Department of Chemistry

1

• Department of Chemistry
• CHEM1020 General Chemistry
• Summer/2006
• Instructor Dr. Hong Zhang
• Foster Hall, Room 221
• Tel [phone]
• Email hzhang_at_tntech.edu

2
CHEM1020/General Chemistry/Summer,
2006_________________________________________Cha
pter 9. (L5)-Organic Chemistry

• Todays 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
• ..
• OH
• ..
• -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
• CH3-OH, or CH3OH, methanol
• CH3CH2-OH, or CH3CH2OH, ethanol
• CH3CH2CH2-OH, or CH3CH2CH2OH,
• 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-CH2-CH2-OH, or HOCH2CH2OH,
• ethylene glycol
• CH3-CH-CH2, propylene glycol
• OH OH
• CH2CH-CH2,
• 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) 2H2 CH3OH
• 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
• C6H12O6 2CH3CH2OH 2CO2
• Industrial production
• CH2CH2 H2O acid CH3CH2OH
• 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
• CH3CH2OCH2CH3, 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, CH3OCH2CH2CH3,
• Penthrane, methoxyflurane, CHCl2CF2OCH3,

13
Chapter 9. (L5)-Organic Chemistry

• Ethers
• MTBE
• CH3
• CH3-O-C-CH3
• CH3
• methyl tert-butyl ether, CH3OC(CH3)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) CH3CH2OCH2CH3
• (b) CH3OCH2CH3
• (c) CH3CH2OH
• (d) CH3CH3.

15
Chapter 9. (L5)-Organic Chemistry

• Quiz Time
• Which of the following is a phenol
• (a) CH3CH2OCH2CH3
• (b) CH3OCH2CH3
• (c) CH3CH2OH
• (d) -OH.

16
Chapter 9. (L5)-Organic Chemistry

• Quiz Time
• Which of the following is an ether
• (a) CH3CH2CH3
• (b) CH3OCH2CH3
• (c) CH3CH2OH
• (d) -OH.