Department of Chemistry

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• Department of Chemistry
• CHEM1010 General Chemistry
• Instructor Dr. Hong Zhang
• Foster Hall, Room 221
• Tel [phone]
• Email hzhang_at_tntech.edu

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CHEM1010/General Chemistry_______________________
__________________Chapter 9. (L37)-Organic
Chemistry

• Todays Outline
• ..Alcohols
• ..Phenols
• ..Carboxylic acids

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Chapter 9. (L37)-Organic Chemistry

• Hydroxyl group and functional group
• Review of electronic structure of hydroxyl
  group, -OH
• Valence electronic structure of -OH
• ..
• OH
• ..
• -OH has one single unpaired electron available
  for bonding

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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
• CH3-OH, or CH3OH, methanol
• CH3CH2-OH, or CH3CH2OH, ethanol
• CH3CH2CH2-OH, or CH3CH2CH2OH,
• 1-propanol

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Chapter 9. (L37)-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

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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) 2H2 CH3OH
• a solvent, a chemical intermediate,
• can be used as a replacement for gasoline in
  automobiles

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Chapter 9. (L37)-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

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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

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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

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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.

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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

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Chapter 9. (L37)-Organic Chemistry

• Quiz Time
• Which of the following is an alcohol
• (a) CH3CH2OCH2CH3
• (b) CH3OCH2CH3
• (c) CH3CH2OH
• (d) CH3CH3.

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Chapter 9. (L37)-Organic Chemistry

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

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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

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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-OH or RCOOH

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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

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Chapter 9. (L37)-Organic Chemistry

• Carboxylic acids
• Examples of carboxylic acids
• R -CH3, acetic acid
• O
• CH3-C-OH or CH3COOH
• or ethanoic acid
• vinegar, 4-10 acetic acid solution

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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

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Chapter 9. (L37)-Organic Chemistry

• Quiz Time
• Which of the following is a carboxylic acid
• (a) CH3CH2OCH2CH3
• (b) CH3COCH2CH3
• (c) CH3CH2COOH
• (d) CH3CHO.

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Chapter 9. (L37)-Organic Chemistry

• Quiz Time
• Which of the following is acetic acid
• (a) CH3CH2OCH2CH3
• (b) CH3CH2COCH2CH3
• (c) HCOOH
• (d) CH3COOH.