Unit 4: Organic Chemistry

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Organic Chemistry
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– Chemistry of compound that contain CARBON. – usually contain H – often contain O – sometimes contain S, N, P, and halogens – all are covalent
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Organic Compound
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– have covalent bonds – soluble in non-polar solvent. – non-electrolytes. – have low melting and boiling points. – burn easily. – grater in number. (more than 3 million known organic compounds.)
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Inorganic Compound
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– have ionic bonds. – soluble in polar solvents. – electrolyte. – have high melting and boiling points. – do not burn easily. – fewer in number (several hundred thousand known inorganic compounds.)
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Molecular formula
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gives the symbol for each type of atom in one molecule of a compound (i.e. C₃H₈)
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Full structural formula
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2D representation of the molecule showing which atoms are bonded to which
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Condensed structural formula
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gives the structure for the molecule but in condensed for (i.e. CH₃CH₃ = ethane)
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Types of Carbon
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– primary carbon – secondary carbon – tertiary carbon – quaternary carbon
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Primary (1⁰) Carbon
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only one of its 4 bonds is to another carbon.
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Secondary (2°) Carbon
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two of its 4 bonds are to other carbon atoms.
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Tertiary (3°) Carbon
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three of its 4 bonds are to other carbon atoms.
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Quaternary (4°) Carbon
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all four of its 4 bonds are to other carbon atoms.
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Classes of Organic Compounds
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– Alkanes – Alkenes – Alkynes – Alcohol – Ether – Aldehyde – Ketone – Carboxylic acid – Ester – Amine – Amide
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Hydrocarbons
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-organic compounds that contain only C and H. -the chief source of hydrocarbon is PETROLEUM. (definitely nonpolar) – Aliphatic hydrocarbons – Aromatic hydrocarbons
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Aliphatic Hydrocarbons
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– alkanes, alkenes, and alkynes – mostly insoluble in water because they are nonpolar (hexane is a common organic solvent) – smaller mass (fewer carbons) = lower boiling point – larger mass = higher boiling point – increase branching = lower boiling point
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Alkanes
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– alkanes are saturated Hydrocarbons – only single bonds between carbon atoms.(the molecule contains all the H atoms possible for the number of carbon atoms present.) – General Formula: C(n)H(2n+2)
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Haloalkanes
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– are alkanes which one or more hydrogen atoms has been replaced by a halogen atom – fluoro = F -cloro = C – bromo = Br – iodo = I
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Alkenes
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– alkenes are unsaturated hydrocarbons – one or more double bonds between carbon atoms. (less than maximum # of H’s.) – general formula: CnH2n
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Alkynes
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– alkynes are unsaturated hydrocarbons – one or more triple bonds between carbon atoms. (less than maximum # of Hs) – general formula: CnH2n-2
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Cyclic Hydrocarbons
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– forms a ring – i.e. cyclopentane
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Aromatic Hydrocarbons
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– are benzene and benzene-related compounds. -benzene = 6 member ring with alternating double bonds.
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IUPAC
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– International Union of Pure and Applied Chemistry. -developed standard nomenclature
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Alkly Groups
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side chains or -R groups.
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Functional Group
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– an atom or group of atoms in an organic compound that gives it characteristic physical and chemical properties. – a place in the compound where chemical reactions occurs. – for an alkene is the double bond; for the alkyne it is the triple bond – in many organic compound, it contains an oxygen atom
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Alcohols
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– functional group = hydroxyl group – general formula: R-OH – are not bases – fairly soluble in water – boiling point is fairly high; the more OH, the higher the boiling point – OL
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Primary (1°) Alcohol
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-the OH group is attached to a primary carbon (bonded to 1 carbon)
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Secondary (2°)Alcohol
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-the OH group is attached to a secondary carbon (bonded to 2 carbon)
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Tertiary (3°) Alcohol
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-the OH group is attached to a tertiary carbon (bonded to 3 carbon)
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Ether
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– functional group: -C-O-C- – fairly soluble in water – increase branching = lower boiling point – straight chain = higher boiling point – OXY alkane
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Aldehyde
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– general formula: RCHO (found in the end chain) – carbonyl group – low molecular mass = water soluble – AL
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Ketone
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– general formula: RCOR’ – carbonyl group – low molecular mass = water soluble – ONE
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Carboxylic acid
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– general formula: RCOOH – carboxyl group – weak acids – very polar and can hydrogen bond – high solubility and high boiling point – OIC acid
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Esters
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– general formula: RCOOR’ – polar, fairly soluble in water – fairly high boiling point – alkyl -OATE
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Amines
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– general formula: R-NH₂ – amino group – good solubility (polar and can H-bond) – medium to high boiling point – AMINOalkane
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Amides
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– general formula: RCNO
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Isomers
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compounds that have the same molecular formula(same number and type of each element) but differ in the arrangement of atoms.
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Structural Isomers
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– compounds that have the same molecular formula but different structural formulas. – Three types of structural isomers: skeletal, positional, and functional.
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Skeletal Isomers
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differ only in the arrangement of atoms in the carbon skeleton.
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Positional Isomers
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differ in the position of the double bond, triple bond, halogen atom, or functional group.
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Functional Isomers
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– differ in the type of bond or the type of functional group. – names are more dramatically different
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Stereoisomers
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– compounds that have the same molecular formula and a very slightly different arrangement of atoms in the molecule – 2 types: geometrical and optical isomers
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Geometric Isomers
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– result from hindered rotation about a double bond. – hindered does not rotate freely. – Cis isomer: on same side (adjacent) -Trans isomers: on opposite side (across)
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Optical Isomers
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-occur when an organic compound contains an asymmetric carbon atom. -non- superimposable mirror images of each other.
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Asymmetric Carbon
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a carbon atom which has four different atoms or groups atoms attached to it.
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Organic reactions
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– oxidation – addition – substitution – condensation – hydrolysis – neutralization
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Oxidation
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– reaction with oxygen – 1° alcohol → aldehyde + water – 2° alcohol → ketone + water – aldehyde → carboxylic acid – organic compound + xs O₂ →CO₂ + H₂O (complete combustion)
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Addition
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-losing a double or triple bond – alkene + H₂ → alkane – alkene + X₂ → haloalkane – alkene + H₂O →alcohol – alkene + H₂ → alkane – alkene +X₂ → haloalkane
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Substitution
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– it is changing places with halogen – alkane + X₂ → haloaklane + HX – banzene + X₂ → halobenzene + HX
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Condensation
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– two small compounds combine (water is a product) – alcohol + Alcohol → ether + H₂O – carboxylic acid + alcohol → ester + H₂O – carboxylic acid + amine → amide + H₂O
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Hydrolysis
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-opposite of condensation ( large molecule breaks apart with water) – ether + H₂O → 2 alcohols – ester + H₂O → carboxylic acid + alcohol – amide + H₂O → carboxylic acid + amine
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Neutralization
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– acid + base → salt + water

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