arac&ve)forces:)boiling)and) …...... 36.1) c • hexane)))))68.7) c • heptane)))))98.4) c...

A"rac&ve Forces: Boiling and Mel&ng Points and Bicyclic System

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Page 1: Arac&ve)Forces:)Boiling)and) …...... 36.1) C • Hexane)))))68.7) C • Heptane)))))98.4) C • Octane)))))125.7) C induceddipoleinduceddipole)) interac&ons) van)der)Waals)forces)

A"rac&ve Forces: Boiling and Mel&ng Points and Bicyclic System

Page 2: Arac&ve)Forces:)Boiling)and) …...... 36.1) C • Hexane)))))68.7) C • Heptane)))))98.4) C • Octane)))))125.7) C induceddipoleinduceddipole)) interac&ons) van)der)Waals)forces)

Boiling Points

The greater the a"rac&ve forces between molecules, the higher the boiling point.

A"rac&ve forces

Boiling Points

• Methane 167.7 °C • Ethane –88.6 °C • Propane –42.1 °C • Butane –0.5 °C • Pentane 36.1 °C • Hexane 68.7 °C • Heptane 98.4 °C • Octane 125.7 °C

induced dipole-‐induced dipole interac&ons

van der Waals forces

The greater the surface area of the molecule,

the higher the boiling point.

Page 4: Arac&ve)Forces:)Boiling)and) …...... 36.1) C • Hexane)))))68.7) C • Heptane)))))98.4) C • Octane)))))125.7) C induceddipoleinduceddipole)) interac&ons) van)der)Waals)forces)

Branching Lowers the Boiling Point

“cigar” “tennis ball”

Page 5: Arac&ve)Forces:)Boiling)and) …...... 36.1) C • Hexane)))))68.7) C • Heptane)))))98.4) C • Octane)))))125.7) C induceddipoleinduceddipole)) interac&ons) van)der)Waals)forces)

Dipole–Dipole Interac&ons

Van der Waals Van der Waals dipole–dipole

Dipole–dipole interac&ons are stronger than van der Waals forces.

Page 6: Arac&ve)Forces:)Boiling)and) …...... 36.1) C • Hexane)))))68.7) C • Heptane)))))98.4) C • Octane)))))125.7) C induceddipoleinduceddipole)) interac&ons) van)der)Waals)forces)

Compara&ve Boiling Points

Page 7: Arac&ve)Forces:)Boiling)and) …...... 36.1) C • Hexane)))))68.7) C • Heptane)))))98.4) C • Octane)))))125.7) C induceddipoleinduceddipole)) interac&ons) van)der)Waals)forces)

Compara&ve Boiling Points

The larger the halogen, the more polarizable it is.

Page 8: Arac&ve)Forces:)Boiling)and) …...... 36.1) C • Hexane)))))68.7) C • Heptane)))))98.4) C • Octane)))))125.7) C induceddipoleinduceddipole)) interac&ons) van)der)Waals)forces)

Hydrogen Bonds in H2O and NH3

CH4 –167.7 °C H2O 100 °C no hydrogen bonds hydrogen bonds

Hydrogen bonds are stronger than other dipole–dipole interac&ons.

Page 9: Arac&ve)Forces:)Boiling)and) …...... 36.1) C • Hexane)))))68.7) C • Heptane)))))98.4) C • Octane)))))125.7) C induceddipoleinduceddipole)) interac&ons) van)der)Waals)forces)

Hydrogen Bonds in Water

Page 10: Arac&ve)Forces:)Boiling)and) …...... 36.1) C • Hexane)))))68.7) C • Heptane)))))98.4) C • Octane)))))125.7) C induceddipoleinduceddipole)) interac&ons) van)der)Waals)forces)

Hydrogen Bonds in Amines

Hydrogen bonds are stronger in primary amines than in secondary amines because primary amines have stronger dipole–dipole interac&ons.

Ter&ary amines cannot form hydrogen bonds with each other.

