1. 10 10-1 © 2003 Thomson Learning, Inc. All rights reserved General, Organic, and Biochemistry, 7e Bettelheim, Brown, and March

2. 10 10-2 © 2003 Thomson Learning, Inc. All rights reserved Chapter 10 Organic Chemistry Organic Chemistry

3. 10 10-3 © 2003 Thomson Learning, Inc. All rights reserved Organic Chemistry 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. 10 10-4 © 2003 Thomson Learning, Inc. All rights reserved Organic Chemistry Why is organic chemistry a separate discipline within chemistry? historical: 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. 10 10-5 © 2003 Thomson Learning, Inc. All rights reserved Organic Chemistry The sheer number of organic compounds 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 The link to biochemistry carbohydrates, lipids, proteins, enzymes, nucleic acids, hormones, vitamins, and almost all other chemicals in living systems are organic compounds

6. 10 10-6 © 2003 Thomson Learning, Inc. All rights reserved Organic Chemistry a comparison of organic and inorganic compounds

7. 10 10-7 © 2003 Thomson Learning, Inc. All rights reserved Organic Structure structural formula:structural formula: shows the atoms present in a molecule as well as the bonds that connect them VSEPR model:VSEPR model: the most common bond angles are 109.5°, 120°, and 180°

8. 10 10-8 © 2003 Thomson Learning, Inc. All rights reserved Organic Structure Among neutral (uncharged) organic compounds carbon:carbon: four covalent bonds and no unshared pairs of electrons hydrogen:hydrogen: one covalent bond and no unshared pairs of electrons nitrogen:nitrogen: three covalent bonds and one unshared pair of electrons oxygen:oxygen: two covalent bonds and two unshared pairs of electrons a halogen:a halogen: one covalent bond and three unshared pairs of electrons

9. 10 10-9 © 2003 Thomson Learning, Inc. All rights reserved Functional Groups Functional group: 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. 10 10-10 © 2003 Thomson Learning, Inc. All rights reserved Functional Groups Five important functional groups

11. 10 10-11 © 2003 Thomson Learning, Inc. All rights reserved Alcohols Alcohol: Alcohol: contains an OH (hydroxyl) group bonded to a tetrahedral carbon atom may be primary (1°), secondary (2°), or tertiary (3°)

12. 10 10-12 © 2003 Thomson Learning, Inc. All rights reserved Alcohols Problem: Problem: draw Lewis structures and condensed structural formulas for the two alcohols of molecular formula C 3 H 8 O

13. 10 10-13 © 2003 Thomson Learning, Inc. All rights reserved Alcohols Problem: Problem: draw Lewis structures and condensed structural formulas for the two alcohols of molecular formula C 3 H 8 O Solution: Solution:

14. 10 10-14 © 2003 Thomson Learning, Inc. All rights reserved Amines Amine:amino group Amine: a compound containing an amino group the amino group may be primary (1°), secondary (2°), or tertiary (3°)

15. 10 10-15 © 2003 Thomson Learning, Inc. All rights reserved Amines Problem:Problem: draw condensed structural formulas for the two primary amines of molecular formula C 3 H 9 N

16. 10 10-16 © 2003 Thomson Learning, Inc. All rights reserved Amines Problem:Problem: draw condensed structural formulas for the two primary amines of molecular formula C 3 H 9 N Solution:Solution:

17. 10 10-17 © 2003 Thomson Learning, Inc. All rights reserved Aldehydes and Ketones C=O (carbonyl) group Both contain a C=O (carbonyl) group aldehyde:aldehyde: contains a carbonyl group bonded to a hydrogen; in formaldehyde, the simplest aldehyde, the carbonyl group is bonded to two hydrogens ketone:ketone: contains a carbonyl group bonded to two carbon atoms

18. 10 10-18 © 2003 Thomson Learning, Inc. All rights reserved Aldehydes and Ketones Problem:Problem: draw condensed structural formulas for the two aldehydes of molecular formula C 4 H 8 O

19. 10 10-19 © 2003 Thomson Learning, Inc. All rights reserved Aldehydes and Ketones Problem:Problem: draw condensed structural formulas for the two aldehydes of molecular formula C 4 H 8 O Solution: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. 10 10-20 © 2003 Thomson Learning, Inc. All rights reserved Carboxylic Acids Carboxylic acid: a compound containing carboxyl Carboxylic acid: a compound containing a -COOH (carboxyl: carbonyl + hydroxyl) group in a condensed structural formula, a carboxyl group may also be written -CO 2 H.

21. 10 10-21 © 2003 Thomson Learning, Inc. All rights reserved Carboxylic Acids Problem:Problem: draw a condensed structural formula for the single carboxylic acid of molecular formula C 3 H 6 O 2

22. 10 10-22 © 2003 Thomson Learning, Inc. All rights reserved Carboxylic Acids Problem:Problem: draw a condensed structural formula for the single carboxylic acid of molecular formula C 3 H 6 O 2 Solution: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. 10 10-23 © 2003 Thomson Learning, Inc. All rights reserved Chapter 10 Organic Chemistry End Chapter 10