Colour by Design - Arenes

13 important questions on Colour by Design - Arenes

What does benzene look like? Is it saturated or unsaturated?

A colourless liquid - very unsaturated

What is the molecular formula of benzene? What can be said about its shape and bond angles?

C6H6 

A flat hexagonal structure (planar) 

120 degrees

Why is the old structure of benzene (with three double bonds) no longer seen as correct?

- benzene does not undergo electrophilic addition reactions

- x-ray diffraction measurements show that the c-c bond lengths are equal (greater length than a double bond but less than a single bond)

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What makes benzene so stable?

The cyclic delocalisation of electrons - electrons repel each other, so a system in which they are delocalised and as far apart from one another as possible will involve minimum repulsion = stabilised

 

(this arrangement is much more stable than an alternate single/double bond arrangement) 

What does the stability of the benzene ring mean in the type of reactions it undergoes? 

It tends to undergo reactions in which the stable ring is preserved - reactions which disrupt the delocalisied electron system are less favourable and need higher temps and more vigorous conditions = it undergoes substitution reactions

What chemical test could be used to distinguish between 1,3,5-trimethylbenzene and phenylethene?

Shake with bromine water = 1,3,5-trimethylbenzene stays orange but phenylethene turns colourless.

Does benzene decolourise bromine solution?

nooooooo

What is a phenyl group? What is the molecular formula of phenyl?

 

A benzene ring in which one hydrogen atom has been substituted by another group.

C6H5

How many electrons are delocalisied in (a) benzene and (b) naphthalene? 

(a) 6

(b) 10

Why can't a molecule containing arene rings not easily be hydrogenated? 

All the double bonds are present in the arene rings and so will not be able to react easily. (pp june 2010 Q5(c))

Name two types of commercially important material whose manufacture involves the nitration of benzene.

- Dyes

- Explosives

How does a halogen carrier (e.g. AlCl3) allow the reaction between benzene and chlorine to take place?

It can form a dipole with the chlorine gas to form Cl+

Compare the different reactivities of benzene and alkenes towards chlorine. 

In benzene the electrons are delocalised/ spread out. In alkenes electrons are concentrated between two carbons - electrophiles are attracted more to greater electron density in alkenes.

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