1. Department of Chemistry CHEM1010 General Chemistry Instructor: Dr. Hong Zhang Foster Hall, Room 221 Tel: 931-6325 Email: hzhang@tntech.edu

2. CHEM1010/General Chemistry _________________________________________ Chapter 9. (L37)-Organic Chemistry Today’s Outline..Alcohols..Phenols..Carboxylic acids

3. Chapter 9. (L37)-Organic Chemistry Hydroxyl group and functional group …Review of electronic structure of hydroxyl group, -OH Valence electronic structure of -OH:.. ·O:H.. -OH has one single unpaired electron available for bonding

4. Chapter 9. (L37)-Organic Chemistry Alcohols …Alcohols are the hydrocarbons with one or more of H(s) replaced by –OH group(s) R-OH, their names are based on corresponding alkanes R- represents a carbon backbone Examples of alcohols CH 3 -OH, or CH 3 OH, methanol CH 3 CH 2 -OH, or CH 3 CH 2 OH, ethanol CH 3 CH 2 CH 2 -OH, or CH 3 CH 2 CH 2 OH, 1-propanol

5. Chapter 9. (L37)-Organic Chemistry Multifunctional Alcohols …Some Alcohols have more than one –OH group HO-R-OH, Examples of multifunctional alcohols HO-CH 2 -CH 2 -OH, or HOCH 2 CH 2 OH, ethylene glycol CH 3 -CH-CH 2, propylene glycol | | OH OH CH 2 CH-CH 2, | | | OH OH OH, glycerol

6. Chapter 9. (L37)-Organic Chemistry Alcohols …Methanol (methyl alcohol) the simplest alcohol also called wood alcohol, once made of wood modern industrial production: CO(g) + 2H 2 = CH 3 OH a solvent, a chemical intermediate, can be used as a replacement for gasoline in automobiles

7. Chapter 9. (L37)-Organic Chemistry Alcohols …Ethanol (ethyl alcohol) the simplest alcohol also called grain alcohol, can be made of grains via fermentation yeast C 6 H 12 O 6 = 2CH 3 CH 2 OH + 2CO 2 Industrial production: CH 2 =CH 2 + H 2 O + acid = CH 3 CH 2 OH industrially made ethanol cannot be used in beverages by law because of toxic impurities such as methanol

8. Chapter 9. (L37)-Organic Chemistry Alcohols …Ethanol (ethyl alcohol) gasoline in many parts of USA has up to 10% of ethanol from fermentation because of a large surplus of corn a solvent, a chemical intermediate, can be used as a replacement for gasoline in automobiles

9. Chapter 9. (L37)-Organic Chemistry Toxicity of alcohols …alcohols are generally toxic methanol can be oxidized in the living body to formaldehyde (HCHO). Drinking as little as 1 oz or ~30 mL or 2 table spoonfuls of methanol can cause blindness and even death 1 pint or ~500 mL of pure ethanol, rapidly ingested, will kill most people. alter brain cell functions, nerve damage, shorten life span, affecting babies from drunk mothers

10. Chapter 9. (L37)-Organic Chemistry Multifunctional alcohols …ethylene glycol is the main ingredient in many permanent antifreeze mixtures Propylene glycol is now used as a safer permanent antifreeze, not poisonous Glycerol is a sweet, syrupy liquid made as a by-product from fats during soap manufacture. It is used in lotions to keep the skin soft and as food addictive to keep cakes moist.

11. Chapter 9. (L37)-Organic Chemistry Phenols …Phenols are the organic compounds in which one or more –OH is attached to a benzene ring: benzene ring-OH, OH antiseptic, germicidal

12. Chapter 9. (L37)-Organic Chemistry Quiz Time Which of the following is an alcohol (a) CH 3 CH 2 OCH 2 CH 3 ; (b) CH 3 OCH 2 CH 3 ; (c) CH 3 CH 2 OH ; (d) CH 3 CH 3.

13. Chapter 9. (L37)-Organic Chemistry Quiz Time Which of the following is a phenol (a) CH 3 CH 2 OCH 2 CH 3 ; (b) CH 3 OCH 2 CH 3 ; (c) CH 3 CH 2 OH ; (d) -OH.

14. Chapter 9. (L37)-Organic Chemistry Review of electronic structure of oxygen …Review of electronic structure of oxygen Valence electronic structure of O.. O: or O=.. O can have two unpaired electrons available for bonding with C to form a double bond

15. Chapter 9. (L37)-Organic Chemistry Carboxylic acids Carboxylic acids are the hydrocarbons with the following functional group and structure: O ||carboxyl group -C-OH or-COOH General formula: O || R-C-OHor RCOOH

16. Chapter 9. (L37)-Organic Chemistry Carboxylic acids Examples of carboxylic acids R = -H, formic acid O || H-C-OH or HCOOH or methanoic acid first obtained by destructive distillation of ants

17. Chapter 9. (L37)-Organic Chemistry Carboxylic acids Examples of carboxylic acids R = -CH 3, acetic acid O || CH 3 -C-OH or CH 3 COOH or ethanoic acid vinegar, 4-10% acetic acid solution

18. Chapter 9. (L37)-Organic Chemistry More example of carboxylic acid O || Benzoic acid C-OH sodium benzoate is used as food addictive to prevent mold

19. Chapter 9. (L37)-Organic Chemistry Quiz Time Which of the following is a carboxylic acid (a) CH 3 CH 2 OCH 2 CH 3 ; (b) CH 3 COCH 2 CH 3 ; (c) CH 3 CH 2 COOH ; (d) CH 3 CHO.

20. Chapter 9. (L37)-Organic Chemistry Quiz Time Which of the following is acetic acid (a) CH 3 CH 2 OCH 2 CH 3 ; (b) CH 3 CH 2 COCH 2 CH 3 ; (c) H COOH ; (d) CH 3 COOH.