• Organic chemistry: the study of compounds based on carbon

  • Ex. of organic compounds: natural gas, rubbing alcohol, aspirin, compounds that give fragrance to rose

Chapter 1.1: Bonding and the Shape of Organic Molecules

• Organic compounds: compounds based on carbon; usually contains carbon-carbon and carbon-hydrogen bonds

• Million of organic compounds, only a quarter of million of inorganic compounds

• So many organic compounds because of carbon:

  • It forms four covalent bonds and connects to four other atoms

  • It forms strong single, double, or triple bonds with other carbons

• Saturated bonds: molecules that contain only single carbon-carbon bonds

• Unsaturated bonds: molecules that contain double or triple bonds

• Carbon unique bonding properties formation of chains and rings with a variety of sizes

• The shape of a molecule depends on the type of bond, examples include:

  • Carbon with four single bonds: tetrahedral shape

  • Carbon with one double bond and two singular bonds: trigonal planar shape

  • Carbon with two double bonds or one triple bond and one single bond: linear shape

  • Oxygen with two single bonds: bent shape

• 2-D diagrams good for condensed structural diagrams and line structures

• 3-D diagrams atoms are drawn with wedges to indicate it is in front, but lines when it is pushed back

• Polar covalent bond: the covalent bond between two atoms with different electronegativities

• Electronegativity: a measure of how strongly an atom attracts electrons in a chemical bond; partial negative or partial positive atom

• Every polar bond has a bond dipole

• Bond dipole: partial negative charge and partial positive charge, separated by the length of the bond

• Polar molecule or molecular polarity: when the molecule has an overall imbalance of charge

  • A molecule has a region with a partial positive charge and a region with a partial negative charge

  • Not all molecules with polar bonds are polar molecules

  • To determine molecular polarity, must consider the shape of molecule and bond dipoles within the molecule

• If equal bond dipoles act in opposite directions in three-dimensional space, they counteract each other

1.2 Hydrocarbons

• Hydrocarbons: simplest type of organic compounds, composed of entirely carbon and hydrogen atoms

  • Aliphatic hydrocarbons: contains carbon atoms that are bonded in one or more chains and rings

  • Aromatic hydrocarbons: based on aromatic benzene group

    • Benzene is the simplest aromatic compound

• Alkane: hydrocarbon that has only single bonds

  • CnH2n+2

  • Cycloalkane: alkane in a shape of a ring

    • CnH2n

• Alkene: hydrocarbon with at least one double bond

  • CnH2n

• Functional Group: a reactive group of bonded atoms that appears in all the members of a chemical family

• Alkyne: hydrocarbon with at least one triple bond

  • CnH2n-2

• Rules for Naming Organic Compounds:

  • Prefix + root + suffix

    • Root: number of carbon atoms in the main chain or ring

      • Number of carbon atoms:

        • 1: -meth-

        • 2: -eth-

        • 3: -prop-

        • 4: -but-

        • 5: -pent-

        • 6: -hex-

        • 7: -hept-

        • 8: -oct-

        • 9: -non-

        • 10: -dec-

    • Suffix: type of compound according to functional groups present

      • Alkanes: -ane

      • Alkenes: -ene

      • Alkynes: -yne

    • Prefix: indicates name and location of each branch and functional group on the main carbon chain

      • Alkyl group: removing one hydrogen from an alkane; branches attached to the main chan, common Alkyl groups:

        • Methyl

        • Ethyl

        • Propyl

        • Isopropyl

        • Butyl

        • Sec-butyl

        • Iso-butyl

        • Tert-butyl

• Aromatic compounds*:*** cyclic compound with alternating single and double bonds, such as benzene

Chapter 1.3: Single-Bonded Functional Groups

• OH (hydroxyl) group: a functional group that contains OH

• general formula: R+ functional, family of simple organic compounds

  • R' and R’’ are used for more than one alkyl group

• Compounds with the same functional group often have similar physical properties

• Compounds with the same functional group react chemically in very similar ways

• Common Functional Groups:

  • Alkane

  • Alkyne

  • Alcohol

  • Amine

  • Aldehyde

  • Ketone

  • Carboxylic acid

  • Ester

• Intermolecular forces: forces of attraction and repulsion between particles; organic compounds with the same functional groups have the same physical properties, which are often caused by intermolecular forces, which include:

  • Hydrogen bonding: strong intermolecular attraction between the hydrogen atom with an N, O, F atom

  • Dipole-Dipole interactions: attractive forces between polar molecules

  • Dispersion forces: attractive forces that occur between all covalent molecules

• Alcohol, alkyl halides, ethers, and amines are all functional groups with single bonds

• Alcohol: an organic compound that contains the -OH functional group

  • Alcohols are named after parent alkane

  • Parent alkane: alkane with the same basic carbon structure

  • Very polar due to O-H bond, soluble in water

  • Flammable and most are poisonous

• Alkyl halide/haloalkane: alkane in which one or more hydrogen atoms have been replaced with halogen atoms (F, Cl, Br, or I); R-X Similar properties to alcohols

• Ether: organic compound that has two alkyl groups joined by an oxygen atom; R-O-RAlkoxy group: alkyl singularly bonded to oxygen Less polar than water and alcoholUsually soluble in water but decreases as the alkyl group increasesLower boiling point than water

• Amine: An organic compound with the functional group -NH2, -NHR, or -NR2

  • Polar compounds

Chapter 1.4: Functional Groups With the C=O Bond

• Carbonyl group: carbon atom double-bonded to an oxygen atom; C=O

• Aldehyde: organic compound that has double-bonded oxygen on the last carbon of a carbon chain; R-CHO

• Ketone: organic compound that has double-bonded oxygen on any carbon within the carbon chain; RCOR’

  • Contains C=O, usually polar

  • Soluble in water

  • Boiling points lower than corresponding alcohols, but higher to corresponding alkanes

• Carboxylic acid: carbon atom is bonded to an oxygen atom by a double bond and to a hydroxyl group (-OH) by a single bond

  • Polar because of O-H and C=O bonds

  • Contains hydrogen bonds, which makes it have higher boiling points

  • If it has lower mass, then it becomes soluble in water

  • Decreases in solubility as carbon atom increases

  • Unpleasant odors

  • Carboxylic acid derivative: exchange in hydroxyl group of carboxylic acid with a different organic compound

• Carboxyl group: COOH group

• Ester is a derivative of carboxylic acid

• Ester: general formula for an ester is RCOOR’

  • R is a hydrogen atom or a hydrocarbon, and R′ is a hydrocarbon

  • Polar Molecule

  • Cannot form hydrogen bonds with other ester atoms, only with water

  • Low boiling point

  • Volatile at room temperature

• Amide: carbon atom double-bonded to an oxygen atom and single-bonded to a nitrogen atom

  • C-N and N-H bonds make it polar, acts like carboxylic acids

  • Stronger hydrogen bonds than carboxylic acids

  • Soluble in water

  • High melting and boiling points

  • Simple amides are solid at room temperature