Organic Chemistry

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Organic Chemistry

• Organic Families
• Part I

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Organic Families Alcohols
Methyl, an alkyl group
Methanol, an alcohol (alkly hydroxyl)
Methane
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Organic Families Alcohols
Ethanol
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Organic Families Alcohols
2-propanol (isopropyl alcohol rubbing alcohol)
1-propanol
Your nose can tell the difference!
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Organic Families Alcohols
1-pentanol
2-pentanol
3-pentanol
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Organic Families Alcohols
Primary
Secondary
Tertiary
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Some Alcohols at Home
Are generally toxic if ingested!
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Organic Families Alcohols

• Alcohol a hydroxyl in place of -H in an alkane
• General formula R-OH ( R is any alkyl group)
• Classes
• Primary one alkyl group on CH2OH
• Secondary two alkyl groups on CH2OH
• Tertiary three alkyl groups on CH2OH
• Alcohol of 1-4 carbons very soluble in water of
  5 -7 carbons slightly soluble in water of 8 or
  more carbons are not soluble in water

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Organic Families Alcohols

• Hydroxyl group with oxygen and hydrogen can form
  hydrogen bonds so may make an organic compound
  polar
• Hydroxyl group is important in sugars, starches
  and steroids including cholesterol

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Organic Families Phenols
Phenol benzene ring with hydroxyl
Menthol
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Some Phenols at Home
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Organic Families Phenols

• Phenol a hydroxyl in place of -H on a benzene
  ring
• In water, phenols ionize slightly as a weak acid
• Concentrated solutions of phenols are corrosive

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Organic Families Thiols
-SH
-OH
Thiol (methanethiol)
Alcohol (methanol)
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Organic Families Thiols
CH3-SH in osyters and cheese
CH3-CH2-CH2-SH in onions
CH2CH-CH2-SH in garlic
-SH gives us the strong odors of skunks and these
foods
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Organic Families Thiols

• Thiol a -SH in place of -OH
• Short-chain thiols have a disagreeable odor
• Important in proteins

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Organic Families Ethers
Dimethyl ether
Ether Group
Ethyl methyl ether
Methyl phenyl ether
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Organic Families Ethers

• Ether contains an oxygen atom that is attached
  by single bonds to two carbons
• Has oxygen so can hydrogen bond with water
• Diethyl ether was used as an anesthetic for more
  than a hundred years it is volatile and
  flammable
• Newer anesthetics have ether group that has side
  effects in humans so use halothane

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Hydrogen Bonding in Organics
Ethers do not hydrogen bond to each other
Hydroxyls hydrogen bond to each other
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Hydrogen Bonding in Organics
Hydroxyls hydrogen bond to water
Ethers hydrogen bond to water
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Organic Families Ethers

• Short-chain ethers are soluble in water like
  alcohols because of hydrogen bonding
• Dimethyl ether is soluble in water
• Diethyl ether is slightly soluble in water
• Ethers have boiling points more like alkanes
  because ethers do not hydrogen bond to each other
  
• Need more energy to break hydrogen bonds
• Alcohols have higher boiling points than alkanes
  and ethers

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Organic Families Carbonyl Group
Dipole to dipole bond (increases boiling point)
Strong polarity (water soluble)
Carbon double-bonded to oxygen (responsible for
wide variety of flavors and odors)
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Organic Families Aldehydes and Ketones
O CH3 - CH2 - C - H or CH3 - CH2 - C -
OH
O CH3 - C - CH3 or CH3
CO - CH3
Aldehyde carbonyl attached to and end C
(carbonyl has a hydrogen)
Ketone carbonyl not on an end C
(carbonyl attached to two alkyls or aromatic
rings)
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Some Carbonyls in the Home
Aldehydes
Ketones
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Organic Families

• Aldehydes and ketones have similar properites
  polar 1 to 4 Cs are water soluble
• Also very different
• Tollens test AgNO3 in ammonia oxides aldehydes
  but not ketones
• Primary alcohol oxides to aldehyde secondary
  alcohol oxides to ketone
• Aldehydes oxidize to carboxylic acids ketones do
  not oxidize

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Organic Families Aldehydes
Methanal (formaldehyde)
Ethanal (acetaldehyde)
Propanal
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Organic Families Aldehydes

• Formaldehyde colorless gas with pungent odor
• Reactant in sythesis of polyers
• Formulin (40 formaldehyde in water) is a
  germicide
• Benzaldehydes give odor to cinnamon, almond and
  vanilla
• Aldehydes are used to flavor food and as
  fragrances in perfumes

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Organic Families Ketones
Propanone (acetone)
Butanone
Cyclopentanone
Butanedione (butter flavor)
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Organic Families Ketones

• Acetone colorless liquid with mild odor
• In cleaning fluids, paint remover, nail polish
  remover, rubber cement
• Produced in the body when high amount of fats are
  burned for energy gives fruity odor to breath
• Dihydroyacetone in sunless tanning lotions
  darkens the skin
• Butanedione gives the flavor of butter

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Why does vanilla appear more than once?
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Ether
?
Phenyl
?
Hydroxyl
?
Aldehyde