Organic Chemistry

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Organic Chemistry

• a branch of chemistry concerned with the study of
  carbon and its compounds.

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Hydrocarbons

• the simplest class of organic compounds
  containing carbon hydrogen only

hydrocarbons
alkanes
cycloalkanes
alkenes
alkynes
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Aliphatic Hydrocarbons

• A hydrocarbon with no aromatic ring
• Example

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Aromatic Hydrocarbons

• a hydrocarbon containing one or more rings with
  delocalized ? electron systems
• (example is benzene, C6H6)

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Alkanes

• are saturated hydrocarbons
• general formula is CnH2n2
• ex CH4 (methane)
• single covalent bonds (C-C) between carbon to
  carbon molecules are present
• uses the ane ending in its name

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Alkanes

• The first 10 alkanes are named as follows
• CH4 methane C6H14 hexane
• C2H6 ethane C7H16 heptane
• C3H8 propane C8H18 octane
• C4H10 butane C9H20 nonane
• C5H12 pentane C10H22 decane

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Cycloalkanes

•  alkanes whose carbon atoms are joined in rings
•  general formula is CnH2n
• ex C6H12 (cyclohexane)
• uses the prefix cyclo and ane ending in its name

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Alkenes (Olefins)

• unsaturated hydrocarbons that contain CC
• general formula is CnH2n (same as cyloalkane)
• exC2H4 (ethene)
• uses the ene ending in its name

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Alkynes (Paraffins)

• unsaturated hydrocarbons that contain C?C
• general formula is CnH2n-2
• ex C2H2 (ethyne)
• uses the yne ending in its name

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Important Notes

• an alkane less one hydrogen atom is called an
  alkyl group (example is when a hydrogen atom is
  removed from methane, it is called methyl, -CH3)

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Naming Alkanes

• Step 1
• Determine the parent name by finding the longest
  continuous chain of carbon atoms in the molecule.
  The parent name is the name of the alkane
  corresponding to the longest continuous carbon
  chain. The longest chain may not be always
  written horizontally.

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Naming Alkanes
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Naming Alkanes

• If the molecule contains two chains of equal
  length, choose the one with the greater number of
  substituents as the parent chain.

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Naming Alkanes

•  Step 2
• name each substituent and precede this name with
  the number of carbon atom on the parent chain to
  which it is bonded.

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Naming Alkanes

•  
•  
• Parent butane
• Substituent methyl
• Location C2- methyl
• Name 2 methylbutane

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Naming Alkanes

• Two or more identical substituents present in a
  molecule are indicated by the use of the prefixes
  di for 2, tri for 3 tetra for 4, etc. Each of the
  identical substituents must have a number

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Naming Alkanes

• Parent butane
• Substituent methyl
• Location C2 and C3- methyl
• Name 2,3 dimethylbutane

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Naming Alkanes

• When two or more substituents are present, their
  names are listed in alphabetical order

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Naming Alkanes

•  
• Parent heptane
• Substituent methyl and ethyl
• Location C2- methyl and C3- ethyl
• Name 3 ethyl 2 methylheptane
• Note the name of the compound is written in
  single word.

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Naming Alkenes Alkynes

• Step 1
• Choose the longest continuous carbon chain that
  contains the double/triple bond as the parent
  chain.
• Step 2
• Number the chain to give the lowest number to the
  first carbon of the double/triple bond.

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Naming Alkenes Alkynes

• Step 3
• Substitute the ending -ene for ending ane in
  the name of the corresponding alkane to obtain
  the parent alkene name and substitute yne to
  obtain the parent alkyne. The position of the
  double/triple bond is indicated by a number.
• Step 4
• Write the complete name of the compound with the
  correct number of all substituents, which are
  listed in alphabetical order.

