Answers:
Reaction Mechanism: a step by step account of all the electrons and bond changes in a chemical
reaction.
Nucleophile: a species that shares a pair of electrons with another atom to form a new covalent
bond; Lewis base
Electrophile: A species that gains a pair of electrons from another atom to form a new covalent
bond; a lewis acid
Curved Arrows: indicate flow of electrons
Brosted Base: Proton acceptor (i.e HO- aka: hydroxide ion)
Basic Concepts:
Mechanisms:
In Chemistry, one of the most important topics is mechanisms. Mechanisms are when two
compounds react with each other to form new and different products. Within Mechanisms, the
movement of electrons is shown which is quite important since every reaction involves the flow
of electron density (electrons are needed to break or form new bonds). To map out the flow of
electrons curved arrows are used.
Curved Arrows:
These curved arrows indicate how the reaction took place by representing the flow of an electron
pair.
Remember that even though these arrows look a lot like the arrows used in resonance, they are
not the same!!!
In resonance, the resonance structures do not exist because they are continuously altering
from one to another.
In mechanisms, however, the curved arrows actually show the movement of electrons.
Each arrow has a tail and a head. The tail is the location of the electrons and the head is where
they are going. In other words, it shows the electrons coming from the electron rich area to the
electron poor area.
TAIL
Electron Source:
where electrons are
coming from
HEAD
Electron
Destination:
where
electrons are
being moved
Also take note of the changes in formal charge on the oxygen and
carbon atom
Called A bromide
atom (-ide shows (-)
charge)
3. Bond bond
In this process there are usually two arrows which show the flow of electrons. First
the blue arrow shows the electrons from the pi bond forming a bond with the
hydrogen atom. Then since the hydrogen atom cannot have two bonds, the green
arrow shows the electrons going from the bond between hydrogen and chlorine
solely to the chlorine atom.
There can also be mechanisms that have two of the above steps:
Practice Problems
In each of the following molecules, classify the arrows shown as one of the three types
described above. (bondbond OR bondlone pair OR lone pair bond)
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1.
4.
Answers:
4.
Electron rich
On the Blunt end of arrow
Lewis base: electron pair donator
o Stronger base=stronger nucleophile
Will usually have pi bonds or lone pairs so that it can form a bond with
electrophiles
Practice Problems:
Part 1: Classify each compound as Nucleophile or Electrophile.
1.
2.
..
..
.
3.
4.
..
5.
Part 2:
Determine which Compound is the Nucleophile and which is
the Electrophile.
2.
1.
4.
3.
Answers:
Part 1:
1.Nucleophile
2.Nucleophile
3.Electrophile
4.Nucleophile
5. Electrophile
Part 2:
1.
3.
Part 3:
2.
4.
Works Cited
Klein, David R. Organic Chemistry as a Second Language. Danvers: John Wiley, 2004.
Print.
Hardinger, Steven. Chemistry 14C Lecture Supplement. 9th ed. Plymouth: Hayden-McNeil,
2011. Print
Hardinger, Steven. Chemistry 14C Thinkbook. 6th ed. Plymouth: Hayden-McNeil, 2008.
Print.
Google images for many images included in the tutorial