1. Department of Chemistry CHEM1020 General Chemistry Summer/2006 *********************************************** Instructor: Dr. Hong Zhang Foster Hall, Room 221 Tel: 931-6325 Email: hzhang@tntech.edu

2. CHEM1020/General Chemistry/Summer, 2006 _________________________________________ Chapter 9. (L5)-Organic Chemistry Today’s Outline..Alcohols..Phenols..Ethers

3. Chapter 9. (L5)-Organic Chemistry Hydroxyl 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.. -OH is much like H or Cl in this way: ·H, ·Cl:..

4. Chapter 9. (L5)-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 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. (L5)-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. (L5)-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. (L5)-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. (L5)-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. (L5)-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. (L5)-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. (L5)-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 …Hydroquinone HO-benzene ring-OH, a common photographic developer

12. Chapter 9. (L5)-Organic Chemistry Ethers …Ethers are organic compounds with alkyl groups attached to the same oxygen atom: ROR, or ROR’ Examples: CH 3 CH 2 OCH 2 CH 3, diethyl ether, or simply ether a solvent, highly flammable, anesthetic with side effects such as nausea and vomiting New anesthetic ethers: Neothyl, methyl propyl ether, CH 3 OCH 2 CH 2 CH 3, Penthrane, methoxyflurane, CHCl 2 CF 2 OCH 3,

13. Chapter 9. (L5)-Organic Chemistry Ethers …MTBE CH 3 | CH 3 -O-C-CH 3 | CH 3 methyl tert-butyl ether, CH 3 OC(CH 3 ) 3 it was added to gasoline as an antiknock agent and to reduce emission of CO in automotive exhaust gas a pollutant

14. Chapter 9. (L5)-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.

15. Chapter 9. (L5)-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.

16. Chapter 9. (L5)-Organic Chemistry Quiz Time Which of the following is an ether (a) CH 3 CH 2 CH 3 ; (b) CH 3 OCH 2 CH 3 ; (c) CH 3 CH 2 OH ; (d) -OH.