Chemistry Examination

Structured Questions
Top University Class

Imanuel Rava
21 August 2020

Q.1. Ionones
Ionones are a series of closely related chemical substances that are part of a group of
compounds known as rose ketones, which also includes damascones and damascenones.
Ionones are aroma compounds found in a variety of essential oils, including rose oil. -Ionone
is a significant contributor to the aroma of roses, despite its relatively low concentration, and
is an important fragrance chemical used in perfumery. The ionones are derived from the
degradation of carotenoids. Several other structure of Ionones is provided below,

Figure 1. The Ionones

Rank the acidity of the color coded hydrogen atoms in all the ionone isomers from the most
acidic to the least acidic, justify your answer as well. [25]

Q.2. Perfumery and Essential Oils

Essential oils are complex mixtures of volatile compounds produced by aromatic plants. They
are an immense source of organic chemical feed-stocks available and renewable. Since the
middle ages, they have been employed for their antiseptic and medicinal properties, including
antimicrobial, analgesic, sedative and antiinflammatory activities.
Farnesol is a molecule that makes flowers smell good (lilacs, for instance). Conversion of
farnesol into bisabolene and cadinene (the compound of the essential oils of junipers and
cedars) can be achieved by reacting it with hot concentrated sulphuric acid.

Figure 2. Compounds that is commonly founded in essential oils

a. Draw an appropriate arrow pushing mechanism for the transformation of farnesol into
bisabolene when reacted with hot concentrated H2 SO4. [5]

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Wardaya College – Department of Chemistry Chemistry Exam – Top University

b. Draw the minor product from the reaction between Farnesol and hot concentrated H2 SO4.
(Hint : The isomers of Bisabolene) [5]
Further conversion from bisabolene into cadinene is possible via 1,5-hydrogen shift. The figure
below show the proposed mechanism for the transformation of bisabolene to cadinene.

Figure 3. Proposed mechanism for the transformation of Bisabolene to Cadinene

c. Draw an appropriate arrow pushing mechanism for each step in the transformation of
bisabolene to cadinene. [7]

d. Explain the carbocation rearrangement in step 1, why it favors the secondary carbocation
compared to the tertiary carbocation. [3]

e. In step 3, we observe there is a large migration of carbocation intermediate. Explain how

the carbocation can migrate that far. [5]

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