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Helps with line drawings and different types of isomers as well for in-depth, Lecture notes of Chemistry

Covers line drawings and how to draw bonds

Typology: Lecture notes

2022/2023

Uploaded on 12/17/2023

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H
C
C
C
C
H
HH
H
C
H
H
H
C
H
H
H
H
1
The larger a molecule is, the more complex its VSEPR diagram.
Complex structures take time to draw!
2. Line diagrams also focus on important structural details.
An example; the difference in the hydrocarbon backbone of the
geometrical isomers E-3-methyl-2-pentene and
Z-3-methyl-2-pentene
Let’s convert the line drawing of E-3-methyl-2-pentene to a VSEPR:
Carbon atoms are assumed to be located at the end of each bond, which may be a
line or “set” of lines.
Stable carbon atoms are always assumed to have four bonding interactions.
Notice a double bond represents two bonding interactions
What do you think a triple bond represents?
These missing bonds to carbons
are assumed to be to H, so H’s
are added.
H+H
H
+
+
1. When examining chemical reactivity
eliminating structural details not relevant to the
chemistry or simplifying VSEPR diagrams to
line diagrams reduces complexity.
Z-3-methyl-2-pentene
E-3-methyl-2-pentene
The 3D nature is
completed by changing
bonds to wedges and
hatches where needed.
Compare your completed diagrams
to the model geometries given in
VSEPR to see if they are correct
H
C
C
C
C
H
HH
H
C
H
H
H
C
H
H
H
H
pf3
pf4

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H

C

C

C

C

H

H H

H

C

H

HH

C

H

HH

H

The larger a molecule is, the more complex its VSEPR diagram.Complex structures take time to draw!

Line diagrams also focus on important structural details.

An example; the difference in the hydrocarbon backbone of thegeometrical isomers E-3-methyl-2-pentene andZ-3-methyl-2-pentene

Let’s convert the line drawing of E-3-methyl-2-pentene to a VSEPR:

Carbon atoms are assumed to be located at the end of each bond, which may be a

line or “set” of lines. •^

Stable carbon atoms are always assumed to have four bonding interactions.

•^

Notice a double bond represents two bonding interactions^ What do you think a triple bond represents?

•^

These missing bonds to carbons

are assumed to be to H, so H’sare added.

H

+^

H

H

1. When examining chemical reactivityeliminating structural details not relevant to thechemistry or

simplifying VSEPR diagrams to

line diagrams reduces complexity

Z-3-methyl-2-pentene

E-3-methyl-2-pentene

The 3D nature iscompleted by changingbonds to wedges andhatches where needed.

Compare your completed diagramsto the model geometries given inVSEPR to see if they are correct

H

C

C

C

C

H

H H

H

C

H

HH

C

H

HH

H

Remember this involves putting back into the diagram ALL missing elements.

Carbon atoms are inserted at the ends of bonds

UNLESS there is already an atom there. •

Stable carbon atoms are always assumed to have

four bonding interactions, any missing bonds must beinserted, and those bonds are to H atoms.

multiple bonds count as more than one bonding

interaction ie a double bond is two, a triple bond is three.

Bonds between “hetero”atoms (atoms other than C

and H) and other atoms (H, O etc…) are “expanded”. •

Any missing lone pairs are added.

Let’s convert a line diagram that possesses more than just C/H to a VSEPR diagram

V. Mozol 2023

H^2

N

C C

O

O H^2

N

C C

O

O

H H

H

N 2

O

O

H N

C C

O

O

H

H H

H N

C C

O

O

H

H H

V. Mozol 2023

For any molecule you should be able to see the relationshipbetween line drawings, condensed molecular formula, Lewisdiagrams, or VSEPR diagrams.

e.g. D-glucose

Condensed Stereochemical information is lost, what is thatstereochemical information?

“best” Lewis How does thisdiagram differ fromthe drawing given bybiologists to the rightof the page?REMEMBER that forchemists Lewisdiagrams have NO 3Dinformation.

Partial VSEPR and Line Drawings Chemists use VSEPR, and subsequently line diagrams to understand Stereochemistry and the approach ofmolecules for reaction.Can you see where there can be stereoisomerism in D-glucose?

OHCH

(CH(OH))

CHO

or

OHCH

(CH(OH))

C(O)H

C O

C

H

H O

H C O

C

O C H

C O

H

H

H

H

H

O

H

H H

Caution must be taken Biologists use Fischer Projections toclassify Carbohydrates. They looklike Lewis diagrams BUT theserepresentations have 3D informationembedded in them. This informationis for VERY non-stable conformers. InChem 201 we want you to drawenergetically stable conformations,Fischer Projections were invented in1891 BEFORE the structures forcarbohydrates were OBSERVED.This is amazing!!!!!!!.

when evaluating the

molecular

representations

presented in other

courses.