SIC2019

LAB REPORT EXPERIMENT 1: SYNTHESIS OF N-BUTYL PHENYL

ETHER VIA SN2 REACTION

PREPARED FOR: DR CHENG SIT FOON

NAME SUMAYYAH BINTI LOKMAN

MATRIC NO. 22003285/1

SESSION 2023/2024

SEMESTER 1

OCCURANCE 2

DATE OF 18th OCTOBER 2023

EXPERIMENT
Title:

Synthesis Of N-Butyl Phenyl Ether Via Sn2 Reaction

Introduction

SN2 reaction is a one step reaction involving nucleophile and electrophile (concerted

mechanism). The polarised C-X bond in haloalkanes leaves a partially positive carbon and a

partially negative halogen. An electrophile is an electron poor species that can accept a pair

of electrons. For instance, an electrophilic carbon would be one that is bonded to a halogen

in a haloalkane. An electron-rich substance with the ability to give two electrons is called a

nucleophile. A reaction which electrophiles and nucleophiles can react is called nucleophilic

substitution reaction. A group or atom known as the leaving group is displaced as a result of

an electron-rich nucleophile bonding with or attacking an electron-poor electrophile in

nucleophilic substitution processes. In this case, the leaving group is the halide.

The two processes that describe nucleophilic substitution of haloalkanes are as follows. A

negatively charged nucleophile attacks a haloalkane's electrophilic carbon in the first step.

The leaving group, the halogen of the haloalkane, leaves in the event of an attack. An anion

and a neutral R-Nu species are the end products. A neutral nucleophile targets a haloalkane's

electrophilic carbon in the second step. However, a positively charged product and an anion

are the end products of this attack. As the reaction is concerted, the steric effect causes the

nucleophile to attack from the back, opposite from the leaving group.

Objective:

1) To synthesis n-butyl phenyl ether via Sn2 reaction using absolute ethanol and sodium

metal.

2) To determine the boiling point of synthesised compound

Procedure

1. 0.044L of absolute ethanol and 3-4 boiling chips is added into two-necked round

bottomed flask.

2. 1.9g of sodium metal is cut and added into the reaction flask to react with ethanol

and observe the changes.

3. The round bottomed flask is put in the water bath to ensure the ethanol reflux slowly.

4. 7.8g of phenol is added in the same reaction flask after the reaction between ethanol

and sodium is complete and mixed thoroughly.

5. N-butyl bromide is dropped slowly into the reaction flask via dropping funnel within

one minute and the mixture is refluxed in water bath for 15 minutes.

6. Distillation apparatus is set up to distil excess ethanol in the mixture.

7. Reaction mixture is cooled down and 0.020 L of water is added.

8. The mixture is transferred into separating funnel.

9. The organic layer is washed with 10% Sodium Hydroxide solution, followed by 10%

sulfuric acid solution and water. The washing is done two times and using 0.005 L of

the solutions each time.

10. The organic layer is transferred into a dry conical flask and anhydrous magnesium

sulfate is added to absorb moisture from the organic layer.

11. The organic layer is filter into a pear-shaped flask using cotton.

12. The organic layer is distilled using air bath method.

13. The boiling point and weight of n-butyl phenyl ether obtained is recorded.
Reaction scheme:

Results and calculations

Reactant Mass(g) Molecular weight Number of mol

(g/mol)

n-butyl bromide
16.59 137.02 0.1211

Phenol
7.90 94.11 0.0839

Sodium
1.94 22.99 0.0844

n-butyl phenyl
2.83 150.22 0.0188
ether

Table 1: Information about reactant involved in reactions

 Calculation mass n-butyl bromide:

Volume of n-butyl bromide used= 13mL

Density of n-butyl bromide= 1.276g/mL

Mass of n − butyl bromide = 1.276 g/mL × 13mL = 16.59 g

Calculation of limiting reagent

Reactant Volume Density Molar mass Mass (g) Number of

(mL) (g/mL) (g/mol) mol

Ethanol
44.00 0.789 46.07 34.72 0.7536

n-butyl
13.00 1.276 137.02 16.59 0.1211
bromide

phenol
7.38 1.071 94.11 7.90 0.0839

Sodium
- - 22.99 1.94 0.0844

Table 2: Calculation of limiting reagent

In this reaction, 0.7536mol of ethanol are used to react with 0.0844mol of sodium

producing 0.0844mol of sodium ethoxide. Sodium is the limiting reagent.

