yield 0 uni=mly ab\t #dj p] c5t ( ! !oretical4 ,f ! wat] us$ to wa% ! *lorides a consid]able am\nt ( ! orig9al salt c be recov]$1 z ! reaction "u ! conditions employ$1 is nev] complete4 ,an exam9ation 0 made ( ! sub/ance m5tion$ z sep>at+ 9 ! *lor(orm solution ( ! *lorides1 dur+ ! treatm5t ) ammonia1 & x 0 f\nd to possess ! foll[+ prop]ties4 ,x is insoluble 9 b5z5e1 *lor(orm1 acetone1 e!r & ligro92 soluble 9 glacial acetic acid1 f :i* x sep>ates on cool+ 9 colorless1 cry/all9e condition2 insoluble 9 ! cold 9 wat]1 alcohol & ammonia1 b by boil+ ) ^! reag5ts1 or by long /&+ 9 ! cold1 x is dissolv$ ) decomposition4 ,x 0 dissolv$ 9 hot wat] & ! solution1 :i* 0 acid 9 reaction1 0 neutraliz$ ) potassium c>bonate4 ,on add+ an excess ( hydro*loric acid to ! solution1 & all[+ x to cool1 *>act]i/ic cry/als ( acid potassium salt ( p>anitroor?osulphob5zoic acid sep>at$4 ,^! prop]ties id5tify ! sub/ance z ! anhydride ( ?is acid4 ,! =mation ( ! correspond+ anhydride ( or?osulphob5zoic acid by ! action ( phosphorus p5ta*loride ^u its acid potassium salt 0 obs]v$ by ,sohon#ac1 :o made use ( ! reaction to prep>e ?is anhydride 9 quantity4 #ac ,inaug4 ,diss4 ,j4 ,h4 ,univ4 #ahif4 ,,iv4 ,prop]ties ( ! ,symmetrical ,*loride ( ,p>anitroor?osulphob5zoic ,acid4 ,z fir/ obta9$1 ! cry/als ( ! symmetrical *loride resemble irregul>ly %ap$ pieces ( amb]1 bo? 9 color1 & 9 lu/re4 ,on recry/allization f *lor(orm or e!r1 !y may be obta9$ p]fectly colorless1 & are (t5 ( v simple cry/allographic =m4 ,! *loride cry/allizes 9 ! monocl9ic sy/em1 & possesses a v rem>kable cry/alliz+ p[]1 9 :i* respect x diff]s noticeably =m its isom]4 ,ev5 9 *lor(orm solution t is f> f dry1 cry/als appe> ) ! greate/ ease4 ,! habit ( ! cry/als diff]s v mu* accord+ to ! conditions ( cry/allization4 ,n infrequ5tly almo/ p]fectly =m$ cry/als ( ! simple/ =m--! oblique octah$ron--7 obta9$ ?\gh = ! mo/ "p ! =m 0 mu* m complicat$1 p9acoid & dome faces1 toge!r ) basal planes be+ prom95t4 ,z a rule1 ! cry/als 7 n suitable = cry/allographic "w1 z ! faces are usually unev5 & ! edges r\nd$4 ,by prop] precautions h[ev]1 good ones 7 obta9$1 & measurem5ts ( ^! w be f\nd 9 ?is diss]tation :5 x appe>s 9 pr9t4 ,! size ( "s ( ! cry/als obta9$ 0 unusual = sub/ances ( ?is class4 ,"o cry/al obta9$ ) no special precautions1 save lett+ a solution ( ! *loride /& undi/urb$ = sev]al days1 9 a r cool place measur$ #c #b4e #a4e cm41 & weigh$ #aa4b grams4 ,! cry/als are q compact1 _! d5sity be+ abut #a4he4 ,!y melt at #ih 7uncorr47 ,! *loride is q /able 9 cry/all9e condition4 ,ev5 9 moi/ air ! cry/als 7 un*ang$1 & reta9$ _! lu/re z long z !y 7 9 my possession4 ,an analysis = *lor9e gave ! foll[+ results4 4#bbjj gram gave 4#bbab gram ,ag,cl4 ,c,o,cl _/ ,cal4 = ,c,h----,,s,cl ,,no ,f\nd4 ,cl #bd4id #bd4hc ,v4 ,! ,action ( ,b5z5e & ,alum9ium ,*loride on ! ,symmetrical ,*loride ( ,p>anitroor?osulphob5zoic ,acid4 ,hollis#ad 9 8 /udy ( ! action ( ^! reag5ts ^u ! unsymmetrical *loride1 te/$ _! action ^u "o portion ( ! symmetrical *loride1 & f\nd ! products to be id5tical 9 ! two cases4 ,a few exp]im5ts 7 made 9 confirmation ( ^! results1 & ! same products1 9 g5]al1 7 obta9$4 ,x 0 obs]v$ h[ev] t ! reactions diff] 9 ! relative ease ) :i* !y are br\ght ab\t4 ,9 ! case ( ! symmetrical *loride1 ! reaction is a mu* m vigor\s "o4 ,on add+ alum9ium *loride to a solution ( ! symmetrical *loride1 9 b5z5e1 action beg9s at once ! temp]ature ( ! h&1 & v little ext]nal heat1 & t only 9 ! latt] /ages ( ! op]ation1 is ne$ful = ! completion ( ! reaction4 ,! application ( mu* heat conv]ts all ( ! product into ?ick t>ry sub/ances f :i* no?+ satisfactory c\ld be obta9$4 #ad ,inaug4 ,diss4 ,j4 ,h4 ,univ4 #ahif4 ,:5 ! reaction 0 complete1 ! result+ product 0 isolat$ & purifi$ 9 accordance ) ! directions giv5 by ,hollis4 ,repeat$ trials %[$ t1 z 9 ! case ( ! unsymmetrical *loride1 only "o ph5yl gr\p c\ld be introduc$ by ?is me?od4 ,! result+ comp\nd1 p>anitroor?ob5zoylb5z5esulphon *loride1 0 id5tical ) t d]iv$ f ! unsymmetrical *loride4 ,ow+1 h[ev]1 to ! fact t s mu* m decomposition occurs 9 ! reaction ) ! symmetrical *loride1 9 p>anitroor?ob5zoylb5z5e sulphon *loride c\ld n be obta9$ 9 p]fectly pure condition4 ,9 appe>ance x agre$ closely ) t describ$ by ,hollis1 =m+ v *>act]i/ic gre5i%1 rhombic cry/als4 ,^! melt$1 n v %>ply1 at #agd in/ead ( #agg z obs]v$ by ,hollis4 ,accord+ly1 to e/abli% ! id5tity ( ! two comp\nds beyond any d\bt1 ! mat]ial on h& 0 conv]t$ into ! b>ium salt ( p>anitroor?ob5zoylb5z5e sulphonic acid4 ,?is 0 done by boil+ ! sulphon *loride ) dilute hydro*loric acid until complete solution _h be5 effect$2 evaporat+ to dryness on a wat]-ba?2 dissolv+ ! residue 9 hot wat]1 & neutraliz+ ) b>ium c>bonate4 ,on filt]+ ! hot solution f ! excess ( c>bonate1 & all[+ x to cool1 ! b>ium salt sep>at$4 ,! solution 0 some:at color$ by