R3.

4 Electron-pair sharing reactions

Table of contents

Electron-pair sharing reactions

Written specifically for students to provide help and support for the IB Diploma chemistry
programme this page provides full coverage of the syllabus content of Topic R3.4 Electron-
pair sharing reactions. It encourages you to think critically and provides many questions
with fully worked answers so that you can monitor and improve your knowledge and
understanding.

Guiding Question

What happens when reactants share their electron pairs with others?

Learning outcomes

After studying this topic you should be able to:

Understand:

a nucleophile is a
reactant that forms a
bond to its reaction
partner (the electrophile)
by donating both bonding
electrons.
in a nucleophilic
substitution reaction, a
nucleophile donates an
electron pair to form a
new bond, as another
bond breaks producing a
leaving group.
heterolytic fission is the
breakage of a covalent bond when both bonding electrons remain with one of the two fragments formed.
an electrophile is a reactant that forms a bond to its reaction partner (the nucleophile) by accepting both
bonding electrons from that reaction partner.
alkenes are susceptible to electrophilic attack because of the high electron density of the carbon-carbon
double bond. These reactions lead to electrophilic addition.
Apply your knowledge to:

recognize nucleophiles in chemical reactions.

deduce equations with description and explanation of the movement of electron pairs in nucleophilic
substitution reactions.
explain with equations, the formation of ions by heterolytic fission.
recognize electrophiles in chemical reactions.
deduce equations for the reactions of alkenes with water, halogens, and hydrogen halides.

Consider links to other topics

What is the difference between the bond breaking that forms a radical and the bond breaking that occurs in
nucleophilic substitution reactions?

Why is bromine water decolourised in the dark by alkenes but not by alkanes?

Why are alkenes sometimes known as “starting molecules” in industry?

Relationships & vocabulary

Nature of Science

Organic chemical reactions involving functional group interconversions (e.g. substitution and addition reactions)
are among the key factors responsible for the progress made in the development and applications of scientific
research.
International-mindedness

For examples and more links of Incorporating IB chemistry into a real world context see Putting Topic R3 -
Electron and electron-pair sharing reactions - into context (3).
Vocabulary

nucleophile nucleophilic "curly arrow" substrate

substitution

electrophile electrophilic leaving groups

addition

Flashcards

Show flashcards
Learning slides

You can use this slide gallery for learning or for reviewing concepts and information. It covers all the key points in
the syllabus for this sub-topic.
‹›

Something to think about

Because they undergo nucleophilic substitution reactions it is often stated:

“Halogenoalkanes are more reactive than alkanes.”

A rather nice Nature of Science exercise might be to question the validity of this statement. Is it a valid statement
that is always true?

It is certainly true that alkanes undergo very few different types of chemical reactions. This is mainly due to the
relative strengths of the C−H and C−C bonds, and the fact that carbon cannot expand its octet. Contrast this with
many halogenoalkanes where the carbon atom bonded to the halogen atom is electropositive and can undergo
substitution reactions with nucleophiles such as the hydroxide ion, the cyanide ion or ammonia. The statement
clearly does have some validity. However it is certainly not always the case. One of the hazards associated with
aircraft and other vehicles that use alkanes as a fuel is that if there is a fuel leak due to an accident then there is
a very real danger of fire. All alkanes are very reactive when it comes to burning them in oxygen. Compare this
with halogenoalkanes, in particular fluorocarbons. Fluorine is a highly electronegative element which will make
the carbon atom attached to it very electropositive so fluorocarbons would be expected to react readily with
nucleophiles. In fact they are completely inert. This is due to the very strong C−F bond. The irony is that certain
halogenoalkanes (e.g. bromochlorodifluoromethane, known as halon 1211) are so unreactive that they are
carried in aircraft to combat alkane fires – in this instance alkanes are very definitely much more reactive than
halogenoalkanes.

When it comes to combustion,

halon1211 (left), a
halogenoalkane, is much less
reactive than methane (right), an
alkane.

Another good example to show

that in many cases
halogenoalkanes are actually less
reactive than alkanes is to
compare the polymers
poly(tetrafluoroethene), PTFE,
and poly(ethene). PTFE, which is
also known as Teflon®, is the 'non-stick' polymer which is so inert that it is used to coat cooking utensils.
According to Plastech the only chemicals known to affect Teflon® finishes are certain alkali metals and some of
the most highly reactive fluorinating agents such as xenon difluoride and cobalt(III) fluoride. Compared to this
poly(ethene) is much more reactive.

Test your understanding of this topic

Practice questions available to you immediately:

You have direct access to ten multiple choice practice questions with the answers explained see: Practice
questions: R3.4 Electron-pair sharing reactions.

Possible restricted access questions:

(Note that your teacher may have restricted your access to some or all of these questions and worked answers if
they are going to use them as a class test or set them as an assignment.)
For ten 'quiz' multiple choice questions with the answers explained see MC Test: R3.4 Electron-pair sharing
reactions.

For short-answer questions see R3.4 Electron-pair sharing reactions questions.

Other resources

1.

OUP Study Guide (Neuss): Pages 133, 134

2. One of the problems with videos about nucleophilic substitution is that many of them also go into the SN1 and
SN2 mechanisms which are not on the SL part of the syllabus. This one, by Master Organic Chemistry, just
covers the basics of what a nucleophilic substitution reaction is.

Introduction to Nucleophilic Subst…

Subst…

Nucleophilic substitution

3. In some countries the use of bromine water is prohibited. If this is the case you may need to see a video
although, of course, it is much better if you can perform the experiment for yourself.
Testing for unsaturated hydrocarb…
hydrocarb…

Test for unsaturation