Page 11: Arac&ve)Forces:)Boiling)and) …...... 36.1) C • Hexane)))))68.7) C • Heptane)))))98.4) C • Octane)))))125.7) C induceddipoleinduceddipole)) interac&ons) van)der)Waals)forces)

Hydrogen Bonds in Proteins

Page 12: Arac&ve)Forces:)Boiling)and) …...... 36.1) C • Hexane)))))68.7) C • Heptane)))))98.4) C • Octane)))))125.7) C induceddipoleinduceddipole)) interac&ons) van)der)Waals)forces)

Compounds with Similar Shapes and Proper&es O]en Have Similar Physiological Ac&vi&es

Drugs bind to their receptors by van der Waals interac&ons, dipole-‐dipole interac&ons, and hydrogen bonding.

Page 13: Arac&ve)Forces:)Boiling)and) …...... 36.1) C • Hexane)))))68.7) C • Heptane)))))98.4) C • Octane)))))125.7) C induceddipoleinduceddipole)) interac&ons) van)der)Waals)forces)

Mel&ng Points

alkanes with an odd number of carbons pack less &ghtly. The mp is influenced by the packing of the molecules in the crystal la`ce

Page 14: Arac&ve)Forces:)Boiling)and) …...... 36.1) C • Hexane)))))68.7) C • Heptane)))))98.4) C • Octane)))))125.7) C induceddipoleinduceddipole)) interac&ons) van)der)Waals)forces)

Solubility

like dissolves like

Polar compounds dissolve in polar solvents (H2O).

Nonpolar compounds dissolve in nonpolar solvents (hexane).

Page 15: Arac&ve)Forces:)Boiling)and) …...... 36.1) C • Hexane)))))68.7) C • Heptane)))))98.4) C • Octane)))))125.7) C induceddipoleinduceddipole)) interac&ons) van)der)Waals)forces)

Solva&on

Solva&on is the interac&on between solute molecules and solvent molecules.

Page 16: Arac&ve)Forces:)Boiling)and) …...... 36.1) C • Hexane)))))68.7) C • Heptane)))))98.4) C • Octane)))))125.7) C induceddipoleinduceddipole)) interac&ons) van)der)Waals)forces)

An Oxygen Can Drag Three Carbons Into Water

Page 17: Arac&ve)Forces:)Boiling)and) …...... 36.1) C • Hexane)))))68.7) C • Heptane)))))98.4) C • Octane)))))125.7) C induceddipoleinduceddipole)) interac&ons) van)der)Waals)forces)

“Like Dissolves Like” is Important in Drug Ac&on

Crossing the blood–brain barrier requires a fat-‐soluble drug.

THC and barbiturates have a hydrocarbon tail to facilitate crossing the barrier.

Page 18: Arac&ve)Forces:)Boiling)and) …...... 36.1) C • Hexane)))))68.7) C • Heptane)))))98.4) C • Octane)))))125.7) C induceddipoleinduceddipole)) interac&ons) van)der)Waals)forces)

Solubili&es of Alkyl Halides

Page 19: Arac&ve)Forces:)Boiling)and) …...... 36.1) C • Hexane)))))68.7) C • Heptane)))))98.4) C • Octane)))))125.7) C induceddipoleinduceddipole)) interac&ons) van)der)Waals)forces)

• Boiling points and mel&ng points increase as size of alkane increases • Dispersion forces increase as molecule size increases, resul&ng in higher

mel&ng and boiling points

Physical Proper&es of Alkanes

Page 20: Arac&ve)Forces:)Boiling)and) …...... 36.1) C • Hexane)))))68.7) C • Heptane)))))98.4) C • Octane)))))125.7) C induceddipoleinduceddipole)) interac&ons) van)der)Waals)forces)

Decalin

Cis-‐decalin has a ring fusion where the second ring is a"ached by two cis bonds. Trans-‐decalin is fused using two trans bonds. Trans-‐decalin is more stable because the alkyl groups are equatorial.

Page 21: Arac&ve)Forces:)Boiling)and) …...... 36.1) C • Hexane)))))68.7) C • Heptane)))))98.4) C • Octane)))))125.7) C induceddipoleinduceddipole)) interac&ons) van)der)Waals)forces)

Bicyclic Systems

Page 22: Arac&ve)Forces:)Boiling)and) …...... 36.1) C • Hexane)))))68.7) C • Heptane)))))98.4) C • Octane)))))125.7) C induceddipoleinduceddipole)) interac&ons) van)der)Waals)forces)

Nomenclature of Bicyclic Systems

Bicyclo [#.#.#]alkane

Where # are the number of carbons on the bridges (in decreasing order) and the alkane name includes all the

carbons in the compound.

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