impurities1 & ! long ne$les 9 :i* ! salt cry/alliz$ 7 also some:at color$4 ,!y 7 analys$ ) ! expectation t !y w\ld prove to be specim5s ( ! salt describ$ by ,hollis z hav+ ?ree1 or ?ree & a half molecules ( wat] ( cry/allization1 9 z mu* z ! conditions "u :i* !y 7 =m$ 7 favorable to ! =mation ( salts ) ^! ratios ( wat] ( cry/allization4 ,hollis f\nd t ?is salt c\ld be obta9$ ) at lea/ f\r diff]5t ratios ( wat] ( cry/allization viz4 ?ree1 ?ree & a half1 six & sev5 molecules respectively4 ,! analysis 0 z foll[s1 ! am\nt ( b>ium be+ calculat$ on ! basis ( ! anhydr\s salt4 #j4cjhg gram lo/ #j4jfd gram at #baj1 & gave #j4jgei gram ,ba,s,o4 ,cal4 = 7,c,h,o,,ns7,ba #aa;,h,o ,f\nd4 ,h,o #bj4ij #bj4gc ,ba #ah4bi #ah4bc ,! "m-liquor1 9 :i* ! cry/als rema9+ f analysis 7 r$issolv$1 0 w>m$1 b n boil$1 ) boneblack1 to remove impurities4 ,:5 filt]$1 ! solution 0 p]fectly colorless1 & on /&+ = "s "t1 well =m$ colorless1 rhombic cry/als appe>$4 ,on analysis !y gave results z foll[s4 #j4bhjd gram lo/ #j4jdje gram at #baj1 & gave #j4jgei gram ,ba,s,o4 ,cal4 = 7,c,h,o,,ns7,ba #g;,h,o4 ,f\nd4 ,h,o #ad4dj #ad4dd4 ,ba #ah4bi #ah4jc4 ,9 mak+ a fur!r supply ( ! salt x 0 f\nd t if ! solution1 aft] filt]+ f ! b>ium c>bonate1 0 dilut$ to su* an ext5t t no cry/als sep>at$ on cool+1 !n on sl[ evaporation "u a bell-j> ! fir/ cry/als to appe> 7 v long sl5d] ne$les4 ,z evaporation proce$$1 ^! ne$les became mu* ?ick] assum+ prismatic proportions1 & correspond$ 9 appe>ance to ! salt describ$ by ,hollis z hav+ six molecules ( cry/al wat]4 ,z gr[? proce$$1 ! cry/als became d>k 9 color1 & ! "m-liquor correspond+ly cle>]1 ! cry/als evid5tly absorb+ ! impurity 9 _! gr[?4 ,:5 ! solution _h become q colorless1 rhombic cry/als ( ! salt conta9+ sev5 molecules ( wat] ( cry/allization appe>$4 ,! l>g] prismatic cry/als 7 c>efully remov$1 & r$issolv$ 9 wat] 9 ord] to see if ! same ph5om5a w\ld repeat !mselves4 ,?is 9 fact 0 ! case1 cry/als ( bo? types appe>+ 9 ! same way z describ$4 ,)\t sep>at+ ! cry/als 9 ?is second exp]im5t1 wat] 0 add$1 & ! cry/als dissolv$4 ,! solution 0 !n w>m$ briskly ) boneblack1 & filt]$4 ,f ! filtrate1 :i* 0 colorless1 no?+ b rhombic cry/als hav+ sev5 molecules ( wat] ( cry/allization c\ld be obta9$1 al?\gh a great _m v>iations 9 ! conditions 7 tri$4 ,analysis ( ^! la/ cry/als 0 z foll[s3 #j4bdjj gram lo/ #j4jce gram at #baj1 & gave #j4jfcg gram ,ba,s,o4 ,cal4 = 7,c,h,o,,ns7,ba #g;,h,o4 ,f\nd4 ,h,o #ad4dj #ad4eh ,ba #ah4bi #ah4bg ,hollis /ates t treatm5t ) boneblack decomposes ?is salt1 & h5ce he did n purify x prior to cry/allization4 ,f ! exp]im5ts j describ$ x seems probable t ! impurities pres5t affect ! cry/all9e habit1 & ! degree ( hydration ( ?is salt 9 a v /rik+ mann]4 ,by c>eful w>m+ ) boneblack no decomposition 0 obs]v$1 & ! cry/als s obta9$ h con/antly sev5 molecules ( cry/al wat]4 ,,vi4 ,! ,action ( ,alcohols ^u ! ,symmetrical ,*loride ( ,p>anitroor?osulphob5zoic ,acid4 ,ka/le#ae f\nd t :5 ! *lorides ( p>anitroor?osulphob5zoic acid 7:i* he suppos$ to be an individual7 7 dissolv$ 9 alcohol1 & ! solution boil$ = "s "t1 ! acid e!rial salt ( p>anitroor?osulphob5zoic acid 0 ! f9al product4 ,! reactions 7 %[n to be3 ,c,o,cl ,,cooc,h _/ _/ ,i4 ,c,h----,,s,cl ,c,h,,oh ,c,h----,,s,cl ,h,cl4 ,,no ,,no ,,cooc,h ,,cooc,h _/ _/ ,,ii4 ,c,h----,,s,cl ,c,h,,oh ,c,h----,,s,,oc,h ,h,cl ,,no ,,no ,,cooc,h ,,cooc,h _/ _/ ,,iii4 ,c,h----,,s,,oc,h ,c,h,,oh ,c,h----,,s,,oh 7,c,h7,o ,,no ,,no #ae ,am4 ,*4 ,j\rn4 ,,xi--#bha4 ,ka/le1 x w be obs]v$1 gave ! symmetrical =mula to ?is mixture ( *lorides4 ,sev]al acid e!rial salts 7 made1 & a s]ies ( ! neutral salts ( v>i\s metals describ$ by him4 ,! action ( pure symmetrical *loride 0 /udi$ 9 ! same g5]al mann] to see if ! result+ products w\ld be ! same z ^? =m$ f ! mix$ *lorides4 #a4 ,action ( ,me?yl ,alcohol ^u ! ,symmetrical *loride4 ,a portion ( ! *loride 0 dissolv$ 9 me?yl alcohol1 & ! solution boil$ until a drop add$ to cold wat] gave no precipitate1 ( un*ang$ *loride4 ,! alcohol 0 !n di/ill$ (f1 & ! ?ick syrup rema9+1 dilut$ ) wat]4 ,?is solution 0 neutraliz$ ) b>ium c>bonate & filt]$4 ,on cool+1 ! b>ium salt cry/alliz$ 9 %9+ mica-l plates1 or 9 yell[i% ne$les correspond+ accurately ) ^? describ$ by ,ka/le4 ,!y gave ! foll[+ analytical results4 #j4bffd gram lo/ #j4jbaa gram at #aej1 & gave #j4jhgj gram ,ba,s,o4 ,,coo* _/ ,cal4 = ,c,h----,,s,o ,ba #c;,h,o ,,no #b ,f\nd ,h,o #g4gi #g4hh anhydr\s salt ,ba #bj4he #bj4he #b4 ,9 l mann] ! b>ium e?yl salt 0 made4 ,x also agre$ p]fectly ) ,ka/le's description1 cry/alliz+ 9 f9e1 colorless ne$les1 =m+ 9 tufts f a n too conc5trat$ solution4 ,9 case x is necess>y to conc5trate ^! solutions1 x is ( advantage to add a small quantity ( alcohol to ! solution z ?is prev5ts any great am\nt ( saponification1 :i* o!rwise takes place to a noticeable ext5t4 ,analysis4 ,i4 #j4bhbd gram