SEMINAR 2: ORGANIC CHEMISTRY Farah Mohamed Rasidi

Answer all questions. (Date of discussion: 10 November 2017)

Group Exercise:

1. The diagram below shows the skeletal formula of β-carotene, which is an orangey
yellow pigment found in carrots and leafy green vegetables. Many people take β-
carotene as a dietary supplement because there is some evidence that high levels of β-
carotene are associated with low incidences of cancer.

a) Explain briefly why β-carotene is coloured.

- β-carotene is orange coloured due to the long-conjugated chain of altering double bonds of
the beta-carotene molecular structure.
- The conjugated chain in carotenoids allows the absorption of green and blue part of the
visible light spectrum, leaving red and yellow colours from the spectrum to be reflected back
to the viewer.
- Hence, the combination of red and yellow light reflected will cause the beta-carotene to
appear orange colour.

b) What is the functional group present in β-carotene?

- β-carotene is composed of two retinyl groups

c) What is the molecular formula and empirical formula of β-carotene?

- Molecular formula: C40H56
- Empirical formula: C5H7

d) Explain what will happen when a few drops of β-carotene are shaken separately with
distilled water and benzene.
-When a few drops of β-carotene are shaken with distilled water, a two-layered mixture is
formed because β-carotene is non-polar thus it is immiscible in water
-When a few drops of β-carotene are shaken with benzene, a homogenous mixture is formed
because β-carotene is non-polar soluble in organic compound benzene

e) Predict and explain what will happen when a small amount of β-carotene is

i. added to bromine and shaken.

-Bromine added into β-carotene turns from brown to colourless as β-carotene
undergoes electrophilic addition with bromine molecules.
-As β-carotene contains 11 double bonds, these 11 double bonds have high
electron densities thus they are susceptible to electrophilic attack.
-11 bromine molecules are then polarized by 11 double bonds and the bromine
atom in each bromine molecule that is closer to a double bond is partially
 positively charged, hence partial positively charged bromine atom will act as
an electrophile to attack the double bond, binding bromine atom to a carbon
atom with a (C-Br) bond and forming a carbocation intermediate that is
electron deficient.
-Positive bromide ion formed will then act as a nucleophile that attacks the
carbocation intermediate, binding itself to the electron deficient carbon atom
with a (C-Br) bond. As this goes on for the other 10 bromine molecules, all 22
bromine atoms will bind to one β-carotene molecule.
–Hence, the bromine molecules will eventually turn from brown to colourless.

ii. refluxed with acidified potassium manganite (VII). –Acidified potassium

manganite (VII) will turn from purple to colourless because β-carotene will
undergo oxidation under reflux with acidified potassium manganite (VII), in
which purple MnO4- ions are reduced to colourless Mn2+ ions.