In second reaction, 0.0844 mol of sodium ethoxide react with 0.0839 mol of phenol to

produce 0.0839 mol of sodium phenoxide. Phenol is the limiting reagent.

In the third reaction, 0.1211 mol of n-butyl bromide reacts with 0.0839 mol of sodium

phenoxide to produce 0.0839 mol of n-butyl phenyl ether. Sodium phenoxide is the

limiting reagent.

Theoretical yield of n-butyl phenyl ether

According to the calculation above, we can find the theoretical yield for n-butyl phenyl

ether.

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

So, 0.0839 mol sodium= 0.0839 mol n-butyl phenyl ether

𝑚𝑎𝑠𝑠 𝑛 − 𝑏𝑢𝑡𝑦𝑙 𝑝ℎ𝑒𝑛𝑦𝑙 𝑒𝑡ℎ𝑒𝑟 = 𝑛𝑢𝑚𝑏𝑒𝑟 𝑜𝑓 𝑚𝑜𝑙 × 𝑚𝑜𝑙𝑎𝑟 𝑚𝑎𝑠𝑠

𝑚𝑎𝑠𝑠 𝑛 − 𝑏𝑢𝑡𝑦𝑙 𝑝ℎ𝑒𝑛𝑦𝑙 𝑒𝑡ℎ𝑒𝑟 = 0.0839𝑚𝑜𝑙 × 150.22 𝑔/𝑚𝑜𝑙

𝑚𝑎𝑠𝑠 𝑛 − 𝑏𝑢𝑡𝑦𝑙 𝑝ℎ𝑒𝑛𝑦𝑙 𝑒𝑡ℎ𝑒𝑟 = 12.60𝑔

 Parameter Mass (g)

Empty pear-shaped flask

22.74

Pear-shaped flask+ synthesised compound

26.18

Synthesised compound
3.44

Table 3: Mass of n-butyl phenyl (synthesised compound) before air bath distillation

Parameter Mass (g)

Empty pear-shaped flask

29.27

Pear-shaped flask+ synthesised compound

32.10

Synthesised compound
2.83

Table 4: Mass of n-butyl phenyl (synthesised compound) after air bath distillation

Parameter Result

Volume of n-butyl phenyl ether

3.0 mL

Boiling point
190℃
 Boiling point range
(189℃-190℃)

Density of n-butyl phenyl ether

0.943 g/mL

Table 5: Information of n-butyl phenyl after air bath distillation

Parameter Theoretical Experimental

Boiling point
210℃ 190℃

Density
0.935 g/mL 0.943 g/mL

Colour
Clear colourless to pale Colourless

yellow

Table 6: Comparison theoretical vs experimental result of n-butyl phenyl ether

𝐴𝑐𝑡𝑢𝑎𝑙 𝑦𝑖𝑒𝑙𝑑 2.83𝑔

× 100% = × 100% = 22.46%
𝑇ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑 12.60𝑔
Discussion

In this experiment, n-butyl bromide (substrate) undergo nucleophilic substitution

reaction with phenoxide ion to produce n-butyl phenyl ether. Bromide ion acts as a leaving

group and replaced by phenoxide ion which attack from the back side.