lo/ #j4jbgf gram at #ahj1 & gave #j4jhfj gram ,ba,s,o4 ,,ii4 #j4bfee gram lo/ #j4jbfb gram at #aij1 & gave #j4jhae gram ,ba,s,o4 ,,cooc,h _/ ,cal4 = ,c,h----,,s,o ,ba #d;,h,o4 ,,no #b ,f\nd4 ,i ,,ii ,h,o #i4ea #i4gg #i4hf ,ba #bj4jj #ai4hd #bj4jb ,ka/le also f\nd t by dissolv+ ! mix$ *lorides 9 alcohol 9 ! cold1 & all[+ ! solution to evaporate1 !re sep>at$ aft] a "t1 cry/als ( ! *loride ( ! acid e!rial salt ( p>anitroor?osulphob5zoic acid ^: =mation & composition are repres5t$ 9 equation ,i4 ,?is same product 0 s\ght = :5 pure symmetrical *loride 0 employ$1 b )\t success4 ,9 e case1 cry/als ( un*ang$ *loride sep>at$1 or else x 0 f\nd t x _h be5 completely conv]t$ into ! acid e!rial salt4 ,9 ano!r trial cold wat] 0 c>efully add$ 9 small portions1 s9ce ,ka/le f\nd t su* treatm5t facilitat$ ! sep>ation ( ! sub/ance2 ! *loride alone appe>$4 ,/ill o!r attempts 7 made to obta9 ! sub/ance by add+ a l>ge am\nt ( wat] to ! solution ( ! *loride 9 alcohol1 aft] x _h /ood = "s "t4 ,9 ?is way1 q a precipitate 0 ?r[n d[n1 & ?is 0 filt]$ (f & cry/alliz$ f e!r4 ,x always prov$ to be ! symmetrical *loride1 & none ( ! o!r sub/ance 0 obta9$4 ,k>slake#af 9 work+ ) ! symmetrical *loride ( or?osulphob5zoic acid1 0 unable to isolate ! analog\s comp\nd1 al?\gh f ! mix$ *lorides1 by ! action ( alcohols1 ,rems5 & ,dohme#ag _h obta9$ *loro-e!rial salts4 #af ,inaug4 ,diss4 ,j4 ,h4 ,univ4 #ahie4 #ag ,am4 ,*4 ,j\rn4 ,,xi1 #cda4 ,9 z mu* z ! pure symmetrical *loride is relatively /able 9 cold alcohol 7x c be cry/alliz$ f w>m alcohol ) v little loss71 x is possible t x is m /able ?an ! *loro e!rial salt1 & t 9 consequ5ce ! latt]1 :5 =m$1 yields m readily to ! fur!r action ( alcohol ?an does ! unact$ on *loride4 ,h5ce :5 ! action beg9s1 x at once proce$s to ! limit4 ,! fact t ! symmetrical *loride is r sp>+ly soluble 9 cold alcohol1 mak+ ! use ( conc5trat$ solutions impossible1 may also be a factor 9 ! case4 ,:atev] may be ! cause1 ?is sub/ance c\ld n be obta9$ "u any conditions t 7 devis$4 ,hav+ 9 my possession a v small specim5 ( cry/alliz$ unsymmetrical *loride1 x 0 submitt$ to ! action ( e?yl alcohol1 "u z ne>ly z possible ! conditions employ$ by ,ka/le4 ,cry/als ( a colorless sub/ance 7 obta9$1 :i* 9 e respect agre$ ) ,ka/le's description ( ! *loride ( ! acid e?yl e!rial salt ( p>anitroor?osulphob5zoic acid4 ,cry/alliz$ f e!r !y melt$ at #fh4 ,! conditions employ$ by ,ka/le 9 prep>+ ! *loride w\ld und\bt$ly lead to a relatively l>ge proportion ( unsymmetrical *loride1 & x is to ?is *loride t ! =mation ( ! *loro e!rial salt is app>5tly due4 ,,vii4 ,! ,action ( ,ph5ols ^u ! ,symmetrical ,*loride ( ,p>anitroor?osulphob5zoic ,acid4 ,rems5 & ,saund]s#ah 9 _! inve/igation ( ! *lorides ( or?osulphob5zoic acid1 /udi$ ! action ( ph5ol ^u ^! sub/ances1 & f bo? ! symmetrical *loride & ! mix$ *lorides1 !y obta9$ a normal diph5yl e!r toge!r ) a r$ sub/ance :i* 0 n fur!r /udi$4 ,x 0 =m$ 9 small quantity & 0 probably ! correspond+ sulphonph?ale94 ,lat] ,mc,kee#ai obta9$ ^! same sub/ances f bo? ! symmetrical & ! unsymmetrical *lorides4 ,r4 ,mey]#bj obta9$ analog\s sub/ances by ! action ( v>i\s ph5ols ^u ph?alyl *loride4 ,x seem$ probable1 !re=e1 t ! *lorides ( p>anitroor?osulphob5zoic acid w\ld yield simil> d]ivatives1 & a /udy 0 accord+ly made ( ! reaction ( ! symmetrical *loride ) a s]ies ( ph5ols4 ,! products 9 "s in/ances 7 exce$+ly difficult to deal )1 possess+ prop]ties t made x impossible to prep>e !m = analysis1 b ev5 9 su* cases !re c\ld be little d\bt z to ! g5]al nature ( ! reactions :i* _h occurr$4 #ah ,am4 ,*em4 ,j\rn4 ,,xvii1 #cdg4 #ai ,ibid4 ,,xviii1 #gih4 #bj ,b]4 ,,xxvi1 #bjd4 #a4 ,! ,action ( ,ph5ol ^u ! ,symmetrical ,*loride ( ,p>anitroor?osulphob5zoic ,acid4 ,a portion ( ! symmetrical *loride 0 br\ght toge!r ) some:at m ?an d\ble ! molecul> am\nt ( ph5ol4 ,! mixture 0 plac$ 9 a good-siz$ te/-tube & ! temp]ature gradually rais$ by means ( a sulphuric acid ba?4 ,z soon z ! ph5ol melts1 "s slight action occurs1 z is indicat$ by ! fact t ! mixture assumes a bright r$ color4 ,no appreciable am\nt ( hydro*loric acid gas is evolv$ h[ev]1 until ! liquid mixture has rea*$ a temp]ature ( ab\t #aae4 ,at ?is po9t ! gas is freely evolv$1 & ! action is complete at a temp]ature ( #abe4 ,! temp]ature obs]vations 7 made by means ( a !rmomet] us$ z a /irr+ rod 9 ! mixture4 ,dur+ ! heat+1 ! color ( ! liquid becomes a mu* m int5se r$1 gr[+ d>k] 9 %ade1 & ! liquid itself becomes some:at visc\s b does n solidify :ile hot4 ,:5 cool1 ! melt 0 repeat$ly extract$ ) boil+ wat]1 ! aque\s solution be+ v deep purple 9 color4 ,! color$ matt] 0 remov$ v sl[ly 9 ?is mann]1 & s ! process 0 cont9u$ ) dilute alkali4 ,a solid insoluble residue 0 ?us obta9$1 ( a light-br[ni% color4 ,?is 0 dissolv$ 9 alcohol1 boil$ ) boneblack & filt]$4 ,on cool+1 ne$les ( a /raw yell[ color 7 deposit$ f ! alcoholic solution4 ,?is prov$ to be ! normal diph5yl e!rial salt ( p>anitroor?osulphob5zoic acid1 ! =mation ( ?is sub/ance be+ express$ by ! equation3 ,c,o,cl ,,cooc,h _/ _/ ,c,h----,,s,cl #b;,c,h,,oh ,c,h----,,s,,oc,h #b;,h,cl4 ,,no ,,no ,analysis ( ! sub/ance gave ! foll[+ results3 ,i4 #j4afbg gram gave #j4ccih gram ,,co & #j4jeaj gram ,h,o4 ,,ii4 #j4aiii gram gave #j4dahj gram ,,co & #j4jfjj gram ,h,o4 ,,iii4 #j4bfdi gram gave #j4aefa gram ,ba,s,o4 ,,cooc,h _/ ,cal4 = ,c,h----,,s,,oc,h ,,no ,f\nd4 ,i ,,ii ,,iii ,c #eg4ad #ef4ig #eg4jc ---- ,h #c4bf #c4dg #c4cc ---- ,s #h4jb ---- ---- #h4ji ,?is sub/ance melts at #aai 7uncorr74 ,x possesses prop]ties simil> to ^? ( ! diph5yl e!rial salt ( or?osulphob5zoic acid describ$ by ,saund]s4 ,x is insoluble 9 wat]1 & is unaffect$ by hydro*loric acid or aque\s alkali4 ,on heat+ = a %ort "t ) alcoholic pota%1 ! ne$les 7 trans=m$ into a volum9\s precipitate4 ,?is 0 filt]$ (f1 dissolv$ 9 wat]1 & hydro*loric acid 0 add$4 ,on cool+1 *>act]i/ic cry/als ( ! acid potassium salt ( p>anitroor?osulphob5zoic sep>at$4 ,analysis4 #j4acib gram lo/ #j4jji gram at #aej & gave #j4jche gram ,k,,s4 ,,cooh _/ ,cal4 = ,c,h----,,s,,ok ,h,o ,,no ,f\nd4 ,h,o #e4ie ,h,o #f4ea ,k #ac4fe ,k #ac4ce ,no attempt 0 made to isolate ! correspond+ int]m$iate *lor-e!rial salt ( ! composition ,,cooc,h _/ ,c,h----,,s,cl ,,no or its acid z 0 done by ,mc,kee#ba 9 8 "w on ! analog\s e!rial salt ( or?osulphob5zoic acid4 #ba ,am4 ,*4 ,j\rn4 ,,xviii-#gii ,on evaporat+ ! aque\s extract f ! orig9al melt almo/ to dryness on ! wat]-ba?1 !re 0 a deposit on ! sides ( !di% ( scales possess+ a beautiful bronze-gre5 metallic lu/re ,!y =m$ a deep purple solution 9 alkalis1 or mag5ta1 if ! solution 0 v dilute1 & orange-yell[ 9 acids4 ,on acidify+ ! alkal9e extract ) hydro*loric acid1 ?is same sub/ance 0 precipitat$ z a br[ni% floccul5t precipitate4 ,x 01 h[ev]1 f\nd to be impossible to obta9 ?is sub/ance 9 pure condition4 ,! am\nt =m$ 9 ! reaction is small1 & its prop]ties 7 su* z to r5d] "w ) x v difficult4 ,! me?od ( precipitation is n satisfactory because1 ow+ to ! fact t ! sub/ance is soluble 9 acid solutions to an unusual ext5t = sub/ances ( ?is class1 ! solution _h to be conc5trat$ to su* a degree z to r5d] ! precipitat$ sub/ance v impure f acids & alkali salts4 ,^! c\ld n be remov$ by wa%+1 obvi\sly1 )\t aga9 dissolv+ ! sub/ance4 ,f its prop]ties h[ev]1 & its color reactions1 !re c be little d\bt t ! sub/ance is a sulphonph?alen1 & t x is always =m$ 9 consid]able quantities 9 ! reaction ( ph5ol ^u ! symmetrical *loride4 ,x 0 notic$ t ! aque\s extract ( ! mass left aft] fusion 0 almo/ always decid$ly acid 9 reaction1 & x 0 ?\ght t ?is might be due to ! =mation ( an acid e!rial salt1 ^: =mation w\ld be express$ by ! equations3 ,c,o,cl ,,cooc,h _/ _/ ,c,h----,,s,cl ,c,h,,oh ,c,h----,,s,cl ,h,cl4 ,,no ,,no ,,cooc,h ,,cooc,h _/ _/ ,c,h----,,s,cl ,h,o ,c,h----,,s,,oh ,h,cl4 ,,no ,,no ,accord+ly1 ! solution 0 saturat$ ) b>ium c>bonate1 ! excess ( c>bonate remov$ by filtration1 ! filtrate conc5trat$1 & all[$ to cool4 ,cry/als 9 ! =m ( pe>ly scales sep>at$1 :i* ^u analysis prov$ to be ! neutral b>ium salt ( p>anitroor?osulphob5zoic acid4 #j4bbia gram anhydr\s salt gave #j4achf gram ,ba,s,o4 ,,coo _/ _/ ,ba _/ _/ ,cal4 = ,c,h----,,s,o ,,no ,f\nd ,ba #ce4he #ce4eg ,?is w\ld se5 to indicate t ! reaction is an incomplete "o ev5 9 ! pres5ce ( excess ( ph5ol4 ,no indications ( ! =mation ( an acid e!rial salt 0 obs]v$4 #b4 ,! ,action ( ,or?ocresol ^u ! ,symmetrical ,*loride ( ,p>anitroor?osulphob5zoic ,acid4 ,) or?ocresol ! reaction proce$s ) m difficulty4 ,a high] temp]ature 0 requir$ 7#ace-ade71 & q an am\nt ( t>ry mat]ial 0 obta9$ f :i* v little c\ld be extract$4 ,! product 0 w>m$ repeat$ly ) dilute alkali1 ! solution s obta9$ neutraliz$ ) hydro*loric acid1 & di/ill$ ) /eam = sev]al h\rs to free x f cresol4 ,! result+ solution 0 !n evaporat$ to small volume1 & acidifi$ ) hydro*loric acid4 ,a consid]able precipitate 0 ?r[n d[n1 :i* 0 easily filt]$ (f & dri$4 ,9 ?is condition x is a d>k purple-r$ p[d]1 lumps ( :i* possess$ a yell[i%-bronze metallic lu/re4 ,9 dilute alkal9e solution x =ms a deep-blui% purple solution1 :ile 9 acids x is crimson1 or light yell[ if ! solution is dilute4 ,x is a excell5t indicator1 especially ) ammonia4 ,9 ! insoluble t>ry sub/ance ! e!rial salt 0 s\ght = & obta9$ 9 small quantity only4 ,z ?is sub/ance is soluble 9 alcohol1 & sep>ates aga9 on cool+ 9 mu* ! same condition1 ! e!rial salt c\ld n be isolat$ be cry/allization f ?is solv5t4 ,by boil+ ! sub/ance ) b5z5e1 purify+ ! filtrate ) boneblack1 & all[+ ! b5z5e to evaporate1 an almo/ colorless gummy sub/ance 0 obta9$1 :i* :5 dissolv$ 9 alcohol1 cry/allizes 9 small colorless ne$les :i* melt at #hi-ij4 ,!y 7 n obta9$ 9 quantity suffici5t = analysis1 b !re 0 little d\bt t !y 7 cry/als ( ! dior?ocresol e!rial salt4 ,app>5tly mu* m decomposition occurr$ 9 ?is reaction ?an :5 p>acresol 0 employ$1 probably 9 consequ5ce ( ! high] temp]ature requir$ = ! reaction4 #c4 ,! ,action ( ,p>acresol ^u ! ,symmetrical ,*loride ( ,p>anitroor?osulphob5zoic ,acid4 ,?is reaction 0 conduct$ 9 ! same mann] z ) ph5ol4 ,no hydro*loric acid 0 evolv$ until a temp]ature ( ab\t #aaj 0 rea*$1 al?