Lab Report: Experiment 10.

Nucleophilic Substitution Reactions of Alkyl Hali es

Last Name (or Surname) (type): ___Budinskaya________________________ Signature (by Hand): ________________________________ First Name (or Given Name) (type): ___Anastasia________________________ Section (type): M __ !________ "ate Submitted (type): ___#$%##%$ #&_____________ 'A names (type): #) ________(a))avi________________________________________ $) _________Nisc*a)_______________________________________ !nstructions: +omp)ete t*e ,o))o-in. Lab /eport -it* your ans-ers and submit to your 'A durin. your )ab section ,or .radin.0 Late reports -i)) *ave si.ni,icant deductions (see course sy))abus)0 "1 N1' c*an.e t*e ,ormat o, t*e report (mar.ins2 order o, items2 keep scorin. on t*e ri.*t *and side etc0) (oints -i)) be deducted i, you a)ter t*is Lab /eport 'emp)ate0 3ou can *it 45nter6 to create more space ,or eac* 7uestion or section0 'ype your response ('imes Ne- /oman2 #$pt ,ont) -*ere indicated0 o For e8amp)e0 #0 9uestion: ANS;5/ #: type your ans-er *ere Fi)) in t*e b)ank<0$A<0 ANS;5/ $A: type your ans-er *ere 3ou may dra- structures by *and= a)) ot*er responses must be typed un)ess indicated ot*er-ise0 1t*er *and -ritten te8t -i)) not be .raded0

'*is Section is to be Fi))ed out by t*e 'A on)y: "ra er #ull Name: $$$$$$$$$$$$$$$$$

'ota) (oints: _______% >!

Experiment 10. Nucleophilic Substitution Reactions of Alkyl Hali es #0 %urpose: (____%& pt)

(3our ans-er s*ou)d inc)ude t*e types o, reactions you -i)) run and di,,erent parameters you -i)) study0)

ANS;5/ : !n this experiment& factors that influence the rate of SN' an SN1 reactions (ere analy)e & in particular ho( the rate of these reactions is influence by the structure of the alkyl hali e& nature of the lea*in+ +roup& an concentrations of reactants an soli s. ,he effect of the temperature (as e*aluate in irectly.

Results an

iscussion

$0 +reate t*e e8act 'ab)e # at t*e bottom o, pa.e ?? o, t*e )ab Manua)2 and ,o))o- t*e instruction on pa.e ?? and ,i)) in t*e 'ab)e0 (____%> pt) ANS;5/:

reactivity Na! in Acetone -SN'. #=bromobutane $=bromobutane $=bromo=$=met*y)propane bromobenCene rt 8 8 ye))o- 8 8 @ A+ no r8n time (s) $s ?min Bmin

A+N/0 in Ethanol -SN1. #=bromobutane $=bromobutane $=bromo=$=met*y)propane bromobenCene 8 8 8 8 @0@min # s $s

&0 ;rite do-n t*e product ,or eac* o, t*e reactions ,or t*e ,o))o-in. SN$ and SN# reactions0 See 'ab)e # o, pa.e B o, Lab Manua)0 (____%> pt) (3ou can *and dra- t*e products2 indicate i, t*ere is no reaction)

ANS;5/ :

SN' reactions entries:

NaD E Br+H$+H$+H$+H&

NaD E +H&+HBr+H$+H&

NaD E +H&+(+H&)Br+H$+H&

NaD E (*Br no reaction

"o t*e same ,or t*e rest o, t*e entries in 'ab)e # (pa.e B2 )ab manua))0

SN1 reactions entries:

A+N/0 E Br+H$+H$+H$+H&

A+N/0 E +H&+HBr+H$+H&

A+N/0 E +H&+(+H&)Br+H$+H&
3

A+N/0 E (*Br no reaction

>0 "iscuss t*e c*emica) reactivity o, a primary *a)ide ,or SN$ and SN# reactions2 and provide a reason ,or your c*emica) reactivity comparison bet-een SN$ and SN#0 ANS;5/ :

(_____%$ pt) (_____%$ pt)

(rimary a)ky) *a)ides react -it* t*e SN$ mec*anism becasue nuc)eop*i)ic attack is easy and not sterica))y *indered0 (rimary a)ky) *a)ides -ou)d ,orm a primary carbocation i, reacted in SN# -*ic* -ou)d be too unstab)e to proceed -it* a reaction0 So t*e SN$ reaction -it* a primary *a)ide is concerted and )ooks )ike t*is:

@0 "iscuss t*e c*emica) reactivity o, a tertiary *a)ide ,or SN$ and SN# reactions2 and provide a reason ,or your c*emica) reactivity comparison bet-een SN$ and SN#0

(_____%$ pt) (_____%$ pt)

ANS;5/ : SN$ substitution does not occur -it* tertiary a)ky) *a)ides because t*ey are too *indered ,or nuc)eop*i)ic attack0 SN# substitution occurs -it* tertiary a)ky) *a)ides because t*ey ,orm stab)e carbocations -*ic* can t*en be attacked ,rom eit*er side by a nuc)eop*i)e even -*en attack on t*e opposite side o, t*e )eavin. .roup is pre,erred0 B0 Sol*ent effect. For t*e reaction o, $=c*)orobutane and A.N1& in t-o so)vent systems2 et*ano) and @ F et*ano)%@ F -ater2 -*ic* so)vent system .ives a ,aster reaction: (_____%# pt)
4

