Hydrocarbon Derivatives

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• Hydrocarbon Derivatives
• And Functional Groups

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• Introduction
• Hydrocarbon derivatives are formed when one or
  more hydrogen atoms is replaced by an element or
  a group of elements other than hydrogen.
• Halogens (F2, Cl2, Br2, I2,) can all add to a
  hydrocarbon to form am alkyl halide.
• When naming the halogen the ine ending is
  replaced by o
• Fluorine becomes fluoro
• Chlorine becomes chloro
• Bromine becomes bromo
• Iodine becomes iodo

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• Common examples of organic halides.

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• Alkenes can also add to each other in an addition
  reaction to form long chains of carbon compounds.
• this is called polymerization
• The atom or group of atoms that are added to the
  hydrocarbon are called functional groups.
• Functional groups usually have multiple bonds or
  lone pairs of electrons that make them very
  reactive.

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• Alcohols
• An alcohol has a hydrogen replaced by a hydroxyl
  (-OH) group.
• The name of the hydrocarbon that was substituted
  determines the name of the alcohol.

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• The alcohol is named using the hydrocarbon name
  and adding the suffix ol.
• If methane is substituted with an OH group it
  becomes methanol
• If a pentane group is substituted with an OH
  group it is pentanol.
• For alcohols with more than two carbon atoms we
  need the number the chain so as to keep the
  alcohol group as low as possible.

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• Primary alcohols are those with the OH at the end
  of the Carbon chain.
• EX ethanol -------------------------------
  -----?
• 1-propanol -----------------------------
  ---------?
• Secondary alcohols are those having the OH within
  the Carbon chain.
• EX 2 - propanol -----------------------
  -------?

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• Tertiary alcohols are those that have the OH on
  a Carbon that has only C-C bonds
• EX 2 methyl 2- propanol

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• Gasoline is a mixture of hydrocarbons (C8H18 for
  example) that contain no atoms of oxygen. Gasohol
  contains ethyl alcohol, C2H5OH, which does
  contain oxygen.
• The addition of alcohol to gasoline, therefore,
  adds oxygen to the fuel. Since carbon monoxide
  forms when there is an insufficient supply of
  oxygen, the addition of alcohol to gasoline helps
  cut down on carbon monoxide emissions.

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• If an alcohol contains two OH groups it is a diol
  (sometimes called a glycol).
• An alcohol with three OH groups is called a triol
  (sometimes called a glycerol).

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Addition Reactions

• A substance is added to the double or triple bond
  of an alkene or alkyne.

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• The addition of water to an alkene is called a
  HYDRATION REACTION.

To make alcohol add water to ethene H H
H OH
CC H2O ? H C C H H H
H H
ethene water ethanol
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• The addition of HYDROGEN to an alkene is called a
  HYDROGENATION REACTION.

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• H H H H
• CC H2 ? H C C H
• H H H H
• ethene hydrogen ethane

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• Ethers,
• Aldehydes,
• and
• Ketones

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• Ethers
• An ether has a general formula R-O-R. Use
  ether ending.
• EX Diethyl ether C4H10O
• CH3CH2-O-CH2CH3

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• The best-known ether is the anesthetic called
  diethyl ether.
• Other ethers have a wide range of uses as
  solvents, refrigerants, artificial flavours, and
  drugs.
• As a class of compounds, ethers are relatively
  unreactive chemically.

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• Ethers are isometric with the alcohols.
• For example, diethyl ether (CH3CH2-O-CH2CH3) is
  an isomer of butanol (CH3CH2CH2CH2-OH).
• Both have the molecular formula C4H10O.

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Naming Ethers

• Ethers are named in two ways the common naming
  system, and the IUPAC naming system.

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• Common Names
• The alkyl groups attached to the ether linkage
  are named in alphabetical order and are followed
  by the word ether. Symmetrical ethers are named
  by using the prefix di-.
• IUPAC Names
• The carbon(s) attached to the oxygen atom are
  named as branches by adding the oxy suffix to
  the stem name.

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• Ex. CH3-CH2-CH2-CH2-O-CH2-CH3
• Common Name butyl ethyl ether
• IUPAC Name ethoxybutane

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Aldehydes and Ketones

• Two families of organic compounds, called
  aldehydes and ketones contain the carbonyl
  functional group (-CO).
• This group consists of a carbon atom double
  bonded to an oxygen atom.

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• An aldehyde has a carbonyl group (carbon double
  bonded to an oxygen) attached to a terminal
  carbon atom. Use al ending.
• EX Methanal CH2 O
• H2CO

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Uses of Aldehydes

• The smaller aldehyde molecules have sharp,
  irritating odours.
• The larger ones have flowery odours and are
  diluted to make perfumes.
• Methanal is a starting material in the
  manufacture of some plastics.

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• A ketone has a carbonyl group attached to an
  internal carbon atom. Use one ending.
• EX Propanone C3H6O
• CH3
• CO
• CH3

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• The carbonyl group (A) is present in both
  aldehydes and ketones, as shown in (B). (C) The
  simplest example of each, with the IUPAC name
  above and the common name below each formula.

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Uses of Ketones

• The simplest ketone is propanone (common name
  acetone).
• It is an effective solvent found in many nail
  polish removers, plastic cements, resins and
  varnishes.
• It is also sold as a cleaner. Because it is both
  volatile and flammable, it should be used only in
  well-ventilated areas.

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• Organic Acids
• and
• Esters

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Organic acids are those acids that are derived
from living organisms, usually from metabolism,
but sometimes as a defense mechanism. Long
chain organic acids are known as fatty acids.
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These are also called carboxylic acids as they
contain the carboxyl functional group (COOH)
One oxygen is double bonded to the carbon and
the other is bonded to the carbon and to the
hydrogen both with single bonds.
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• These red ants, like other ants, make the
  simplest of the organic acids, formic acid.
• The sting of bees, ants, and some plants contains
  formic acid, along with some other irritating
  materials. Formic acid is HCOOH.

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• Esters are condensation products of carboxylic
  acids with the removal of water (also called a
  dehydration synthesis).