\gh aft] melt+1 ! solution _h /eadily d>k5$ to a deep r$di%-br[n color4 ,at #acj1 aft] heat+ = sev]al h\rs1 hydro*loric acid ceas$ to be evolv$4 ,! product 0 treat$ z 9 ! la/ exp]im5t4 ,! alkal9e extract did n exhibit any m>k$ color reactions1 su* z 7 obs]v$ 9 mo/ ( ^! exp]im5ts1 be+ dull r$di%-br[n 9 bo? acid & alkal9e solution4 ,! insoluble residue cry/alliz$ f alcohol 9 light br[n transp>5t cry/als1 :i* did n lose _! color by repeat$ cry/allization1 & boil+ ) boneblack1 & melt$ %>ply at #aag4 ,f b5z5e !y cry/alliz$ 9 colorless ne$les or flat1 n>r[ plates4 ,^! become opaque on exposure to ! air1 app>5tly ?r\gh loss ( b5z5e ( cry/allization4 ,analysis ( ! ne$les f alcohol gave ! foll[+ results3 ,i4 #j4bcgb gram ( sub/ance gave #j4eacg gram ,,co & #j4jife gram ,h,o4 ,,ii4 #j4bbbc gram gave #j4abjc gram ,ba,s,o4 ,,cooc,h4,,* _/ ,cal4 = ,c,h----,,s,,oc,h4,,* ,,no ,f\nd4 ,i ,,ii ,c #ei4jh #ei4jf ,h #c4ih #d4eb ,s #g4di #g4dc #d4 ,! ,action ( ,hydroqu9one ^u ! ,symmetrical ,*loride ( ,p>anitroor?osulphob5zoic ,acid4 ,action ) hydroqu9one occurs at #abj-ace1 ! mixture at ! same "t becom+ d>k color$ & visc\s4 ,on cool+1 ! product 0 p[d]$ & treat$ ) dilute alkali4 ,x readily dissolv$1 )\t residue1 =m+ a d>k r$ solution4 ,9 conc5trat$ solution ! addition ( acid produces a volum9\s precipitate1 d>k br[n 9 color1 :i* :5 wa%$1 & dri$ 9 pap] =ms an almo/ black p[d]4 ,a dilute solution ( ?is p[d] is d>k r$ :5 alkal9e1 orange-yell[ :5 acid4 ,f ! way 9 :i* ?is p[d] 0 obta9$1 & ow+ to ! fact t its solubility prev5t$ repeat$ wa%+1 x 0 evid5t t x w\ld n give close analytical results = a calculat$ =mula4 ,x 0 ?\ght1 h[ev]1 t analysis w\ld give a g5]al idea ( ! composition4 ,analysis ( diff]5t specim5s gave results = sulphur :i* av]ag$ ab\t #e4e4 ,! p]c5tage requir$ = ! =mula ,c,c,h7,,oh7 _/ _/ ,o _/ _/ ,c,h----,,s ,,no :i* repres5ts ! simple/ sulphonfluorescen1 is #g4dc4 ,! comp\nd c\ld h>dly h be5 s f> f pure z to occasion su* a discrepancy 9 results z ?is4 ,x w\ld appe>1 !re=e1 t m ?an two molecules ( hydroqu9one ent] into ! reaction ) "o molecule ( ! *loride4 ,%\ld f\r molecules be involv$ 9 ! reaction1 lead+ to a comp\nd ( "s su* =mula z ,c,c,h7,,oh7 _/ _/ ,o _/ _/ ,c,h----,,s,c,h7,,oh7 ,,no ! !oretical p]c5tage ( sulphur w\ld be #f4jj :i* corresponds mu* m closely ) ! results obta9$4 ,?is is 9 accord ) ! obs]vations ( a numb] ( work]s 9 ?is laboratory--,lyman1 ,gilp91 ,l9n & o!rs--:o h work$ on v>i\s sulphonfluorescens1 & h f\nd t 9 _m cases f\r1 six & ev5 eight ph5ol residues cond5se ) "o molecule ( ! anhydr\s acid4 ,lyman#bb especially describes a tetra hydroqu9one sulphonfluorescen d]iv$ f or?osulphop>atoluic acid4 ,no e!rial salt 0 obs]v$4 #bb ,am4 ,*em4 ,j\rn4 ,,xvi-#ebe #e4 ,! ,action ( ,resorc9 ^u ! ,symmetrical ,*loride ( ,p>anitroor?osulphob5zoic ,acid4 ,! reaction ( resorc9 ) ! *loride is a mu* clean] "o & proce$s m easily ?an 9 ! case j describ$1 lead+ app>5tly to an individual comp\nd :i* is well *>act]iz$4 ,dur+ ! reaction1 :i* is complete at #abe1 ! mixture becomes almo/ p]fectly solid1 & :5 cool1 x is q brittle4 ,x 0 r$uc$ to a r$di% p[d] 9 a mort> & dissolv$ 9 sodium hydroxide1 !re be+ no insoluble residue4 ,by ! addition ( hydro*loric acid1 ! sulphonfluorescen 0 ?r[n d[n z a *ocolate-br[n precipitate1 :i* 0 filt]$ (f1 wa%$ to neutral reaction on a filt]1 & dri$ on pap]4 ,9 ?is condition x is a light *ocolate-br[n p[d]4 ,9 dilute alkal9e solution x possesses a slight fluoresc5ce be+ p9k by transmitt$ & yell[ be reflect$ light1 sugge/+ eos9 9 a g5]al way4 ,x is int]e/+ to note t ! sulphonfluorescen ( or?osulphob5zoic acid possesses a fluoresc5ce t c h>dly be di/+ui%$ f ord9>y fluorescen & t ! introduction ( a nitro gr\p into ! acid residue produces mu* ( ! same effect z d ! f\r brom9e atoms 9 eos94 ,9 acid solution ! color is r$di%-orange4 ,analysis ( ! comp\nd1 prep>$ z above describ$1 gave ! foll[+ results4 ,i4 #j4agde gram gave #j4ccci gram ( ,,co & #j4jei gram ,h,o4 ,,ii4 #j4adfg gram gave #j4bhbj gram ,,co & #j4jdcb gram ,h,o4 ,,iii4 #j4agcb gram gave #j4ccde gram ,,co & #j4jega gram ,h,o4 ,,iv4 #j4bjjj gram gave #j4aajd gram ,ba,s,o4 ,v4 #j4aeje gram gave #j4jhbj gram ,ba,s,o4 ,,oh _/ ,c,c,h _/ _/ ,o ,,oh #b _/ _/ ,cal4 = ,c,h----,,s ,,no ,f\nd ,i ,,ii ,,iii ,,iv ,v ,c #eb4ff #eb4ah #eb4db #eb4fg ---- ---- ,h #c4df #c4gf #c4bg #c4ff ---- ---- ,s #g4ci ---- ---- ---- #g4eg #g4dh ,an ef=t to obta9 ! anhydride 0 unsuccessful4 ,"s loss ( weight 0 obs]v$1 b ! comp\nd und]w5t decomposition be=e ?is loss am\nt$ to mu*4 #f4 ,! ,action ( ,pyrogallol ^u ! ,symmetrical ,*loride ( ,p>anitroor?osulphob5zoic ,acid4 ,! product ( ?is action dissolves readily 9 dilute sodium hydroxide )\t residue1 produc+ a v deep purple-black color :5 conc5trat$1 pass+ to grayi%-violet z ! solution is dilut$4 ,on add+ hydro*loric acid1 precipitation occurs1 z 9 mo/ ( ^! reactions4 ,on attempt+ to filt] (f ?is precipitate1 x =ms a /icky1 black mass on ! filt] ) :i* little c be done4 ,x is be/ to evaporate to dryness be=e filtration & p[d] ! residue4 ,?is p[d] c !n be wa%$ fairly clean f alkali salts & acid4 ,no?