2.

1 Representing Molecules

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2-1 Klein, Organic Chemistry 1e
 2.2 Bond-line Structures
• The bond-line structure is easier to read and to draw:

vs.

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2-2 Klein, Organic Chemistry 1e
 2.2 Bond-line Structures
• Like Lewis structures, lines are drawn between atoms to show covalent bonds:

• Atoms are bonded at angles (zigzag) that represent the actual geometry of the
bond angles.
• Carbon atoms are not labeled, but a carbon is assumed to be located at every
corner or endpoint on the zigzag.

• If you are given a Lewis structure or condensed structure, you must also be
able to draw the corresponding bond-line structure:
– Represent the bond angles with zigzags:

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2-3 Klein, Organic Chemistry 1e
 2.2 Bond-line Structures
– Follow VSEPR and spread out the electron pairs on a central atom:

– Single bonds are axes of rotation, so be aware that they can rotate.

– Heteroatoms (atoms other than C and H) should be labeled with all

hydrogen atoms and lone pairs attached.
– NEVER draw a carbon with more than FOUR bonds!

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2-4 Klein, Organic Chemistry 1e
 2.3 Indentifying Functional Groups

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2-5 Klein, Organic Chemistry 1e
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2 -6 Klein, Organic Chemistry 1e
• Identify the functional group(s) present in the molecule
below:

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2 -7 Klein, Organic Chemistry 1e
 2.4 Bond-line Structures With
Formal Charge
• Most carbon atoms will have FOUR covalent bonds and no lone pairs to avoid
carrying a formal charge.
– Sometimes carbon will have a +1 charge. In such cases, the carbon will
only have THREE bonds.

– Sometimes carbon will have a -1 charge.

• If carbon carries a charge in a molecule, the charge MUST be shown on the

bond-line structure.
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2-8 Klein, Organic Chemistry 1e
 2.5 Bond-line Structures and Lone
Pair Electrons
• Sometimes lone pairs are omitted from bond-line
structures. For example:

– You can’t determine the formal charge on the N atom unless

you know how many electrons there are on the N.
– It could be:

• You must ALWAYS draw formal charges on a bond-line

structure to eliminate confusion.
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2-9 Klein, Organic Chemistry 1e
 2.6 3D Bond-line Structures
• The vast majority of molecules are 3-dimensional (3D), but it is difficult to
represent a 3D molecule on a 2-dimensional (2D) piece of paper or
blackboard.
• We will use dashed and solid wedges to show groups that point back into the
paper or out of the paper.
• Dashed and solid wedges to show groups that point back into the paper or
out of the paper.

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2-10 Klein, Organic Chemistry 1e
 2.6 3D Bond-line Structures
• Here are some other ways to show 3D structure:

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2-11 Klein, Organic Chemistry 1e
 2.7 Resonance
• If all of the carbons have unhybridized p
orbitals, they can overlap.

• All three overlapping p orbitals allow the

electrons to move throughout the overlapping
area simultaneously.

• That’s RESONANCE.
• From a molecular orbital point of view,
when the THREE unhybridized p
orbitals overlap, THREE new MOs are
formed.

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2-12 Klein, Organic Chemistry 1e
 2.7 Resonance
• Resonance makes a molecule MORE stable through:
– Delocalization of electrons:
• Electrons in resonance exist in orbitals that span a greater distance
giving the electrons more freedom.
– Delocalization of charge:
• The charge is spread out over more than one atom. The resulting
partial charges are more stable than a full +1 charge.

δ+ δ+
resonance hybrid

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2-13 Klein, Organic Chemistry 1e
 2.8 Curved Arrows in Resonance
• Rules for using curved arrows to show RESONANCE:
1. Avoid breaking a single bond.

– single bonds can break, but NOT in RESONANCE.

– Resonance occurs for electrons existing in overlapping p orbitals, while
electrons in single bonds are overlapping sp, sp2, or sp3 (sigma) orbitals.
2. Never exceed an octet for 2nd row elements (B, C, N, O, F)
– Atoms in the 2nd row can only have four 2nd energy level orbitals holding
a max. of 8 electrons.
– Examples of arrows that violate rule 2.

3. 2nd row elements (B, C, N, O, F) will rarely, but sometimes, have LESS
than an octet.

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2-14 Klein, Organic Chemistry 1e
 2.9 Formal Charge in Resonance
• When using curved arrows to show RESONANCE,
structures will often carry a formal charge that must be
shown.
• In the resonance, the arrows tell us how to move the
electrons to obtain the other contributor.

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2-15 Klein, Organic Chemistry 1e
 2.10 Patterns in Resonance
• There are 5 main bonding patterns in which resonance
occurs. Recognize these patterns to predict when
resonance will occur:
1. Allylic lone pairs
2. Allylic positive charge
3. Lone pair of electrons adjacent to a positive charge
4. A pi bond between two atoms with different
electronegativities
5. Conjugated pi bonds in a ring

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2-16 Klein, Organic Chemistry 1e
 2.10 Patterns in Resonance

• Summary – Figure 2.5:

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2-17 Klein, Organic Chemistry 1e
 2.10 Patterns in Resonance

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2-18 Klein, Organic Chemistry 1e
 2.11 Stability of Contributors
• How do we assess the stability of resonance contributors?
1. Formal charge generally DECREASES stability.
2. A +1 charge on an electronegative atom or -1 on a low electronegativity
atom is especially unstable.
3. COMPLETE OCTETS INCREASE stability.

• The octet rule is usually a bigger factor than formal charge when assessing
stability.
• For each structure, assess the stability of each contributor, and draw a
resonance hybrid.

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2-19 Klein, Organic Chemistry 1e
 2.12 Delocalized vs. Localized
• Localized electrons are NOT in resonance.
• Delocalized electrons ARE in resonance.
– Delocalization increases stability.
• There are a couple ways to recognize electrons that
are delocalized through resonance?
1. To be delocalized, electrons must exist in an UNHYBRIDIZED
p orbital that can overlap with p orbitals on neighboring
atoms.
2. To be delocalized, electrons must be on an sp or sp2
hybridized atom.

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2-20 Klein, Organic Chemistry 1e
 2.12 Delocalized vs. Localized
• The sp2 hybridization of
the nitrogen atom causes
it to be trigonal planar
rather than tetrahedral.

• To be delocalized, all
three atoms involved
MUST have p orbitals
overlapping.

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2-21 Klein, Organic Chemistry 1e
 2.12 Delocalized vs. Localized
• Generally, lone pars adjacent to a C=C double bond
are capable of resonance, but not in this case.

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2-22 Klein, Organic Chemistry 1e
 Exercise 1

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2 -23 Klein, Organic Chemistry 1e