The function of dropping funnel is to add n-butyl bromide slowly in order to prevent

quick addition resulting in side reaction or to prevent the reaction being too vigorous. The

temperature of the water bath should not exceed 100℃ as the boiling point of ethanol is

78℃. When the distillation is set up, the water flow from bottom to top as it will fill the

condenser fully. The water flowing downhill only fills the lowest part of the condenser with

the circulating water due to the restriction of gravity, which causes the gas passing through

the inner tube to cool less effectively. The distillation process is to remove excess ethanol

from the compound and the function of water flow through the condenser is to cool down

the ethanol and ensure that they condense to be collected in liquid form. Low actual yield

of n-butyl phenyl ether compared to theoretical yield may be caused by the incomplete

removal of ethanol in distillation step.

Function of separating funnel is to separate organic and aqueous layer in the

compound. The organic layer will float on top and the density of aqueous layer is greater

so it will appear on the bottom. Swirling the separating funnel will accumulate pressure in

the funnel so it needs to be released after a few moments swirling. It is not recommended

to shake the funnel strongly. Instead, swirl it gently to avoid emulsion formation.

The boiling point of n-butyl phenyl ether observed during air bath distillation is 190℃

which differ from the theoretical boiling point which is 210℃. This may be caused by the

impurities in the synthesised compound decrease the boiling point of n-butyl phenyl ether

obtained.
Suggestion for improvement

1. During distillation, make sure the thermometer is placed right between the junction so

that the boiling point is measured correctly.

2. The water level in water bath should be above the level of solution in the round bottom

flask so that the heat is evenly distributed.

3. The sodium should be pat dry using filter paper to remove paraffin oil before put into

reaction flask to reduce the time for reaction to occur.

4. Transfer the organic layer in the separating funnel from the top to prevent mixing

between aqueous layer residue left at the bottom of the flask.

Precaution step

1. Avoid inhaling absolute ethanol and phenol as they are corrosive to respiratory

tract.

2. Avoid sodium contact with water as it will react vigorously. Make sure the apparatus

that will be used are dry.

3. Avoid shaking the separating funnel too strongly to prevent formation of emulsion.

4. Handle phenol with care and avoid contact with skin as it is highly corrosive.

Conclusion

The synthesis of n-butyl phenyl through SN2 reaction is a success. The end product

obtained is a colourless solution with a range of 189℃-190℃ boiling point, 0.943g/mL

density and 22.46% percentage yield.

Reference

Dropping_funnel. (n.d.).

https://www.chemeurope.com/en/encyclopedia/Dropping_funnel.html

L. (2020, August 13). 5.2C: Step-by-Step Procedures. Chemistry LibreTexts.

https://chem.libretexts.org/Courses/SUNY_Oneonta/Chem_221%3A_Organic_Ch

emistry_I_(Bennett)/2%3ALab_Textbook_(Nichols)/05%3A_Distillation/5.02%3

A_Simple_Distillation/5.2C%3A_Step-by-Step_Procedures

L. (2023, January 23). SN2. Chemistry LibreTexts.

https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modul

es_(Organic_Chemistry)/Reactions/Substitution_Reactions/SN2

Organic Chemistry: Sn2E2 Reactions: The Sn2 Reaction | SparkNotes. (n.d.). SparkNotes.

https://www.sparknotes.com/chemistry/organic4/sn2e2/section1/#:~:text=Molecular%

20Orbital%20Explanation%20of%20SN2&text=The%20steric%20argument%20state

s%20that,makes%20front%20side%20attack%20impossible.

Post lab questions

1. Provide the reason for distilling excess ethanol from the reaction mixture after the reflux

process.

The reason to distil excess ethanol from the mixture is to ensure the end product which is

n-butyl phenyl ether is pure. Excess ethanol that is not distilled out from the mixture will
become the impurities for the end product and cause the characteristic of n-butyl phenyl

to deviate from the theory.

2. Provide the expected product when (R)-2-bromobutane reacts with phenoxide ion via

SN2 reaction. Show the stereochemistry clearly by drawing the structure of the starting

material and product.