EX?

ERIMENT

HYDROI'YSIS A KINETIC STUDY IN TIIE UNIMOLECULAR OF /-BUTYL CHLORIDE

Objectives
understand more about In the end of rhis exPeriment, students should

. .

The basis of nucleophilic substitution rcaction' through experimenting on various The mechanism of a reaction can be studied solvent and temPerature .eaction conditions such as concentration of reactant'

Introduction

ln the previous experimenl, we have inveslrgated the nLlclenphiliu 'ubstilutronstudy rhe In rhis experioent, you \oill i.""iril* r,^ria" ion and alcohol as a substrlte.alkyl halide (substrate) in a hydrolysis (nucleophile) and a rertiary ;;;;;".i;"*
process.

reacli^n

(CH3)rCCl +

HrO -- >

(CIITLCOII + IICI
at room-tempeftture-

In aqueous solution, t-butyl chloride is easily hydrolysed hydrol\sis process rrr" _."hun'ia- of reaction can be determined by measuring the ln doing so' under sevetal conditions of concentrations and tempetature the "ran,l,",l""fu *".tion -i*t*" need to be withdnwn at specified intenals sincebase il"-rl','p"t" so lhe remarning

quantity of-base' reaction is conducted in the presence of a knorvn the ,r Drrticular time will give information as to the ertenl of the re3ction Ho\\'e\'er' hecon'e ^ of reacranr\ u Plocess as the concentrations

"i,i"

;;ff;;;;;.;; r;;. il;.;

an rncomplele stage as e3rly as it quickly' progr.sses to oUtain the useful information much more

'i.?-.on"unting rcaction can be cGed out the ';

in

the use of colour In ihis experiment, a reaction extent of l0 7o is employed and progess- The indicalor' indicator will sirnplify the observation of lhe reaction il."."pi"r"i ur"" iJ blue in colour in the mixture of r-butyl chloride' sodium hydroxide' of hydrochloric acid (reaction by acetone and water will tum yellow in the presence *tti.n indicated all the base has been consumed The time when indicator 06 of reaction is complete ".oau",, changei its color indicatcd l0

'E]{perimental Outcome
temperature upon the mechanism of To study the effects of concentration of reactant and hydrolysis of rbutYl chloride.

Chemicals

't4-\ M
aqueous sodium hydroxide and

0.1

aqueous r-butyl chlodde in;acetone, 0.1 brcmpheiol blue indicator. J

Apparatus
25

ml conical flask, 50

ri

water bath.

burette, stopwatch, 0-110.C thermometer, 1000 ml bake. and

Experimental Procedures

A.
L

Reaction 10 % Complete.

2.

experiment. Into a clean, dry 25 ml conical flask, dispense g S{,oi!J l4jSqgolqtbgtyt ch]9lirle-solution. P.!999.1Q:3_rnLgt-0.1 M aqueoui sodium nvarqii&, 6.i ,nl or distilled water and 3 drops of bromop-F-enolblue indiciio?-i-o iseparate 25rnl conical flask.

xour lab instructor will prepare 0.1 M aqueous r-butyl chloride in acetone and a idq-qoft .tr-onsTesE-soiu6oni cariT-dispensed fm a 50 m] burette. Take note on tie rcom temperature during the course of

The followjng reaction will happen so fast when the solutions are mixed. Start timing the rcaction with stopwatch or w.ist digital watch.

3.

4-

pour the entile mixture back into the fiIst flask to ensure adequate mixing of components. Note the time when the solution tums yellow. Repeat the process at least twice or when the ."iding. -. not more than 2_3 seconds apad. All recorded concentration and time values will be used to calculate the value ofthe aeaction rate, t based on the expression:

Place a piece of white papr under the both flasks. Observe the time to the nearest second and_quickly add t-butyl chloride solution into the flask containing aqueous sodium hydroxide mixture and start timing the stopwatch_ As quickly as poisible,

k=2.3 t -lo

in mol Llsecond

-1

1-

7o

reaction finish 100

r
B. Reaction 20 % Complete.

1/

Repeat the previous procedure but use double volumes of aqueous sodium hydrcxide (0.6 r ) and distilled waier (6.4 ml). Make sure you record the rime whel the solution tums to yellow accurate]y_

C. Chanee in Reactant Concentration-

l-

30 q)
en

e ple
ac,tone

in

tfqgq{gbut before mixing bol.h solutions, add l0 rnl of a Lrabtioito the flask containing lhe base. Record rhe-tme

.change of color of solution happens.

D. Change in Temperature.

l.

2.

Repeat part 1 at two other temperahEes. Your demon$trator will select the temperatures, which are 20 qC below and 10 'C above rcom temperafirxe. Clake note that this analysis is qualitative, unless a constant water bath is aviilable;. Thus, in case of low temperature, ice-water bath will be used ard apprcpdate steam oriot water bath is provided in the case of high temperaturc. Immerse both fla.sks cottaining unmixed reactants in the proper bath until desircd temperature is reached (take the temperature of the solution of base). Oncc the solution reached the desired temperaturc, mix the reactants while solution is kept in a bath until the reaction is complete (changes in colour). A piece of wire wound around the neck of the flasks and hooked over the edge of the beaker provides convenient suPport.

x 103, where T is the absolute temperature and is the late constant. Calculate the activation energy, E from the slope of the line. Note: Slope = EJ2-303R wherc R is a constant with rhe value 1-982 caloriedegre-Imol-r.
Plot

'log

versus

l/f

Questions

l.
2.

the concentration

On the basis of the experiment, explain whethcr the reaction rale is dependable on of sodium hydroxide?

Based on the experiment, does the reaction late depend on the concentratioD reactant?

of

3- By taking the overall

expe.imental results into accoult, discuss whethet solvolysis reaction of t-butyl chlodde undergoes by SNI or SN2 mechanisms?