ANS;5/ : So)vent t*at contained @ F et*ano) @ F -ater .ave t*e ,aster reaction0 Based on t*e so)vent e,,ect2 does t*e reaction proceed more as a SN$ or SN# reaction: (_____%# pt)

ANS;5/ : Based on t*e so)vent e,,ect2 t*e ,act t*at et*ano) is po)ar protic2 t*e reaction proceeds via SN#0 !0 1onclusion: (____%! pt)

"escribe resu)ts (SN$2 SN#2 primary2 secondary structure2 )eavin. .roup2 so)vent e,,ect) and -*at t*ey imp)y or mean0 '*is conc)usion may be )on.0 ANS;5/ : Dn conc)usion2 t*e SN$ and SN# reactions -ere -e)) s*o-n in di,,erent so)vents0 Dn 'ab)e #: it can be seen t*at t*e compounds t*at reacted at a *i.*er temperature (@ +) via an SN$ reaction in acetone2 reacted at room temperature -*en p)aced in et*ano) to react via an SN#mec*anism0 '*ese resu)ts can be attested to t*e primary and secondary structures respective)y re7uired to react in t*ese mec*anisms at room temperature0 '*e )eavin. .roup -ou)d b)ock t*e secondary structure to react in SN$ un)ess speci,ic so)vent e,,ect conditions -ere met suc* as i, t*e so)vent -as po)ar and aprotic and t*e nuc)eop*i)e -as a -eak base2 )ike cyanide ion or a)co*o)2 t*en SN$ substitution -ou)d be possib)e0

Appen ix: Exercise for conceptual un erstan in+. ?0 "iscuss t*e nature o, )eavin. .roups +)2 Br2 and D on t*e c*emica) reactivity ,or SN$ and SN# reactions2 and provide a reason ,or your rankin. o, t*e reactivity due to e,,ect o, t*ese )eavin. .roups on SN$ and SN#0 (_____%$ pt) ANS;5/ : An SN# reaction speeds up -it* a .ood )eavin. .roup because t*e )eavin. .roup is invo)ved in t*e rate=determinin. step0 A .ood )eavin. .roup -ants to )eave so it breaks t*e + bond ,aster0 1nce t*e bond breaks2 t*e carbocation is ,ormed and t*e ,aster t*e carbocation is ,ormed2 t*e ,aster t*e nuc)eop*i)e can come in and t*e ,aster t*e reaction -i)) be comp)eted0 An SN$ reaction ,o))o-s t*e same ru)es ,or )eavin. .roups2 t*ere is on)y one step t*ou.*2 makin. it t*e rate determinin. step0 +)2 Br2 and D are arran.ed ,rom -orst to best )eavin. .roups because as you .o ,rom )e,t to ri.*t on t*e periodic tab)e2 e)ectron donatin. abi)ity decreases and t*us abi)ity to be a .ood )eavin. .roup increases0

G0 Give t-o e8amp)es o, po)ar aprotic so)vents0 ANS;5/ :

(_____%# pt)

5t*y) acetate Acetone # 0 Give t-o e8amp)es o, po)ar protic so)vents0 ANS;5/ : 5t*ano)2 -ater ##0 Ds it )ike)y t*at a nonpo)ar protic so)vent e8ists: ANS;5/ : Not )ike)y2 un)ess in an e8treme case0 #$0 ;*ic* type o, so)vent is best ,or a SN$ reaction: ANS;5/ : po)ar aprotic #&0 ;*ic* type o, so)vent is best ,or a SN# reaction: ANS;5/ : po)ar protic (_____%# pt) (_____%# pt) (_____%# pt) (_____%# pt)

#>0 '*e product structure is incomp)ete ,or t*e ,o))o-in. SN$ reaction0 Fi)) it in so it is comp)ete -it* correct stereoc*emistry0 (_____%# pt) ANS;5/ #&:

#@0 '*e product structures are missin. ,or t*e ,o))o-in. SN# reaction0 Fi)) 'H5M in -it* s*o-in. t*e stereoc*emistry0 (_____%# pt)

%re2Lab:

(_______%# pts)

Be sure to *and in your carbon copy to your 'A be,ore you )eave )abH As t*at is -*at -i)) be .raded *ere0 /ead eac* e8perimenta) procedure care,u))y and ,o))o- t*e instructions ,or ,u)) credit0 For e8amp)e i, you are asked -*at your observations are =-rite t*em do-n (e0.0 -*ite so)id2 .as evo)ution observed Ibubb)esJ) and remember to keep track o, a)) units0 3ou -i)) be e8pected to ,i)) out your pre=)ab as described in detai) in t*e 1r.anic +*emistry Laboratory Manua) (pa.e !=# ) ,or t*is course0 5ac* -eek you -i)) submit t*e carbon copy o, your )ab to your 'A ,or .radin. and t*e end o, eac* )ab0 !f the carbon copy is not le+ible it (ill not be +ra e 34se your car boar i*i er bet(een pa+es.

#or this (eek: 4n er research plan& make sure you inclu e all balance chemical e5uations for SN1 an SN' reactions -primary& secon ary structure an lea*in+ +roup in*esti+ation. !f you think no reaction then (rite 6No reaction7
'*ere is not*in. you need to type in t*is section ,or credit= on)y carbon copies% dup)icates -i)) be )ooked at0