+ to sugge/ ! =mation ( an e!rial salt 0 obs]v$4 ,analysis ( ?is product = sulphur %[$ t 9 ?is gallen1 z 9 ! case ( ! hydroqu9one ph?alen m ?an two pyrogallol residues _h ent]$ ! acid residue4 ,! indications 7 t six _h ent]$ into "o ( ! *loride4 ,?is also agrees ) ! obs]vation ( ,lyman#bc1 :o describes a hexapyrogallol gallen ( or?osulphop>atoluic acid4 ,probably a mixture ( v>y+ composition 0 obta9$1 & little importance 0 atta*$ to ! results save z !y %[$ t no e!rial salt is =m$ 9 ! reaction4 #bc ,am4 ,*4 ,j\rn4 ,,xvi-#ebg4 #g4 ,! ,action ( -,naph?ol ^u ! ,symmetrical ,*loride ( ,p>anitroor?osulphob5zoic ,acid4 ,x 0 hop$ t "h1 z 9 ! case ( ! monohydroxy ph5ols an e!rial salt w\ld be obta9$4 ,x 0 f\nd1 h[ev]1 t v little action occurr$1 save su* z 0 indicat$ by ! developm5t ( a bright c>m9e color 9 ! melt$ mixture1 until a temp]ature ( ab\t #afj 0 rea*$4 ,at ?is po9t hydro*loric acid 0 evolv$1 b ! *loride itself und]goes decomposition4 ,no?+ def9ite c\ld be isolat$ among ! reaction products1 save un*ang$ -,naph?ol4 ,,viii4 ,! ,action ( ,anil9e ^u ! ,symmetrical ,*loride ( ,p>anitroor?osulphob5zoic ,acid4 ,z has be5 po9t$ out 9 ! ,introduction1 x 0 9 connection ) ! anil9e d]ivatives ( or?osulphob5zoic acid1 t ! isom]ism ( ! *lorides 0 fir/ notic$1 two anilids be+ obta9$4 ,accord+ly1 :5 ,gray began 8 /udy ( ! *lorides ( p>anitroor?osulphob5zoic acid1 8 fir/ ef=t 0 to obta9 evid5ce ( ! exi/5ce ( two anilids4 ,^! 7 n obta9$1 h[ev]1 until aft] ! *lorides !mselves _h be5 isolat$1 z _! prop]ties made _! isolation & prep>ation a matt] ( difficulty4 ,"s po9ts /ill rema9$ 9 d\bt aft] ,gray's /udy1 & a fur!r inve/igation 0 ?\ght to be desirable to cle> ^! up4 ,"s "t 0 sp5t 9 an endeavor to obta9 a me?od by :i* a good yield ( fusible1 or symmetrical1 anilid c\ld be obta9$4 ,! yield 9 all cases tri$1 is n a good "o4 ,! pres5ce ( ! nitro gr\p appe>s to complicate ! reaction1 lead+ to second>y reactions ^: c\rse c\ld n be foll[$4 ,^u br++ anil9e & ! *loride toge!r1 a v vivid r$ color 0 always obs]v$1 & ! same 0 true :5 x 0 necess>y to employ alkali4 ,! fact t su* colors develop :5 nitro comp\nds are treat$ ) alkali has be5 notic$ 9 _m in/ances & "s progress has be5 made 9 ! /udy ( ^! comp\nds4 ,jackson & ,ittn]#bd h lately review$ ?is subject4 ,if a solution ( ! symmetrical *loride 9 e!r is sl[ly add$ to a simil> solution ( anil9e1 no appreciable am\nt ( heat is evolv$4 ,if ! result+ solution is all[$ to /& at ord9>y temp]atures1 action proce$s v sl[ly1 anil9e hydro*loride be+ precipitat$ z ! reaction proce$s4 ,?is c be filt]$ (f f "t to "t & ! rate ( action s obs]v$4 ,9 su* a way x 0 f\nd t five grams ( *loride requir$ ab\t fifty h\rs "t to react completely ) an excess ( anil9e4 ,simil> results 7 obta9$ ) *lor(orm z ! solv5t4 ,by boil+ ! solution = an h\r or m ! reaction is complete4 #bd ,am4 ,*em4 ,j\rn4 ,,xix-#aii ,! me?od employ$ 0 to br+ ! *loride & an excess ( anil9e--some:at m ?an f\r molecules--toge!r 9 *lor(orm solution4 ,! flask 0 !n boil$ = ab\t an h\r1 :5 ! *lor(orm 0 di/ill$ (f4 ,dur+ ! boil+ z well z ! di/illation m or less bump+ occurs 9 consequ5ce ( ! anil9e hydro*loride :i* sep>ates1 & con/ant %ak+ ( ! flask is sometimes necess>y4 ,! residue :i* is 9 a ?ick1 gummy condition 9 consequ5ce ( ! pres5ce ( an excess ( anil9e1 0 dige/$ ) wat] acidulat$ ) hydro*loric acid4 ,! excess ( anil9e is ?us remov$1 & ! reaction product obta9$ z a r$di%-br[n solid sub/ance4 ,?is 0 treat$ ) dilute sodium hydroxide1 all lumps be+ brok5 up ) a /irr+ rod4 ,! undissolv$ sub/ance is l>gely anil1 :i* 0 filt]$ (f4 ,! anilid 0 !n rega9$ by acidify+ ! alkal9e solution1 9 :i* x 0 dissolv$4 ,x sep>ates imm$iately z a curdy colorless precipitate1 ?\gh x is frequ5tly color$ p9k by impurity4 ,x 0 f\nd t ?is color c\ld be remov$1 9 case n mu* 0 pres5t1 by r$issolv+ ! anilid 9 alkali1 & sl[ly p\r+ ! solution into an excess ( dilute acid4 ,9 all cases a consid]able am\nt ( anil 0 obta9$1 ev5 :5 ! sub/ances 7 employ$ 9 ! molecul> ratios ( #a3aj4 ,! reactions involv$1 s f> z ! =mation ( anilid & anil are conc]n$ are1 ,c,o,cl ,,co4,,nh4,c,h _/ _/ ,c,h----,,s,cl #d;,c,h,,nh ,c,h----,,s4,,nh4,c,h ,c,h,,nh,cl ,,no ,,no ,,co _/ ,c,o,cl _/ ,n4,c,h _/ _/ _/ ,c,h----,,s,cl #c;,c,h,,nh ,c,h----,,s #b;,c,h,,nh,cl ,,no ,,no ,on ! :ole ! reaction seem$ to be ! mo/ satisfactory 9 *lor(orm solution1 ! ma9 objection be+1 t1 ow+ to ! simultane\s pres5ce ( *lor(orm1 alkali1 an a trace ( anil9e1 ph5yl isocyanide is always =m$1 & r5d]s ! "w m or less unpleasant4 ,a numb] ( exp]im5ts 7 also made to see if ! yield c\ld be increas$ be employ+ a modification ( ! 