SIC2002

ORGANIC CHEMISTRY II

NAME : SITI NURSYAFIQAH BINTI AHMAD BASARUDIN

MATRIC NO : SIC180033
PROGRAM : BACHELOR IN SCIENCE OF CHEMISTRY
EXPERIMENT : 1
TITLE : SN2 REACTION PREPARATION OF n-BUTYL PHENYL ETHER
LECTURER : DR.NOORDINI BINTI MOHAMAD SALLEH
DATE : 13 NOVEMBER 2019
CLASS : S
TITLE : SN2 REACTION PREPARATION OF n-BUTYL PHENYL ETHER
OBJECTIVE :
1) To determine the boiling point and weight of n-Butyl phenyl ether.
2) To determine the weight and percentage of yield of n-Butyl phenyl ether.
EXPERIMENTAL:

1) Reaction scheme
 2) Calculating of limiting reagent :

Reactant Mass (g) Molecular weight Mole

(g/mole)
n-butyl bromide 16.51 137.02 0.1205
Phenol 7.89 94.11 0.0829
Sodium 1.9374 22.99 0.0129
n-butyl phenyl 150.22
ether
𝑚𝑎𝑠𝑠 𝑜𝑓 𝑟𝑒𝑎𝑐𝑡𝑎𝑛𝑡
Number of mole of reactants :
𝑚𝑜𝑙𝑎𝑟 𝑚𝑎𝑠𝑠 𝑜𝑓 𝑟𝑒𝑎𝑐𝑡𝑎𝑛𝑡

Mole of n-butyl bromide: mole of phenol: mole of sodium: mole of ethanol:

16.51𝑔 7.8𝑔 1.9374𝑔 34.716𝑔
= = = =
137.02𝑔/𝑚𝑜𝑙 94.11𝑔/𝑚𝑜𝑙 150.22𝑔/𝑚𝑜𝑙 46.07𝑔/𝑚𝑜𝑙

= 0.1205 mol = 0.0829 mol = 0.0129 mol = 0.7535mol

From the chemical equation above :

1 mol of sodium = 1 mol of ethanol

1 mol of sodium = 1 mol of sodium ethoxide
1 mol of sodium ethoxide = 1 mol of phenol
1 mol of phenol = 1 mol of sodium phenoxide
1 mole n-butyl bromide = 1 mole sodium phenoxide
1 mol sodium phenoxide = 1 mol n-Butyl phenyl ether

1 mol of phenol = 1 mol n-butyl bromide

0.0829 mol of phenol = 0.0829 mol n-butyl bromide

∴ the limiting reactant is phenol

1 mol of phenol = 1 mol n-butyl phenyl ether

0.0829 mol of n-butyl bromide = 0.0829 mol n-butyl phenyl ether

Theoretical yield of n-butyl phenyl ether

=0.0829 mol x 150.22 g/mol
=12.4532g
RESULT:
1) Mass of a n-butyl phenyl ether (crude product) before air bath distillation.

Parameter Unit (g)

Mass of pear-shaped flask 18.1058
Mass of pear-shaped flask + n-butyl phenyl ether (crude product) 23.2764
Mass of n-butyl phenyl ether (crude product) 5.1706

2) Mass of n-butyl phenyl ether after air bath distillation:

Parameter Unit (g)

Mass of pear-shaped flask 34.1128
Mass of pear-shaped flask + n-butyl phenyl ether 38.9369
Mass of n-butyl phenyl ether 4.8241

