FACULTY OF APPLIED SCIENCES

LABORATORY REPORT

FUNDAMENTAL ORGANIC CHEMISTRY

(CHM 457)
Title of Experiment Preparation of 1-bromobutane
from 1-butanol
No. Experiment 3
Name of Student Norhidayu bt Adnan
Student ID Number 2021898286
Programme Code AS2532A
Date of Experiment is Done 14/04/2022
Date of Lab Report is Submitted 21/04/2022
Lecturer’s Name Dr Najmah bt P.S. Hassan
Title: Preparation of 1-bromobutane from 1-butanol
Objectives:
i) To prepare 1-bromobutane from 1-butanol
ii) To determine the percentage yield of the product

Chemicals and Apparatus

i. List all the chemicals used
- 17.0 g sodium bromide
- 17 mL water
- 10.0 mL n-butyl alcohol
- 14 mL concentrated H2 SO4
- 14 mL 9 M H2 SO4
- 14 mL H2 O
- 14 mL saturated aqueous sodium bicarbonate
- 1.0 g anhydrous calcium chloride

ii. Draw the reaction apparatus setup for the reaction

Results and Discussion

i. State the function of sulphuric acid in the experiment?

The sulphuric acid is used as a catalyst to remove water from 1-butanol.

ii. What will happen if the sulfuric acid is added rapidly and the temperature of the
solution is high?
To avoid high amount of hydrobromic acid that might oxidise into bromine gas.
iii. Explain why the upper layer, after refluxed contained the product 1-bromobutane
and the layer switched at the point where water is used to extract the organic layer.
It is because the 1-bromobutane is denser than water.

iv. How to identify that the layer is organic?

To identify the layer is organic is when water is added and mixed with 1-
bromobutane in the separatory funnel, it will form 2 layers which are aqueous layer
and organic layer. The organic layer will be the lower layer because density of 1-
bromobutane is higher than water.

v. Calculate the percentage yield of 1-bromobutane if the actual yield obtained is

6.8992 g. (refer to the manual for the amount reagents used).

Molecular weight of 1-butanol = 74.1 g/mol

0.81 𝑔 1 𝑚𝑜𝑙
𝑚𝑜𝑙1−𝑏𝑢𝑡𝑎𝑛𝑜𝑙 = 10.0 𝑚𝐿 × ×
1 𝑚𝐿 74.1 𝑔
= 0.1093 𝑚𝑜𝑙

1 mol of 1-butanol produced 1 mol of 1-bromobutane

∴ 0.1093 𝑚𝑜𝑙 of 1-butanol produced 0.1093 mol of 1-bromobutane

Molecular weight of 1-bromobutane = 137.02 g/mol

Theoretical weight of 1-bromobutane = 0.1093 𝑚𝑜𝑙 × 137.02 𝑔/𝑚𝑜𝑙

= 14.98 𝑔

6.8992 𝑔
∴ 𝑃𝑒𝑟𝑐𝑒𝑛𝑡𝑎𝑔𝑒 𝑦𝑖𝑒𝑙𝑑 = × 100%
14.98 𝑔
= 46.06 %

vi. In the video, 11 mL of propanol was used. How much (in mL) of butanol would
be needed to prepare 1-bromobutane if all the other reagents are remained the
same.

In the video, the mole of butanol used is 0.15 mol

74.1 𝑔
Mass of butanol = 0.15 𝑚𝑜𝑙 × 1 𝑚𝑜𝑙

= 11.12 𝑔
 1 𝑚𝐿
Volume of butanol = 11.12 𝑔 × 0.81 𝑔

= 13.73 mL

vii. Show the step-by-step of reactions mechanism on the formation of 1-bromobutane

from 1-butanol.

Conclusion

In conclusion, the experiment was successful because 1-bromobutane was synthesised

from 1 butanol and the product's % yield was calculated. The theoretical mass of 1-
bromobutane is 14.98 g, but the experimental mass is 6.8992 g, according to the findings.
The percentage yield of the experiment calculated is 46.06 %.
References

i. Libretexts, & Clark, J. (2020, September 13). Dehydrating Alcoholc to Make

Alkenes. Chemistry LibreTexts. Retrieved from
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modul
es_(Organic_Chemistry)/Alcohols/Reactivity_of_Alcohols/Dehydrating_Alcohols
_to_Make_Alkenes

ii. Watson, S. (n.d.). Experiment 7 Preparation of 1-Bromobutane. Organic Chemistry

Resources. Retrieved from
http://myweb.liu.edu/~swatson/downloads/files/Experiment_7.pdf

Questions:

Aqueous sodium bicarbonate was used to wash the crude n-butyl bromide. What is the purpose
of this wash?
To neutralise any remaining unreacted bromide in crude n-butyl bromide.