ORGANIC CHEMISTRY

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ORGANIC CHEMISTRY

• The scientific study of the structure,
  properties, composition, reactions, and
  preparation (by synthesis or by other means) of
  chemical compounds consisting of primarily carbon
  and hydrogen, which may contain any number of
  other elements, including nitrogen, oxygen,
  halogens as well as phosphorus and sulfur.
• Wikipedia

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What is Organic Chemistry?

• Chemistry of the compounds of carbon- with a few
  exceptions (CO, CO2, carbonates, hydrogen
  carbonates cyanide and HCN)
• Many derived from living things and involved in
  life processes.
• About 8 million organic compounds known, but more
  than 3,500 new organic compounds are being
  reported every week.

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Functional Groups

• Determine the reactivity of organic compounds
• An atom or group of atoms which is characteristic
  of a class of organic compounds and which
  determines the properties of the class.
• Important in classifying or systemizing organic
  compounds
• Main Types of Functional Groups
• Hydrocarbons
• Polar Single Bonds
• Carbon-Oxygen Double Bonds

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Hydrocarbon Functional Groups

• Compounds which contain only carbon and hydrogen
• Three Main Types
• Aliphatic- Most hydrocarbons
• Alicyclic-Aliphatic compound which contains rings
  consisting of only carbon and hydrogen.
• Aromatic-Benzene like in character and properties

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Aliphatic Hydrocarbons

• Alkanes
• Characterized by having only single bonds
• Alkenes
• Characterized by having a carbon-carbon double
  bond
• Alkynes
• Characterized by having a carbon-carbon triple
  bond

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Alkanes

• Serve as a backbone for functional groups
• Nonpolar so are soluble in other nonpolar
  solutions
• Saturated compounds because they have full number
  of hydrogens
• Boiling point increase with number of carbons
• Straight and Branching chains
• Straight chains
• All names end in ane with prefix according to
  number of carbons (meth-1, eth-2, prop-3, but-4,
  pent-5, hex-6, hept-7, oct-8, non-9, dec-10)
• To write molecular formulas, use CnH2n2
• To draw structural formulas, write the symbol for
  carbon as many times as necessary and then fill
  in with hydrogens.

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• Branched Chain
• Alkyl group substituents, added to straight chain
  (use same prefix for number of carbons)
• Follow IUPAC rules for naming
• Find the longest chain of carbons in the molecule
  this will be the parent chain and end in ane
• Number the carbons in the parent chain, starting
  at the end where the most branches are.
• Determine substituents names and add numbers for
  where they appear on the parent chain.
• Use prefixes to indicate the appearance of a
  group more than once in the structure.
• For drawing structures draw carbons first then
  add hydrogens.
• Practice Problems 21 and 22 pg 1098

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Alkenes

• Hydrocarbons containing carbon-carbon double
  covalent bonds
• Unsaturated compounds because they dont have
  full number of hydrogens
• To name alkenes by IUPAC system
• Find longest chain that has double bond in it,
  use prefix from alkanes but add ene instead of
  ane
• Start numbering the parent chain from the end
  that makes the double bond have the lowest
  number.
• Follow other rules for alkanes but add a number
  at beginning of parent name to show where double
  bond is.
• Practice problem 23b and 24c pg 1098

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Alkynes

• Hydrocarbons containing carbon-carbon triple
  covalent bonds
• Unsaturated compounds because they dont have
  full number of hydrogens
• To name alkynes by IUPAC system use same rules as
  alkenes but use yne ending instead of ene.
• Pracitce problems 23d and 24b pg 1098

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Isomers

• Structural Isomers
• Compounds that have the same molecular formula
  but different molecular structures
• Differ in physical properties (BP MP) and
  reactivity
• Ex C4H10 can be butane or 2 methyl propane
• Geometric Isomers
• Differ only in the geometry of their
  substituents.
• Alkenes are fairly structured due to their double
  bonds. Therefore, there are two arrangements of
  the substituents, cis and trans, that are noted
  in naming.
• Cis configurations- place the substituents on the
  same side of the double bond
• Trans configurations-place the substituents on
  the oppostie sice of the double bond.

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• Stereoisomers
• Compounds of the same molecular structure that
  differ only in the arrangement of the atoms in
  space.
• Contain a asymmetrical carbon
• Compounds are nonsuperimposable mirror images of
  each other.
• Practice problems 14-15 pg 756

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Alicyclic

• In some cases, the two ends are attached to form
  a ring.
• Rings contain 3 to 20 carbons, but most are 5 or
  6 carbons.
• Naming for Alicyclic compounds are the same as
  alkanes except that you add cyclo to the front of
  the parent name.