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Examples

• Parent octene
• Location C3
• Substituent methyl, ethyl bromo
• Location C3,C6- methyl C4 bromo C6-ethyl
• Name4-Bromo6-ethyl-3,6-dimethyl-3-octene

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Examples

• Parent butyne
• Location C1
• Substituent methyl
• Location C3
• Name 3 methyl 1- butyne
• or 3- methylbutyne

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Aromatics Benzene

• Monosubstituted benzenes are named by combining
  the substituent name w/ the word benzene.
• Name 1 - ethylbenzene

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• For disubstituted benzenes the 3 possible isomers
  are named using the prefixes ortho (o), meta (m)
  para (p) to designate the 1,2 1,3 1,4
  relationships of sustituents on the benzene
  ring
• Name 1,3-Dibromobenzene
• or meta-Dibromobenzene

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Exercises

• Draw the structure of the following hydrocarbons
• 2,2-dimethylpentane
• 4-ethyl-2,3-dimethyloctane
• 3-ethyl-3-methyl-1-pentene
• 1,3- dibromobenzene

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Exercises

• Give the name of the following Hydrocarbons
• 1.
• 2.

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• 3. 4.
  
  
• 5. 6.

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Hydrocarbon Derivatives

• these are compounds that are formed when one, two
  or three hydrogen atoms in the hydrocarbon
  molecules are replaced by atoms or group of atoms
  that are responsible for the properties of that
  compound. This group of atoms is called the
  functional group.

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ALCOHOLS

• Contains the OH group (hydroxyl)
• ex
• CH3-OH methanol
• CH3CH2-OH ethanol
• phenol

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Some Typical Alcohols

• OH
• rubbing alcohol CH3CHCH3
• 2-propanol (isopropyl alcohol)
• antifreeze HO-CH2-CH2-OH
• 1,2-ethanediol (ethylene glycol)
• OH
• glycerol HO-CH2-CH-CH2OH

Anti-freeze
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Ethers

• Contain an -O- between two carbon groups
• CH3-O-CH3 dimethyl ether
• CH3-O-CH2CH3 ethyl methyl ether

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Aldehydes and Ketones

• In an aldehyde, an H atom is attached to a
  carbonyl group
• O carbonyl group
• ?
• CH3-C-H
• In a ketone, two carbon groups are attached to a
  carbonyl group
• O carbonyl group
• ?
• CH3-C-CH3

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Aldehydes as Flavorings
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Ketones
O O ? ? Butter
flavor CH3-C-C-CH3 butanedione
propanone
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Amines

• Organic compounds of nitrogen N
• Classified as primary, secondary, tertiary
• CH3 CH3
• ? ?
• CH3NH2 CH3NH CH3N CH3
• 1 2 3

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Alkaloids

• Physiologically active nitrogen-containing
  compounds
• Obtained from plants
• Used as anesthetics, antidepressants, and
  stimulants
• Many are addictive

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Some Common Amines
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Some Common Amines
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Carboxylic Acid
Carboxylic acids contain the carboxyl group on
carbon 1. O ?? CH3
COH CH3COOH carboxyl group
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Some Carboxylic Acids their Names

Citric acid
Aspirin
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Amides
Derivatives of carboxylic acids where an amino
(-NH2) group replaces the OH group.
O O ?? ?? CH3
COH CH3 CNH2 carboxylic acid
amide acetic acid acetamide
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Some Amides their Names

• O
• ??
• CH3CNHCH3 N-methylethanamide (IUPAC)
• N-methylacetamide (common)

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Esters
In an ester, the H in the carboxyl group is
replaced with an alkyl group O
?? CH3 CO CH3 CH3COO CH3
ester group
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Esters in Plants
Esters give flowers and fruits their pleasant
fragrances and flavors.
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Some Esters and Their Names
Flavor/Odor Raspberries HCOOCH2CH3 ethyl
methanoate (IUPAC) ethyl formate
(common) Pineapples CH3CH2CH2
COOCH2CH3 ethyl butanoate (IUPAC) ethyl
butyrate (common)
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Exercises
Identify the functional groups present in the
following compounds
(2)
(4)
(1)
(3)
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(7)
(5)
(8)
(6)
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