Department of Chemistry CHEM1020 General Chemistry *********************************************** Instructor: Dr. Hong

1. Department of Chemistry CHEM1020 General Chemistry *********************************************** Instructor: Dr. Hong Zhang Foster Hall, Room 221 Tel: 931-6325 Email: hzhang@tntech.edu

2. CHEM1020/General Chemistry_________________________________________Chapter 9. (L7)-Organic Chemistry • Today’s Outline ..Esters ..Amines ..Amides ..Summary

3. Chapter 9. (L7)-Organic Chemistry • Esters Esters come from combination of carboxylic acids and alcohols or phenols: O O || || R–C–OH + R’OH  R–C–OR’ + H2O General formula: RCOOR’, or RCOOR

4. Chapter 9. (L7)-Organic Chemistry • Esters Naming esters: naming the part from the alcohol first followed by the part from the carboxylic acid with an end of –ate Example: CH3CH2CH2COOCH3, methyl butyrate CH3COOCH3, methyl acetate More examples on pp.263, Table 9.7

5. Chapter 9. (L7)-Organic Chemistry • Esters Properties of esters Esters tend to be fragrant, with fruity odors and tastes. Esters are widely used as flavorings in cakes, candies, and other foods and drinks and as ingredients in perfumes.

6. Chapter 9. (L7)-Organic Chemistry • Review of electronic structure of nitrogen …Review of electronic structure of oxygen Valence electronic structure of N: . . ·N· or –N– . | N can have three unpaired electrons available for bonding to form three bonds

7. Chapter 9. (L7)-Organic Chemistry • Review of electronic structure of ammonia …Review of electronic structure of ammonia Valence electronic structure of NH3: . . H:N:H or H–N–H .. | H H

8. Chapter 9. (L7)-Organic Chemistry • Amines ..Amines are formed from ammonia by replacing one, two, or three of the H in the NH3 with one , two ,or three alkyl groups, R, R’, or R”. General formulas for amines: R-NH2 R-NH-R, RNHR’ R-N-RR, R-NR’R, R-N-R’R”

9. Chapter 9. (L7)-Organic Chemistry • Amino group ..Amino group is formed from ammonia with one H removed: –NH2 We will learn more about amino groups and the organic compounds containing amino groups later in biochemistry.

10. Chapter 9. (L7)-Organic Chemistry • Amines ..Examples of amines: The simplest amine: RNH2, R = -CH3 CH3–NH2, methylamine More examples of amines: CH3CH2-NH2, ethylamine CH3NHCH3, dimethylamine ethylamine and dimethylamine are isomers sharing the same molecular formula: C2H7N (CH3)3N, trimethylamine

11. Chapter 9. (L7)-Organic Chemistry • More example of amine Aniline NH2 Aniline is used in making dyes. Aromatic amines tend to be toxic and some are strongly carcinogenic.

12. Chapter 9. (L7)-Organic Chemistry • Properties of amines Simple amines are similar to ammonia in odor, basicity, and other properties. Higher amines see book on pp.265, Fig. 9.15

13. Chapter 9. (L7)-Organic Chemistry • Amides Amide functional group: O || –C–N– |

14. Chapter 9. (L7)-Organic Chemistry • Amides General structural formulas for amides: O O O || || || R–C–NH2, R–C–NHR’, R–C–NR’R” In short cut: RCONH2, RCONHR’, RCONR’R”

15. Chapter 9. (L7)-Organic Chemistry • Amides Examples of amides: O O || || CH3–C–NH2, CH3–C–NHCH2CH3, Nylon, silk, and wool molecules contain hundreds of amide functional groups.

16. Chapter 9. (L7)-Organic Chemistry • Heterocyclic compounds Heterocyclic compounds are those cyclic hydrocarbons with C rings and N, O, and S atoms. Examples of heterocyclic compounds see book on pp.267

17. Chapter 9. (L7)-Organic Chemistry • Grand review Table 9.4, on book pp. 251 -basic concepts of organic chemistry -molecular formula -structural formula, simple and detailed -names of common organic compounds -functional groups -various kinds of organic compounds -common properties of organic compound

18. Chapter 9. (L7)-Organic Chemistry Quiz Time Which of the following is an ester (a) CH3CH2OCH2CH3; (b) CH3CH2COOCH2CH3; (c) CH3CH2OH; (d) CH3CHO.

19. Chapter 9. (L7)-Organic Chemistry Quiz Time Which of the following is an ester (a) CH3CH2OCH2CH3; (b) CH3CH2COOCH2CH3; (c) CH3CH2COCH2CH3; (d) CH3COOH.

20. Chapter 9. (L7)-Organic Chemistry Quiz Time Which of the following is an amine (a) CH3CH2OCH2CH3; (b) CH3CH2COOCH2CH3; (c) CH3CH2NHCH2CH3; (d) NH3.

21. Chapter 9. (L7)-Organic Chemistry Quiz Time Which of the following is an amine (a) CH3CH2OCH2CH3; (b) CH3CH2COOCH2CH3; (c) CH3CH2NH2; (d) NH3.

22. Chapter 9. (L7)-Organic Chemistry Quiz Time Which of the following is an amine (a) CH3CH2OCH2CH3; (b) (CH3CH2)3N; (c) CH3CH2OH; (d) NH3.

23. Chapter 9. (L7)-Organic Chemistry Quiz Time Which of the following is an amide (a) CH3CH2OCH2CH3; (b) (CH3CH2)3N; (c) CH3CH2CONH2; (d) NH3.

24. Chapter 9. (L7)-Organic Chemistry Quiz Time Which of the following is an amide (a) CH3CH2OCH2CH3; (b) (CH3CH2)3N; (c) CH3CH2CONHCH3; (d) NH3.

25. Chapter 9. (L7)-Organic Chemistry Quiz Time Which of the following is an amide (a) CH3CH2OCH2CH3; (b) (CH3CH2)3N; (c) CH3CH2CON(CH3)2; (d) NH3.

26. Chapter 9. (L7)-Organic Chemistry Quiz Time Which of the following is an ethylmethylamine (a) CH3CH2OCH2CH3; (b) (CH3CH2)3N; (c) CH3CH2NHCH3; (d) CH3CH2NHCH2CH3.