Chapter 10 Organic Chemistry

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Organic Chemistry Organic chemistry: The study of the compounds of carbon. Organic compounds are made up of carbon and only a few other elements. Chief among these are hydrogen, oxygen, and nitrogen. Also present in some organic compounds are sulfur, phosphorus, and a halogen (fluorine, chlorine, bromine, or iodine).

Organic Chemistry Why is organic chemistry a separate discipline within chemistry? Historical: Scientists at one time believed that a “vital force” present in living organisms was necessary to produce an organic compound. The experiment of Wöhler in 1828 was the first in a series of experiments that led to the demise of the vital force theory.

Organic Chemistry The sheer number of organic compounds Chemists have discovered or made over 10 million organic compounds and an estimated 100,000 new ones are discovered or made each year. By comparison, chemists have discovered or made an estimated 1.7 million inorganic compounds. Thus, approximately 85% of all known compounds are organic. The link to biochemistry Carbohydrates, lipids, proteins, enzymes, nucleic acids, hormones, vitamins, and almost all other chemicals in living systems are organic compounds.

Organic Chemistry A comparison of organic and inorganic compounds

Organic Structure Structural formula: Shows the atoms present in a molecule and the bonds that connect them. VSEPR model: The most common bond angles are 109.5°, 120°, and 180°.

Organic Structure Among neutral (uncharged) organic compounds: Carbon normally forms four covalent bonds and has no unshared pairs of electrons. Hydrogen forms one covalent bond and no unshared pairs of electrons. Nitrogen normally forms three covalent bonds and has one unshared pair of electrons. Oxygen normally forms two covalent bonds and has two unshared pairs of electrons. Halogen normally forms one covalent bond and has three unshared pairs of electrons.

Functional Groups Functional group: An atom or group of atoms within a molecule that shows a characteristic set of predictable physical and chemical properties. Functional groups are important because They undergo the same types of chemical reactions no matter in what organic molecule they are found. To a large measure, they determine the chemical and physical properties of a molecule. They are the units by which we divide organic compounds into families. They provide the basis on which we derive names for organic compounds.

Functional Groups

Alcohols Alcohol: Contains an —OH (hydroxyl) group bonded to a tetrahedral carbon atom. For example, ethanol: Alcohols are classified as primary (1°), secondary (2°), or tertiary (3°).

Important Definition R group: An abbreviation for any group of atoms that may include carbons, hydrogens, halogens, oxygens and nitrogens that are attached to a functional group or represent a side chain to the rest of a molecule.

Alcohols Problem: Draw Lewis structures and condensed structural formulas for the two alcohols with the molecular formula C3H8O.

Alcohols Problem: Draw Lewis structures and condensed structural formulas for the two alcohols with the molecular formula C3H8O. Solution:

Amines Amine: A compound containing an amino group (-NH2, RNH2, R2NH, R3N). Amino groups are classified as primary (1°), secondary (2°), or tertiary (3°).

Amines Problem: Draw condensed structural formulas for the two primary amines with the molecular formula C3H9N.

Amines Problem: Draw condensed structural formulas for the two primary amines with the molecular formula C3H9N. Solution:

Aldehydes and Ketones Each contains a C=O (carbonyl) group. Aldehyde: Contains a carbonyl group bonded to a hydrogen; in formaldehyde, the simplest aldehyde, the carbonyl group is bonded to two hydrogens. Ketone: Contains a carbonyl group bonded to two carbon atoms.

Aldehydes and Ketones Problem: Draw condensed structural formulas for the two aldehydes with the molecular formula C4H8O.

Aldehydes and Ketones Problem: Draw condensed structural formulas for the two aldehydes with the molecular formula C4H8O. Solution: First draw the functional group of an aldehyde and add the remaining three carbons; these may be bonded in two ways. Then add the seven hydrogens necessary to complete the four bonds of each carbon.

Carboxylic Acids Carboxylic acid: A compound containing a -COOH (carboxyl: carbonyl + hydroxyl) group. In a condensed structural formula, a carboxyl group may also be written -CO2H.

Carboxylic Acids Problem: Draw a condensed structural formula for the single carboxylic acid with the molecular formula C3H6O2.

Carboxylic Acids Problem: Draw a condensed structural formula for the single carboxylic acid with the molecular formula C3H6O2 Solution: The only way the carbon atoms can be written is three in a chain; the -COOH group must be on an end carbon of the chain.

Carboxylic Ester Carboxylic ester: A derivative of a carboxylic acid in which the H of the carboxyl group is replaced by a carbon group.

Carboxylic Amide Amide: A derivative of a carboxylic acid in which the —OH of the carboxyl group is replaced by an amino group.

Carboxylic Acids Problem: Draw a condensed structural formula for the single carboxylic acid with the molecular formula C3H6O2 Solution: The only way the carbon atoms can be written is three in a chain; the -COOH group must be on an end carbon of the chain.

Chapter 10 Organic Chemistry End Chapter 10