Chapter 1 - Classifying Organic Compounds

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