Boiling point of n-butyl phenyl ether : 208oC

Volume of n-butyl phenyl ether:
𝑚𝑎𝑠𝑠 𝑜𝑓 𝑛−𝑏𝑢𝑡𝑦𝑙 𝑝ℎ𝑒𝑛𝑦𝑙 𝑒𝑡ℎ𝑒𝑟
Density =
𝑣𝑜𝑙𝑢𝑚𝑒 𝑜𝑓 𝑛−𝑏𝑢𝑡𝑦𝑙 𝑝ℎ𝑒𝑛𝑦𝑙 𝑒𝑡ℎ𝑒𝑟
5.3465𝑔
0.935 g/ml = 𝑣𝑜𝑙𝑢𝑚𝑒 𝑜𝑓 𝑛−𝑏𝑢𝑡𝑦𝑙 𝑝ℎ𝑒𝑛𝑦𝑙 𝑒𝑡ℎ𝑒𝑟

Volume of n-butyl phenyl ether = 5.7182 ml

Percentage of yield for n-butyl phenyl ether:

𝑒𝑥𝑝𝑒𝑟𝑖𝑚𝑒𝑛𝑡𝑎𝑙 𝑦𝑖𝑒𝑙𝑑 𝑜𝑓 𝑛−𝑏𝑢𝑡𝑦𝑙 𝑝ℎ𝑒𝑛𝑦𝑙 𝑒𝑡ℎ𝑒𝑟
= x 100%
𝑡ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑 𝑜𝑓 𝑛−𝑏𝑢𝑡𝑦𝑙 𝑝ℎ𝑒𝑛𝑦𝑙 𝑒𝑡ℎ𝑒𝑟
4.8241
= x 100%
12.4523

= 38.74%
Percentage of purity of n-butyl phenyl ether
𝑚𝑎𝑠𝑠 𝑜𝑓 𝑛−𝑏𝑢𝑡𝑦𝑙 𝑝ℎ𝑒𝑛𝑦𝑙 𝑒𝑡ℎ𝑒𝑟
= 𝑚𝑎𝑠𝑠 𝑜𝑓 𝑛−𝑏𝑢𝑢𝑡𝑦𝑙 𝑝ℎ𝑒𝑛𝑦𝑙 𝑒𝑡ℎ𝑒𝑟 (𝑐𝑟𝑢𝑑𝑒 𝑝𝑟𝑜𝑑𝑢𝑐𝑡) x 100%
4.8241
= 5.1706 x 100%

=93.30%
DISCUSSION
Reaction mechanism:
SN2 mechanism

For this experiment, the mechanism involve is SN2 mechanism. This is because the
alkyl halide that we use is primary alkyl halide which is n-butyl bromide and it is not bulky.
The phenoxide is a nucleophile that will attack n-butyl bromide forming the intermediate
form before producing the n-butyl phenyl ether as a product. The bromide will become the
leaving group in this reaction.

SUGGESTION FOR IMPROVEMENT :

For improvement, take ethanol after taking the sodium metal because the process to
cut the sodium metal take a time and ethanol might evaporate or cover the reaction flask
that contain ethanol with cotton wool to avoid this happened. The sodium metal must be
dissolves in ethanol. Do not shake strongly as a lot of emulsion may be form while wash the
organic layer with NaOH, H2SO4 and water.

PRECAUTION STEP :
1) Make sure that sodium metal did not contact with water.
2) Make sure that sodium metal did not contact with our skin when handling it
because it may cause burn on human skin
3) Make sure that wear the glove while conducting the experiment because we use
the chemical that might be dangerous for the skin.
4) Make sure to check the condenser either there is a leaking or not before set up the
apparatus.
5) Make sure that the apparatus was dry before use it.

CONCLUSION :
1) The percentage of yield for n-butyl phenyl ether is determined which is 38.74%.
2) The boiling point for n-butyl phenyl ether is 208oC.
POST-LAB QUESTION:
1) Why must the excess alcohol be separated?
Excess alcohol must be separated because it would be affected the formation of n-
butyl phenyl ether. It is because it will slow the reaction because of the hydrogen
bonding

2) If (R)-2-bromobutane reacted with phenoxide ion through SN2 reaction, what will
be the expected product. State the stereochemistry of the compound. Draw the
structure of the compound with the correct stereochemistry)
The product produce is (S)-sec-butylphenyl ether.