Alkenes and The Nature of Organic Reactions

Alkenes
• Hydrocarbons that contain a carbon-carbon double bond
• Occur abundantly in nature
• Many have important biological roles

Naming Alkenes

• Also known as unsaturated hydrocarbons

• Follows the same naming convention of alkanes, except for a few
parts:
• Ends in –ene, instead of –ane.
• Double bonds will always be a part of the parent chain
• Double bonds will take priority in giving the lowest carbon number
• If more than one double bond is present, use the prefixes di-, tri-, and so on.
• Cycloalkenes are named like cycloalkanes: double bonds will always be
between carbons 1 and 2 and the first substituent will always have the lowest
carbon number possible.
Cis-Trans Isomerism in Alkenes
• Single bonds allow free rotation of a carbon in its plane of axis.
• Double bonds do not allow free rotation; if you rotate a double bond,
the structure of the molecule itself must rotate.
• Has a chemical consequence

Cis-Trans Isomerism in Alkenes

Sequence Rule: E,Z Designation

• Cis-trans naming system works well for disubstituted alkenes, but not
for tri and tetrasubstituted double bonds.
• E,Z system of nomenclature: designates priorities to substituents on
the double bond carbons
• Rank the atoms directly attached to each carbon according to their
atomic number. The higher the atomic number, the higher the priority.
• Z isomer have high-priority substituents on the same side, but are on
the opposite side in the E isomer
Sequence Rule: E,Z Designation
• Cis-trans naming system works well for disubstituted alkenes, but not
for tri and tetrasubstituted double bonds.
• E,Z system of nomenclature: designates priorities to substituents on
the double bond carbons
• If a decision is not reached by ranking the first atoms in the
substituents, look at 2nd, 3rd or 4th atoms away from the double bond
until the first difference is
found.
• Ethyl will have higher priority than methyl because C has higher
atomic number than the H atoms in the methyl group.
• Multiple-bonded atoms are equivalent to the same number of single-
bonded atoms

Kinds of Organic Reaction

Organic reactions can be organized by either what or how chemical
reactions occur.
What Reactions
• Addition reaction: two reactants add together to form a single
product
A+B→C
• Elimination reaction: a reactant splits into two products
A→B+C

Kinds of Organic Reaction

Organic reactions can be organized by either what or how chemical
reactions occur. What Reactions
• Addition reaction: two reactants add together to form a single
product
A+B→C
• Elimination reaction: a reactant splits into two products
A→B+C
Kinds of Organic Reaction
How Reactions Occur
Reaction Mechanism: overall description of how a reaction occurs
• All chemical reactions involve bond breaking and bond formation.
• Bonds can break symmetrically (homolytic bond breaking)
A:B → A· + ·B
• Bonds can break unsymmetrically (heterolytic bond breaking)
A:B → A+ + :B-
Kinds of Organic Reaction
How Reactions Occur
Reaction Mechanism: overall description of how a reaction occurs
• All chemical reactions involve bond breaking and bond formation.
• Bonds can form symmetrically (homogenic bond formation)
A· + ·B → A:B
• Bonds can form unsymmetrically (heterogenic bond formation)
A + + :B-→ A:B
Kinds of Organic Reaction
How Reactions Occur
• Radical Reactions: processes that involve symmetrical bond breaking
and formation
• Radicals: chemical species that contain an odd number of valence
electron
• Polar Reactions: processes that involve unsymmetrical bond breaking
and formation
• Terms such nucleophile and electrophile are used
• Nucleophile is electron-rich (can donate a pair of electrons; usually
negatively charged)
• Electrophile is electron-poor (can accept an electron pair from
nucleophiles; usually
positively charged)