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The Cannizzaro Reaction Heather Jost Lab Partners: Jasmina Salcinovic & Tracey Gordineer CHEM26 2L L!

ise Stran"e de Soria Geor"ia Perimeter Colle"e #ovember $ 2%%

The Cannizzaro Reaction Resources: Mayo$ Pi&e$ Tr!m'er$ Stran"e de Soria( Microscale )r"anic Laboratory( #e* +or&: John ,iley and Sons$ 2%%2( Stran"e de Soria$ L!ise( -St!dent S!rvival G!ide.( htt'://***("'c(ed!/0lstran"e/26 2lab/s!rvival"!ide/"ri"nard2('d1( 2%% ( Purpose: The '!r'ose o1 this e2'eriment is to o2idi3e and red!ce an aromatic aldehyde to 1orm ben3oic acid and ben3yl alcohol( ,e *ill also se'arate the layers into t*o 'rod!cts$ a carbo2ylic acid and a ne!tral alcohol( Summary of the Theory behind the Cannizzaro Reaction: The Canni33aro reaction consists o1 an o2idation4red!ction reaction bet*een a hydro2ide ion and aldehydes *itho!t 54hydro"en atoms( ,ith the 'resence o1 a stron" base$ the 1irst aldehyde molec!le red!ces to a second aldehyde molec!le and then becomes a 'rimary alcohol( ,ithin this 'rocess the molec!le o2idi3es itsel1 to the corres'ondin" carbo2ylate anion( 61 the aldehyde does 'ossess an 54hydro"en atom$ the 54carbon *ill de'rotonate *hen there is a base 'resent and the reaction *ill not "o thro!"h this &ind o1 reaction 7an 8ldol reaction *ill !s!ally occ!r *ith the res!ltin" enolate9( The mechanism o1 this reaction ha''ens as 1ollo*s:

Reaction Analysis: ;alanced Chemical E<!ation: 7ClC=H>)92 ? @)H ? H? A ClC=H )H ? ClC=H )2H

Theoretical yield: 8lcohol Layer B9 Ta&e the amo!nt o1 4chloroben3aldehyde and divide it by its molec!lar *ei"ht %(C" D B %(>="/mol E %(%%2mol

29 Ta&e the val!e 1o!nd in ste' B and m!lti'ly it by the molec!lar *ei"ht o1 the 'rod!ct 8cid Layer B9 Ta&e the val!e 1o!nd in ste' B o1 alcohol layer and m!lti'ly it by the molec!lar *ei"ht o1 the 'rod!ct %(%%2mol 2 B 2(2>"/mol E 0.28"! theoretical yield %(%%2mol 2 B (>2"/mol E 0.28 ! theoretical yield

Potential side 'rod!cts: Le1tover startin" material

Procedure: 8dd B>%m" o1 4chloroben3aldehyde and %( mL o1 methanol to a >mL conical vial on a re1l!2 condenser *ith a s'in vane( Gently stir *hile addin" %( mL o1 BBM @)H( F!n the *ater thro!"h the condenser and heat *hile stirrin" bet*een 6>oC G =>oC 1or one ho!r( Cool to room tem'erat!re and add 2mL o1 cold deioni3ed *ater to the sol!tion in a se'eratory 1!nnel( E2tract the sol!tion *ith C 'ortions o1 %(>mL o1 methylene chloride( +o! sho!ld see the layers be"in to 1orm( The carbo2ylic acid is in the *ater layer and the alcohol is in the methylene chloride layer( ;oth layers sho!ld be stored !ntil the 1ollo*in" *ee&( To recover the '4chloroben3yl alcohol$ ta&e the methylene chloride layer and *ash it *ith t*o 'ortions o1 %(2>mL o1 B%H sodi!m carbonate and %(>mL o1 *ater 7this *ill ne!trali3e the sol!tion o1 resid!al acid9( )nce the layer has been e2tracted$ dry it *ith abo!t B>%m" o1 "ran!lar anhydro!s sodi!m s!l1ate( 8llo* the 'rod!ct to dry and collect 'rod!ct *ei"ht and meltin" 'oint( To recover the '4chloroben3oic acid add 2mL o1 deioni3ed *ater and a''ro2imately %( mL o1 concentrated HCl !ntil the sol!tion is acidic( Iiltrate *ith a Hirsh 1!nnel and collect the *hite 'reci'itate$ allo* the 'rod!ct to dry and "ather its meltin" 'oint and *ei"ht( #bser$ations: ,e increased the reaction by a 1actor o1 2( 81ter the in"redients *ere added to recover the acid and the alcohol layer *e reali3ed that the layers *ere mi2ed !'( B(>mL o1 HCl *as added to the alcohol layer so to ma&e the sol!tion ne!tral$ JmL o1 deioni3ed *ater and =mL o1 B%H sodi!m carbonate *ere added( ,e !sed litm!s stri's to chec& the acidity o1 the sol!tion to ma&e s!re it *as ne!trali3ed( The acid layer had BmL o1 deioni3ed *ater and BmL o1 B%H sodi!m carbonate added so *e sim'ly added B(>mL o1 HCl be1ore the 'rod!ct *as 1iltrated o!t o1 the