8,s*ott5-,baumann ,reaction0#be = ! =mation ( anilids4 ,= ?is purpose an e!rial solution ( ! *loride 0 add$ to a l solution ( anil9e 9 :i* 0 susp5d$ f9ely p[d]$ anhydr\s potassium c>bonate4 ,! proportions ( ! sub/ances 7 ^? dem&$ by ! equation ,c,o,cl ,,co4,,nh4,c,h _/ _/ ,c,h----,,s,cl #b;,c,h,,nh #b,k,cl ,c,h----,,s,,nh4,c,h #b,k,cl #b,,khco ,,no ,,no ,v little anilid 01 h[ev] obta9$1 b 9 its place a sub/ance soluble 9 wat]1 ( acid reaction capable ( =m+ salts & yield+ sev]al well *>act]iz$ d]ivatives4 ,i hope to inve/igate ?is reaction m fully at "s future "t4 #be ,b]4 ,,xvii-#bede2 ,,xxiii1 #cdcj4 99 99 99 99 99 ,! anilid is r sp>+ly soluble 9 alcohol1 f :i* x is deposit$ on cool+ 9 v small ne$les4 ,^! melt1 z /at$ by ,gray1 at #bbb4 ,x is also soluble 9 *lor(orm & glacial acetic acid1 b does n =m well def9$ cry/als f any solv5t4 ,x dissolves 9 dilute alkali f :i* solution acids precipitate x un*ang$4 99 99 99 99 99 ,! anil is also soluble 9 alcohol1 glacial acetic acid etc4 ,x cry/allizes 9 mu* bett]-=m$ cry/als ?an does ! anilid4 ,^! melt at #ahh4 ,on boil+ ! anil ) anil9e = a "t1 x is conv]t$ into ! anilid ,,co _/ _/ ,n4,c,h ,,co4,,nh4,c,h _/ _/ _/ ,c,h----,,s ,c,h,,nh ,c,h----,,s,,nh4,c,h ,,no ,,no ,9 none ( ^! reactions 0 any infusible anilid obs]v$4 ,,ix4 ,! ,action ( ,phosphorus ,oxy*loride ^u ! ,fusible ,anilid4 ,hunt]#bf f\nd t :5 ei!r ( ! anilids ( or?osulphob5zoic acid 7 treat$ ) phosphorus oxy*loride1 or simil> dehydrat+ ag5ts1 a molecule ( wat] 0 ab/ract$ ) ! =mation ( a new sub/ance4 ,a c>eful /udy ( ! comp\nd l$ to ! belief t x 0 a dianil1 & t its =mation & /ructure c\ld be repres5t$ by ! equation ,c,n4,c,h _/ ,,co4,,nh4,c,h _/ _/ _/ 4,n4,c,h ,c,h ,c,h _/ ,h,o4 _/ ,,s,,nh4,c,h ,,s ,a correspond+ /udy ( ! fusible anilid ( p>anitroor?osulphob5zoic acid 0 und]tak54 ,! me?od employ$ 9 ?is /udy 0 z foll[s4 ,a tubulat$ retort ( conv5i5t size 0 fus$ onto ! inn] tube ( a small cond5s]4 ,?is 0 done to avoid connections1 :i* are ne>ly always attack$ by ! oxy*loride4 ,ano!r satisfactory plan is to h ! neck ( ! retort ( ! same size z ! inn] tube ( ! cond5s]4 ,! ends are plac$ 9 contact1 & ! tubes b\nd 9 position by wrapp+ ) asbe/os pap]4 ,ov] ! jo9t s made1 a tight rubb] tube is drawn4 #bf ,am4 ,*4 ,j\rn4 ,,xviii-#haj4 ,a conv5i5t am\nt ( phosphorus oxy*loride 7#ej c4c47 0 plac$ 9 ! retort & ! anilid 7#e gr47 add$ ?r\gh ! tubulus4 ,on boil+1 ) ! cond5s] inv]t$1 ! anilid soon dissolv$1 ) evolution ( hydro*loric acid gas1 & ! solution became bright yell[ 9 color1 sometimes incl9+ to orange4 ,! boil+ 0 cont9u$ z long z hydro*loric acid 0 giv5 (f4 ,! oxy*loride 0 !n di/ill$ (f "u dim9i%$ pressure1 c>e be+ tak5 to %ake ! retort con/antly dur+ ! di/illation z viol5t bump+ is almo/ sure to occur especially t[>ds ! end ( ! op]ation4 ,! product rema9+1 spatt]$ ov] ! walls ( ! retort1 0 a gre5i% yell[ solid4 ,wat] 0 !n add$1 & ! :ole all[$ to /& = an h\r or s to ?or\ghly dissolve ! phosphoric acid =m$ 9 ! reaction4 ,9 case ! anilid is n p]fectly dry1 a mu* m en]getic reaction occurs1 & on di/ill+ (f ! oxy*loride1 ! product rema9s z a d>k1 gummy mass4 ,?is %\ld be spread out on ! sides ( ! retort :ile /ill liquid4 ,on cool+ & add+ wat]1 ?is gum gradually disappe>s1 & 9 its place is f\nd ! yell[ solid product j describ$4 ,! gum appe>s to be a solution ( ?is sub/ance 9 phosphoric acid4 ,aft] ! sub/ance is filt]$ (f & dri$1 x c be cry/alliz$ f acetone1 b5z5e1 glacial acetic acid or alcohol4 ,f ^! solv5ts x cry/allizes 9 small yell[ ne$les resembl+ qu9one 9 appe>ance4 ,! cry/als obta9$ =m acetone are r l>g] ?an ^? f ! o!r solv5ts1 & are m ne>ly orange 9 color1 app>5tly because ( _! great] compactness4 ,:5 glacial acetic acid is us$1 c>e mu/ be tak5 to avoid any unnecess>y heat+1 z cont9u$ heat+ produces a *ange t w pres5tly be describ$4 ,! sub/ance melts at #bjh4 ,analysis ( ! sub/ance result$ z foll[s3 ,i4 #j4chbb gram gave #j4hccd gram ,,co & #j4abgb gram ,h,o4 ,,ii4 #j4bfde gram gave #j4ehab gram ,,co & #j4jiaj gram ,h,o4 ,,iii4 #j4bjbc gram gave #j4abhc gram ,ba,s,o4 ,,iv4 #j4bjfa gram gave #j4abhj gram ,ba,s,o4 ,v4 #j4ahec gram gave #af4gc ,c4,c4,n 7,/&>d74 ,c,n4,c,h _/ _/ 4,n4,c,h _/ _/ ,cal4 = ,c,h----,,s ,,no ,f\nd4 ,i ,,ii ,,iii ,,iv ,v ,c #fj4aa #ei4dg #ei4ic ---- ---- ---- ,h #c4dd #c4fi #c4hb ---- ---- ---- ,s #h4de ---- ---- #h4gj #h4eb ---- ,n #aa4jh ---- ---- ---- ---- #aa4ce ,= analyses ,i