General, Organic, and Biochemistry, 7e

1. General, Organic, and Biochemistry, 7e Bettelheim, Brown, and March

2. Chapter 10 Organic Chemistry

3. 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 are sulfur, phosphorus, and a halogen (fluorine, chlorine, bromine, or iodine)

4. 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

5. 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

6. Organic Chemistry • a comparison of organic and inorganic compounds

7. Organic Structure • structural formula: shows the atoms present in a molecule as well as the bonds that connect them • VSEPR model: the most common bond angles are 109.5°, 120°, and 180°

8. Organic Structure • Among neutral (uncharged) organic compounds • carbon: four covalent bonds and no unshared pairs of electrons • hydrogen: one covalent bond and no unshared pairs of electrons • nitrogen: three covalent bonds and one unshared pair of electrons • oxygen: two covalent bonds and two unshared pairs of electrons • a halogen: one covalent bond and three unshared pairs of electrons

9. Functional Groups • Functional group: a part of an organic molecule that undergoes chemical reaction • Functional groups are important because • they undergo the same types of chemical reactions no matter in which 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

10. Functional Groups • Five important functional groups

11. Alcohols • Alcohol: contains an OH (hydroxyl) group bonded to a tetrahedral carbon atom • may be primary (1°), secondary (2°), or tertiary (3°)

12. Alcohols • Problem: draw Lewis structures and condensed structural formulas for the two alcohols of molecular formula C3H8O

13. Alcohols • Problem: draw Lewis structures and condensed structural formulas for the two alcohols of molecular formula C3H8O • Solution:

14. Amines • Amine: a compound containing an amino group • the amino group may be primary (1°), secondary (2°), or tertiary (3°)

15. Amines • Problem: draw condensed structural formulas for the two primary amines of molecular formula C3H9N

16. Amines • Problem: draw condensed structural formulas for the two primary amines of molecular formula C3H9N • Solution:

17. Aldehydes and Ketones • Both contain 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

18. Aldehydes and Ketones • Problem:draw condensed structural formulas for the two aldehydes of molecular formula C4H8O

19. Aldehydes and Ketones • Problem:draw condensed structural formulas for the two aldehydes of 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.

20. Carboxylic Acids • Carboxylic acid: a compound containinga -COOH (carboxyl: carbonyl + hydroxyl) group • in a condensed structural formula, a carboxyl group may also be written -CO2H.

21. Carboxylic Acids • Problem:draw a condensed structural formula for the single carboxylic acid of molecular formula C3H6O2

22. Carboxylic Acids • Problem:draw a condensed structural formula for the single carboxylic acid of 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

23. Chapter 10 Organic Chemistry End Chapter 10