sol!tion( The 'rod!ct o1 the alcohol layer *as a '!r'lish color *hen e2tracted yieldin" '!r'lish crystals the 1ollo*in" *ee& *hen *ei"ht and meltin" 'oint *ere meas!red( Results: Prod!ct '4chloroben3yl alcohol Prod!ct Kata 1or 8lcohol Layer Theoretical 8ct!al H +ield 8ct!al +ield +ield m(' %(2LJ" %(%J" CBH 6L46J Theoretical m(' =%4=2 H error C(>H

Prod!ct

'4chloroben3oic acid Calculations: H +ield 8lcohol Layer

Prod!ct Kata 1or 8cid Layer Theoretical 8ct!al H +ield 8ct!al +ield +ield m(' %(B 6 %(2L>" " >BH B664B=2

Theoretical m(' B J4B>%

H error

BCH

B9 divide act!al yield in "rams by theoretical yield 71o!nd in r2n analysis section9 in "rams 8cid Layer B9 divide act!al yield in "rams by theoretical yield 71o!nd in r2n analysis section9 in "rams H Error 8lcohol Layer B9 Ta&e an avera"e o1 both the theoretical and act!al meltin" 'oint ran"es 8ct!al E 76L ? 6J9/2 E 6L(>oC Theoretical E 7=% ? =29/2 E =BoC 7%(B 6 " / %(2L>"9 2 B%% E "&' reco$ered 7%(%J" / %(2LJ"9 2 B%% E %&' reco$ered

29 S!btract the theoretical val!e 1rom the act!al val!e and divide the ans*er by the theoretical yield$ then m!lti'ly by B%% 8cid Layer B9 Ta&e an avera"e o1 both the theoretical and act!al meltin" 'oint ran"es 8ct!al E 7B66 ? B=29/2 E B6JoC M76L(> G =B9/=B9N 2 B%% E %."' error

Theoretical E 7B J ? B>%9/2 E B J(>oC

29 S!btract the theoretical val!e 1rom the act!al val!e and divide the ans*er by the theoretical yield$ then m!lti'ly by B%% M7B6J G B J(>9/B J(>9N 2 B%% E &%' error

(iscussion)Conclusion: The '4chloroben3yl alcohol 1rom the alcohol layer *as '!re *ith a BoC meltin" 'oint ran"e and a C(>H error$ ho*ever only CBH o1 the 'rod!ct *as retrieved( S!ch a lo* H yield co!ld have been ca!sed by the acid and the e2tra in"redients *e added to ne!trali3e the sol!tion a1ter mista&in" the t*o di11erent layers( The crystals sho!ld have been a *hite color ho*ever o!rs ended !' bein" lavenderO this s!r'risin"ly did not a11ect the '!rity o1 this 'rod!ct( The res!lts 1o!nd *ith the '4chloroben3oic acid 1rom the acid layer ho*ever did not sho* s!ch 'romisin" res!lts( The meltin" 'oint ran"e *as 6oC and the H error *as BC$ this indicates that the 'rod!ct *as not '!re and somethin" *ent *ron" in the e2'eriment( 8"ain$ this and the >BH 'rod!ct retrieved may be e2'lained by the mi2 !' o1 the t*o di11erent layers( *iterature Article: #a"ai +$ Mat!bayasi #$ and #a&ahara M( -Hot ,ater 6nd!ces an 8cid4Cataly3ed Feaction in 6ts Pndissociated Iorm.( htt'://***(csQ(Q'/Qo!rnals/bcsQ/inde2(html ( Se'tember 2J$ 2%%C(