Honors Chemistry II

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PREPARATION OF TERT-BUTYL CHLORIDE FRO TERT-BUTYL ALCOHOL

P!r"ose# To synthesi$e %-&h'oro-%-methy'"ro"ane (tert-)!ty' &h'oride* +rom %methy'"ro"an-%-o' (tert-)!ty' a'&oho'*, Dis&!ssion# The s!)stit!tion o+ a hydro-y' .ro!" /ith a ha'ide +o''o/s the 0N1 me&hanism,
Cl H OH H HCl

1*

%*

H C
+

H2O

2*

Cl

Cl

(1* Protonation o+ the hydro-y' .ro!" &reates an e-&e''ent 'ea3in. .ro!" 4 a /ater mo'e&!'e, (%* The /ater 'ea3es5 &reatin. a &ar)o&ation5 (2* /hi&h then )onds /ith the &h'oride ion to +orm the "rod!&t, The +o''o/in. e6!i"ment set!" dia.rams /i'' )e !sed thro!.ho!t the "ro&ed!re, Re+er to these as needed, Fi.!re 1# 0e"aratory F!nne' Fi.!re %# 7ra3ity Fi'tration Fi'ter "a"er 0e" +!nne' Iron rin. 89 mL Bea:er Rin. stand Rin. stand 89 mL Bea:er 7'ass +!nne'

Fi.!re 2# 0im"'e Disti''ation

!ermometer wit! adapter

3-way adapter

Water out Condenser

"a#uum distilling adapter

50 mL round bottom flask Water in Heating mantle 50 mL beaker

O);e&ti3es# In this 'a)5 yo! /i'',,, 1, synthesi$e %-&h'oro-%-methy'"ro"ane +rom %-methy'"ro"an-%-o', %, 3eri+y the identity o+ yo!r "rod!&t )y determinin. its )oi'in. "oint, 2, &a'&!'ate the "er&ent yie'd o+ %-&h'oro-%-methy'"ro"ane, 0a+ety# <ear sa+ety .o..'es at a'' times /hi'e in the 'a), 0ome &h'orinated hydro&ar)ons ha3e )een :no/n to )e &ar&ino.eni&, Do not to!&h any o+ the &hemi&a's /ith yo!r hands, <ash yo!r hands +re6!ent'y and re"ort any s"i'' immediate'y, Fi'ter Pa"er (1%,8 &m* Rin. 0tand 0ma'' Iron Rin. 0im"'e Disti''ation 0et!" Boi'in. Chi"s I&e 1%,1 HC' tert-)!ty' A'&oho' Disti''ed <ater 1 NaHCO2 Anhydro!s Na%0O=

ateria's# 89 mL Bea:er =99 mL Bea:er 1%8 mL 0e"aratory F!nne' 19 mL 7rad!ated Cy'inder 1%8 mL Er'enmeyer F'as: Fi'ter F!nne' Pro&ed!re#

1, In the +!me hood5 "o!r 29 mL o+ &on&entrated HC' into a 89 mL )ea:er, %, Coo' the &on&entrated HC' to 8>C in an i&e )ath (=99 mL 1?2 +!'' o+ i&e and ta" /ater*, 2, Po!r the &oo'ed HC' into a 1%8 mL se"aratory +!nne' (see Fi.!re 1*, =, Add 19,99 mL o+ tert-)!ty' a'&oho' and .ent'y sha:e the mi-t!re, A''o/ the mi-t!re to stand +or %9 min!tes,

8, O&&asiona''y d!rin. the %9 min!te "eriod (e3ery 2 min!tes or so*5 .ent'y sha:e the mi-t!re, A+ter sha:in.5 in3ert the se" +!nne' and o"en the sto"&o&: to re'ie3e "ress!re, @, A+ter %9 min!tes5 a''o/ the mi-t!re to stand !ndist!r)ed !nti' the 'ayers ha3e se"arated, P'a&e the 89 mL )ea:er !nder the sto"&o&: on the se" +!nne' and drain the )ottom a6!eo!s 'ayer into the )ea:er (see Fi.!re 1*, C'ose the sto"&o&:, A, Add 8 mL o+ disti''ed /ater to the se" +!nne', 7ent'y sha:e5 a''o/ to stand and se"arate5 then drain the /ater 'ayer into the )ea:er, B, Re"eat ste" A /ith 1 NaHCO25 then a.ain /ith 8 mL o+ disti''ed /ater, C, Trans+er the "rod!&t to a 1%8 mL Er'enmeyer +'as: and add a""ro-imate'y % . o+ anhydro!s Na%0O=, This is &a''ed Ddryin.E the "rod!&t, 19, 7ra3ity +i'ter the DdriedE tert-)!ty' &h'oride "rod!&t (see Fi.!re %*, Re&ord the 3o'!me o+ tert-)!ty' &h'oride o)tained, 11, Determine the )oi'in. "oint o+ the "rod!&t to 3eri+y its identity !sin. a sim"'e disti''ation set!" (see Fi.!re 2*, This /i'' "re3ent any o"en e3a"oration o+ tert-)!ty' &h'oride, The a&&e"ted )oi'in. "oint +or tert-)!ty' &h'oride is 89,C>C, 1%, Ca'&!'ate the F yie'd o+ tert-)!ty' &h'oride,

C'ean!"# D!m" a6!eo!s so'!tions do/n the drain /ith "'enty o+ r!nnin. /ater, P'a&e t-)!ty' &h'oride in the or.ani& /aste &ontainer, C'ean a'' .'ass/are thoro!.h'y, - Rinse +irst /ith a&etone5 then soa"5 then disti''ed /ater,