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Aromatic

• Unsaturated rings of carbon that have double
  bonds so not as many hydrogens as possible.
• Benzene is the most simple form that has the
  molecular formula C6H6.
• Other aromatics either have the benzene as the
  parent part of the compound or the benzene is a
  substituent on a hydrocarbon chain.
• If the benzene is the main part of the compound,
  the substituents are then named as usual picking
  one of the substituents as position 1.
• If the benzene is a substituent is part of a
  chain then it is called a phenyl group.
• Practice problems 20 and 23 pg 761

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Polar Single Bond Functional Groups

• Compounds that only have single bonds but now
  include many other atoms in addition to carbon
  and hydrogen.
• Main Types include
• Halocarbons
• Alcohols and Phenols
• Ethers
• Amines

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Halocarbons

• Compounds of carbon and hydrogen that also
  contain covalently bonded fluorine, chlorine,
  bromine or iodine (halogens).
• These compounds are also called alkyl halides due
  to their common names.
• Have higher boiling points than hydrocarbons
• Using IUPAC naming rules, all have single bonds
  so parent chain name is the same as alkanes.
• Then the ine is taken off of the halogen and
  replaced with o and put in front of the parent
  name.
• A number is then placed in front of the halogen
  depending on where attaches to the chain.
• Practice problem 3 pg 777 and 22 pg 804

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Alcohols and Phenols

• Alcohol have a OH group attached to a carbon in a
  hydrocarbon chain and Phenols have an OH group
  attached to an aromatic hydrocarbon ring (benzene
  becomes benzenol).
• Boil at higher temps than hydrocarbons and
  halocarbons
• Some are soluble in water (those with 4 or less
  carbons).
• Both IUPAC and common names are used for
  Alcohols.
• Naming with IUPAC system find the longest chain
  of carbons that includes the one attached to the
  OH, replace the e of the parent name with ol.
• If there are more than 1 OH substituents the
  ending changes to 2-diol, 3-triol, 4-tetrol
• Common names have the alkyl group followed by
  alcohol. It can be a primary, secondary or
  tertiary alcohol due to the number of
  substituents attached to the carbon the OH is
  attached to.
• Practice problems 10 and 11 a b

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Ethers

• Compounds in which oxygen is bonded to two carbon
  groups or chains.
• Naming is fairly simple the alkyl groups
  attached to either side of the oxygen are named
  in alphabetical order and followed by the word
  ether.
• When both groups are the same on each side the
  ether is symmetrical and a di is put on the front
  of the name
• Practice problems 11 d c pg 784 27 pg 804

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Amines

• A compound that has a nitrogen attached to at
  least one hydrocarbon group.
• Primary amines only have one group
• (R-NH2)
• Secondary amines have two groups
• (R-NH-R)
• Tertiary amines have three groups
• (R-N-R)
• Naming is the same as ethers except you use the
  word amine instead of ether at the end

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Carbon-Oxygen Double Bond Functional Groups

• Compounds that contain a carbonyl group which is
  a carbon that is joined with an oxygen by a
  double bond.
• Main types include
• Aldehydes
• Ketones
• Carboxylic Acid
• Esters
• Amides

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Aldehydes

• Compound in which the carbon of the carbonyl
  group is always joined to at least one hydrogen.
• Those with 3 or less carbons are soluble in
  water.
• Have higher boiling points
• Using the IUPAC system, find the longest
  hydrocarbon chain that contains the carbonyl
  group. The e ending of the hydrocarbon is
  replaced by al.
• Practice problems 16 a c pg 794

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Ketones

• Compound in which the carbon of the carbonyl
  group is joined to two other hydrocarbon groups
• Using the IUPAC system, find the longest
  hydrocarbon chain that contains the carbonyl
  group. The e ending of the hydrocarbon is
  replaced by one.
• If the carbonyl group of a ketone could occur at
  several places on the chain, then its position is
  designated by the lowest possible number.
• Practice problem 16 b d pg 794

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Carboxylic Acids

• Compounds with a carboxyl group, which is a
  carbonyl group attached to a hydroxyl group (OH).
• Weak acids because they ionize only slightly in
  solution to give a carboxylate ion and a hydrogen
  ion.
• Using the IUPAC system, replace the e ending of
  the longest continuous carbon chain containing
  the carboxyl group with the ending oic acid.
• Many continuous chain carboxylic acids were first
  isolated from fats and are called fatty acids.
• Common names are often used more than IUPAC
  names. (Table 26.6 on pg 789)
• Practice problems 35 pg 805 (use both common and
  IUPAC names)

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Esters

• Compounds that contain a carbonyl group and an
  ether link to the carbonyl carbon.
• Many esters have pleasant, fruity odors and give
  most fruits their lovely odors.
• Lower boiling points
• Can be hydrolyzed by the addition of water to
  produce a carboxylic acid and an alcohol.
• Using the IUPAC system, find the longest chain
  that has the carboxyl group and add a oate on
  the end instead of an e.
• Add the alkyl group from the other side of the
  oxygen to the front of the parent name.

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Amides

• A compound that has a nitrogen attached to a
  carbonyl group.
• Primary amides only bond to hydrogens and the
  carbonyl group (carbonyl-NH2)
• Secondary amides have one hydrogen and one carbon
  group bonded to the nitrogen (carbonyl-NH-R)
• Tertiary amides have two carbon groups bonded to
  the nitrogen (carbonyl-N-R)

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Additional substituents

• Isopropyl
• Prefix iso is used when there is a methyl group
  on the carbon second from the unsubstituted end
  of the longest chain
• Isobutyl
• The carbon joining this alkyl group to another
  group is bonded to one other carbon, it is a
  primary carbon
• Sec-butyl
• The carbon joining this alkyl group to another
  group is bonded to two other carbons, it is a
  secondary carbon.
• Tert-butyl
• The carbon joining this alkyl group to another
  group is bonded to three other carbons, it is a
  tertiary carbon
• Vinyl
• When used as an alkl group in giving compounds
  common names ethene (without one hydrogen) is
  called a vinyl
• Phenyl
• When benzene is used as an alkyl group.