LABORATORT REPORT OF INTRODUCTION TO ORGANIC CHEMISTRY

(CHM 413)

EXPERIMENT 8: PREPARATION OF CYCLOHEXENE FROM CYCLOHEXANOL

NAME : 1) NOOR SYAZA AQILAH BINTI AMRAN (2019317049)

: 2) AINNUR SYAMIRA BINTI KAMARUDIN (2019391257)

: 3) FATIN NADIAH BINTI SAYPOL ANWAR (2019704597)

: 4) NOR SYAFINI BINTI ROSLAN (2019717577)

GROUP : AS2462A1

LECTURER’S NAME : DR SUHAIDI ARIFFIN

DATE OF EXPERIMENT : 22TH OCTOBER 2019

DATE OF SUBMISSION : 5TH NOVEMBER 2019

 RESULTS

Boiling point 89.5 °C

Volume of product 11.5 mL

Colour change The addition of potassium permanganate solution, KMnO4 forms a dark brown
when tested with precipitate that indicates the presence of double bond of alkene from the product.
KMnO4 (aq) Cyclohexene is formed.

Dehydation of
cyclohexanol

Overall equation

3 + 2MnO4- + 4H2O
3

Cyclohexene Vincinal (diol)

+ 2MnO2 + 2OH-
 Distillation process

Figure 1 shows before addition of KMnO4 Figure 2 shows after addition of KMnO4
QUESTIONS

1. Find the moles of cyclohexane formed in the experiment. (2 marks)

Mass
Density =
Volume

Mass of cyclohexene = Density cyclohexene x Volume cyclohexene

g
= 0.811 x 11.5 mL
mL

= 9.3265 g

Mass cyclohexene
No of moles of cyclohexene =
Molar mass cyclohexene

9.3265 g
=
[6(12.01) + 10(1.008) g/mol

9.3265 g
=
82.14 g/mol

= 𝟎. 𝟏𝟏𝟑𝟓 𝐦𝐨𝐥

2. Calculate the expected mass of pure product cyclohexene using the number of moles
cylohexanol used in the experiment based on the equation. (2 marks)

Equation: C6H11OH(aq) → C6H10(aq) + H2O(l)

Mass of cyclohexanol = Density cyclohexanol x Volume cyclohexanol

g
= 0.962 x 20.0 mL
mL

= 19.24 g

Mass cyclohexene
No of moles of cyclohexanol =
Molar mass cycloehexene

19.24 g
=
[6(12.01) + 12(1.008) + 16.0 g/mol
 19.24 g
=
100.156 g/mol

= 𝟎. 𝟏𝟗𝟐𝟏 𝐦𝐨𝐥

From equation, 1 mol of cyclohexanol produce 1 mol of cyclohexene. So, 0.1922 mol of
cyclohexanol produce 0.1922 mol of cyclohexene.

𝐄𝐱𝐩𝐞𝐜𝐭𝐞𝐝 𝐦𝐚𝐬𝐬 𝐨𝐟 𝐜𝐲𝐜𝐥𝐨𝐡𝐞𝐱𝐞𝐧𝐞

= No of moles of cyclohexene x Molar mass of cycloehexene

= 0.1921 mol x 82.14 g/mol

= 𝟏𝟓. 𝟕𝟖 𝐠 𝐨𝐟 𝐜𝐲𝐜𝐥𝐨𝐡𝐞𝐱𝐞𝐧𝐞

3. Show the calculation for the percentage yield/conversion of cyclohexanol to cyclohexene.

Mass of cyclohexene = Density of cyclohexene x Volume of cyclohexene

g
= 0.811 x 11.5 mL
mL

= 9.3265 g

Actual yield
Percentage yield = x 100%
Theoretical yield

9.3265 g
= x 100%
15.78 g

= 𝟓𝟗%