amp2 ,,ii ,i am indebt$ to ,mr4 ,nakaseko1 :o k9dly made !m = me4 ,x4 ,! ,action ( ,reag5ts ^u ! ,dianil ( ,p>anitroor?osulphob5zoic ,acid4 #a4 ,! ,action ( ,hydro*loric ,acid on ! ,dianil ,:5 ! dianil is boil$ = "s "t ) conc5trat$ hydro*loric acid1 ! yell[ color ( ! sub/ance disappe>s1 & ! dianil is conv]t$ into a colorless sub/ance )\t1 h[ev]1 pass+ into solution4 ,! sub/ance s obta9$ 0 filt]$ (f1 & cry/alliz$ f alcohol4 ,x cry/alliz$ 9 small colorless ne$les1 :i* melt$ at #ahc1 & possess$ all ! prop]ties ( ! anil1 :i*1 9 fact1 x prov$ to be4 ,! reaction 0 !re=e ,c,n4,c,h ,,co _/ _/ _/ ,n4,c,h _/ ,n4,c,h _/ _/ _/ _/ ,c,h----,,s ,h,cl ,h,o ,c,h----,,s ,c,h,,nh,cl ,,no ,,no ,?is reaction also expla9s ! fact t "s anil 0 always obta9$ 9 mak+ ! dianil f ! anilid4 ,hydro*loric acid is =m$ 9 ! reaction1 & 9 turn acts on ! dianil 9 ! s5se ( ! equation j giv54 #b4 ,! ,action ( ,alcoholic ,pota% on ! ,dianil4 ,on boil+ ! dianil ) alcoholic pota% = a "t1 ! solution turn$ r$1 & no?+ b t>ry products 7 obta9$4 ,9 ?is respect ! dianil diff]s f ! dianil ( or?osulphob5zoic acid1 :i* "u simil> conditions1 is trans=m$ into infusible anilid4 ,?is obs]vation is1 h[ev]1 9 keep+ ) ! fact t ! nitro d]ivative1 is 9 g5]al mu* less /able 9 ! pres5ce ( alkali4 #c4 ,! ,action ( ,glacial ,acetic ,acid on ! ,dianil4 ,:5 ! dianil is boil$ ) glacial acetic acid = "s "t1 ! color ( ! solution *anges to a mu* light] %ade ( yell[1 or becomes colorless4 ,on evaporat+ ! solution to small volume1 & all[+ x to cool1 a colorless sub/ance sep>ates4 ,?is is infusible anilid4 ,x c\ld n be obta9$ 9 cry/als f any solv5t1 b always sep>at$ 9 flakes4 ,x does n melt or und]go *ange at #cdj4 ,l ! fusible anilid x dissolves 9 dilute alkali1 b on acidify+ ! solution x does n imm$iately reappe>4 ,aft] /&+ = "s "t1 h[ev]1 x gradually sep>ates 9 p]fectly pure =m4 ,9 ?is p>ticul> my obs]vation diff]s f t ( ,gray1#bg :o /ates t ?is anilid is decompos$ by solution 9 alkali4 #bg ,inaug4 ,diss4 ,j4 ,h4 ,unis4 #ahie4 ,a specim5 t _h be5 repeat$ly precipitat$ gave ! foll[+ results on analysis4 ,i4 #j4afjg gram gave #ac4hh ,c4,c4,n4 7/&>d74 ,,ii4 #j4baie gram gave #j4abhe gram ,ba,s,o4 ,,iii4 #j4aceg gram gave #j4jhjg gram ,ba,s,o4 ,c,,nh4,c,h _/ _/ ,o _/ _/ ,cal4 = ,c,h----,,s ,,no ,f\nd4 ,i4 ,,ii4 ,,iii4 ,n #aj4eh #aj4he ---- ---- ,s #h4jf ---- #h4jj #h4af ,by ?is s]ies ( trans=mations x is possible to pass f "o anilid to ! o!r1 ! /eps be+3 ,,co4,,nh4,c,h ,c,n4,c,h ,c,,nh4,c,h _/ _/ _/ _/ _/ ,n4,c,h _/ ,o _/ _/ _/ _/ _/ ,c,h----,,s,,nh4,c,h ,c,h----,,s ,c,h----,,s ,,no ,,no ,,no ,?is is ( special int]e/ z af=d+ a means ( pass+ f a d]ivative ( "o ( ! *lorides1 to a sub/ance d]iv$ f ! o!r1 by /eps t c be cle>ly foll[$4 ,conclusions4 ,9 ! c\rse ( ?is inve/igation sev]al facts h be5 e/abli%$4 #a4 ,by ! me?ods describ$1 ! symmetrical *loride ( p>anitroor?osulphob5zoic acid c be obta9$ 9 f9e cry/all9e =m1 p]fectly free f its isom]1 ) an av]age yield ( =ty p]c5t4 #b4 ,by treatm5t ( ! *loride ) b5z5e & alum9ium *loride1 only "o *lor9e atom c be replac$ by a ph5yl gr\p4 #c4 ,! b>ium salt ( p>anitroor?ob5zoyl b5z5esulphonic acid1 :5 p]fectly pure1 cry/allizes con/antly ) sev5 molecules ( wat] ( cry/allization4 #d4 ,) alcohols1 ! symmetrical *loride yields directly ! acid e!rial salt ( p>anitroor?osulphob5zoic acid1 no evid5ce hav+ be5 obta9$ ( an int]m$iate *loro-e!rial salt4 ,! unsymmetrical *loride on ! o!r h& yields ! int]m$iate product4 #e4 ,) ph5ols1 two s]ies ( d]ivatives are obta9$4 7#a7 ,) monohydroxy ph5ols1 bo? e!rial salts & sulphonph?alens are =m$1 ! =m] pr$om9at+4 7#b7 ,) polyhydroxy ph5ols no e!rial salts 7 obta9$1 b comp\nds ( ! unsymmetrical type1 usually conta9+ m ?an two ph5ol residues4 #f4 ,) anil9e an anil & an anilid ( symmetrical con/itution are =m$4 #g4 ,) phosphorus oxy*loride1 ! anilid1 by loss ( wat]1 =ms a dianil4 #h4 ,?is dianil und]goes trans=mation ) 7#a7 ,glacial acetic acid1 =m+ an anilid ( unsymmetrical con/itution4 7#b7 ,hydro*loric acid =m+ ! anil4 7#c7 ,alcoholic pota%1 ) ! =mation ( color$ decomposition products4 ,biographical4 ,! au?or ( ! =ego+ diss]tation 0 born at ,wilk9sburg1 ,pa41 ,jan4 #bi41 #ahgj4 ,ow+ to prolong$ sickness 9 *ildhood 8 education1 prior to ent]+ college1 0 mu* int]rupt$1 & 0 l>gely conf9$ to in/ruction receiv$ at home4 ,9 ! fall ( #ahhg he ent]$ ,woo/] ,univ]sity 7,ohio71 f :i* in/itution he receiv$ ! degree ( ,ba*elor ( ,arts 9 #ahia4 ,! two foll[+ ye>s 7 sp5t z a tea*] ( ,sci5ces 9 ! ,college ( ,emporia 7,kansas74 ,9 #ahic he ent]$ ! ,johns ,hopk9s ,univ]sity :]e he has s9ce be5 a /ud5t ( *emi/ry1 ) physics & ma!matics z subord9ate /udies4 ,9 #ahie he 0 appo9t$ ,univ]sity ,s*ol> 9 ,*emi/ry4 ,dur+ #ahie-f he s]v$ z lecture assi/ant to ,pr(4 ,rems5 & ,dr4 ,r5\f 9 ! und]graduate c\rses4 ,9 ! spr+ ( #ahif he 0 appo9t$ ,fell[ = ! pres5t ye>4