102 ‫ أكثر من‬: ‫المستوى‬ ‫ كيمياء‬: ‫القسم‬ ‫ عبدهللا صابر السوداني‬: ‫االسم‬

Chapter III
Terpenoids

I- Complete the following sentences:

1- Terpenoids can be defined as the hydrocarbons of plant origin, whose structure is based on isoprene unit, as
well as their oxygenated, hydrogenated and dehydrogenated derivatives.”

2- The linkages of terpenoids units can be:

(1) Head to tail which can be drawn as or

(2) Tail to tail which can be drawn as

3- Terpenes are classified according to the number of isoprene units or number of carbon atoms

4- Essential oils are composed of two classes which are monoterpenes and sesquiterpenes, and an example for

this class is farnesol which structure can be drawn as

5- Tetraterpenes are considered as provitamin A because they are oxidized in the liver at the central double-bond
to yield vitamin A.

6- The IUPAC name of the isoprene unit is 2-methylbutan and its structure can be drawn as

7- The linkages of isoprene units in essential oils are head to tail which can be drawn as

8- The linkages of isoprene units in squalene are head to tail and tail to tail connection in the center.

9- An example of Sesquiterpenes is farnesol whose structure can be drawn as and

the linkage of isoprene units is head to tail

10- Farnesol belongs to Sesquiterpenes and its structure can be drawn as

11- Vitamin A is considered as Diterpenes and contains mono cycle

12- Tetraterpenes contains 40 carbon atoms

13- An example of acyclic Triterpene is squalene

14- One isomer of citral is neral and its structure can be drawn as while the other isomer is geranial

and its structure can be drawn as

15- Citral is a mixture of neral which is the cis-form and geranial which is the trans-form.

II- Put (√) or (X) on front of the following sentences:

1. The linkages of isoprene units in squalene are head to tail ( ×)

2. Vitamin A is a monocyclic diterpene (√)

3. B-Carotene is a tetraterpene considered as pro-vitamin A (√ )

4. Citral is considered as an essential oil (√ )

5. Tetraterpenes are composed of four isoprene units (× )

6. The isopropyl part in isoprene unit is called tail (× )

III- Write the structures of the following:

1- Menthol with numbering

6 2

4 3

2- Farnesol
 3- Vitamin A (mention to its class and sub-class)

Class: Diterpenes subclass: monocyclic

4- Neral

5- Squalene (mention to its class and sub-class)

Class: Triterpenes subclass: acyclic

IV- Give one example (with the structure and name) for each of the following:

1- Monoterpene

Ex: citral ( acyclic monoterpene )

 There are two isomers of citral

Neral (cis-citral) geranial (trans-citral)

2- Sesqiterpene

Ex: farnesol

3- Diterpene

Ex: vitamin A (Retinol)

4- Triterpene

Ex: squalene
 5- Essential oil

Monoterpenes + Sesquiterpenes + citral + menthol + farnesol

Citral menthol farnesol

V- Write about:

1. Classification of terpenes with suitable examples; illustrating the type of isoprene linkages in each class

A rational classification of the terpenes has been established based upon the number of isoprene (or or
number of carbon atoms) units incorporated in the basic molecular skeleton.

they are classified into 6 classes :

1. Monoterpenes

 They consist of 2 isoprene units (10 carbon atoms)

 The linkage of isoprene units is head to tail
 They are one of the components of essential oils

Ex: citral acyclic monoterpenes

Ex: menthol monocyclic monoterpenes

2. Sesquiterpenes

 They consist of 3 isoprene units (15 carbon atoms)

 The linkage of isoprene units is head to tail
 They are one of the components of essential oils

(Monoterpenes and Sesquiterpenes called essential oils)

Ex: farnesol acyclic Sesquiterpenes

3. Diterpenes

 They consist of 4 isoprene units (20 carbon atoms)

 The linkage of isoprene units is head to tail

Ex: vitamin A (retinol) monocyclic Diterpenes

 4. Triterpenes

 They consist of 6 isoprene units (30 carbon atoms)

 The linkage of isoprene units is head to tail except the central bond is tail to tail

Ex: squalene acyclic Triterpenes

5. Tetraterpenes / carotenoides

 They consist of 8 isoprene units (40 carbon atoms)

 The linkage of isoprene units is head to tail except the central bond is tail to tail

Ex: Beta-Carotene " provitamin A "

6. Polyterpenes

 They consist of more than 100 isoprene units (more than 5000 carbon atoms)

2. Sesquiterpenes with examples.

 They consist of 3 isoprene units (15 carbon atoms)

 The linkage of isoprene units is head to tail
 They are one of the components of essential oils
 Their structure can be acyclic , mono , bi or tricyclic

(Monoterpenes and Sesquiterpenes called essential oils)

Ex: farnesol acyclic Sesquiterpenes

VI- What are the major types of linkages of isoprene units in terpenoids? Give suitable examples

There are two major types of isoprene units

1. Head to tail linkage

2. Tail to tail linkage

 mono-, sesqui- and di-terpenes, the isoprene units are linked in a head to tail linkage
 Triterpenes and carotenoides are linked by head to tail except the central bond is tail to tail linkage
 Triterpenes and carotenoids contain one tail to tail connection in the center.