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UNIT 6. Theories of Covalent Bonding and Intro to Organic Chemistry: Nomenclature of Alkenes, Alkynes, Alcohols. Structural Isomers Have the Same Molecular Formula. Draw the line angle structure of:.
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UNIT 6 Theories of Covalent Bonding and Intro to Organic Chemistry: Nomenclature of Alkenes, Alkynes, Alcohols
Structural Isomers Have the Same Molecular Formula Draw the line angle structure of: The molecular formula of this compound is C8H18. Draw three more structural isomers of octane.
Valence Bond Descriptions .. .. .. :O = S = O: What orbitals overlap to form each of the bonds in SO2? • The S-O sigma bond in each double bond is formed by the overlap of an O sp2 hybrid orbital with a S sp2 hybrid orbital. • Each S-O pi bond is formed by the overlap of the S 3pz orbital with the O 2pz orbital. • Two sp2orbitals on each of the O’s and one sp2 orbital on the S are not involved in any bond.
Nomenclature of Alkenes • Number the C chain from the end that brings you to the double bond sooner, then use the alkane naming rules and -ene. IUPAC (common) H2C=CH2ethene (ethylene) H2C=CH-CH3propene (propylene) • Planar geometry around the double bond • 120° bond angles to the C atoms in the double bond
Nomenclature of Alkenes cis-but-2-ene bp = 4°C methylpropene bp = - 7°C geometric isomers but-1-ene bp = -6°C What are the bond angles? All four are structural isomers. trans-but-2-ene bp = 1°C
Nomenclature of Alkenes Name this alkene. 6,6-dichloro-5-ethyl-4-methylhept-1-ene Give a VB description of the C-Cl bond. Draw the line angle structure for 1-chloro-3-methyl-1,3-butadiene
Alkynes • Contain at least one C≡C bond. Alkynes are unsaturated molecules. • The two π bonds make the geometry through the triple bond linear. • The triple bond is highly reactive, so alkynes are not found widely in nature, though they are used as intermediates in industrial processes.
Nomenclature of Alkynes • Number the C chain from the end that brings you to the triple bond sooner, then use the alkane naming rules and -yne. IUPAC (common) HC≡CH ethyne (acetylene) HC≡C-CH3propyne • Linear geometry around the triple bond • 180° bond angles to the C atoms in the triple bond
Alkynes Draw the condensed structural formula and line angle structure for 4-methylpent-2-yne. CH3 - C≡ C - CH - CH3 | CH3 CH3C≡CCH(CH3)2 * What is the hybridization on the starred C? What is the geometry? Give a VB description of one of the C-C pi bonds.
Alcohols • Contain the -OH (hydroxyl) group. • Alcohols are NOT bases. In fact, some can be acidic (phenol). • Can be soluble in polar solvents such as water (hydrocarbons are not soluble in water). • Primary (1°) alcohols: R – CH2 - OH • Secondary (2°) alcohols: R - CH - R' | OH • Tertiary (3°) alcohols: R″ | R - C - R' | OH R,R',R″ designate the rest of the molecule. R represents an alkyl group.
Nomenclature of Alcohols Number the C chain from the end that brings us to the -OH group sooner, then use the alkane naming rules and -ol. 1° alcoholsIUPAC (common) CH3CH2OH ethanol (ethyl alcohol) CH3CH2CH2OH propan-1-ol (n-propyl alcohol) or 1-propanol *CH3OH *Methanol is not primary, it’s a methyl alcohol.
Nomenclature of Alcohols Number the C chain from the end that brings us to the -OH group sooner, then use the alkane naming rules and -ol. 2° alcoholsIUPAC (common) CH3CHCH3propan-2-ol (isopropyl alcohol) | or 2-propanol OH CH3CHCH2CH3butan-2-ol or 2-butanol | OH
Nomenclature of Alcohols isopropyl alcohol IUPAC: propan-2-ol or 2-propanol t-butyl alcohol IUPAC: methylpropan-2-ol ethylene glycol IUPAC: ethane-1,2-diol Which are primary? Secondary? Tertiary?
Nomenclature of Alcohols 1°? 2°? 3°? Give the IUPAC name of each. Give a VB description of one of the O-H bonds.
Nomenclature of Alcohols propylene glycol glycerine, glycerol IUPAC:propane-1,2,3-triol phenol IUPAC: phenol Draw the line angle structure for 2-methyl-3-butyn-2-ol
Nomenclature of Alcohols IUPAC:10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol What is the H-C-C bond angle for either of the “dashed” H’s?
Functional Groups - Review alcohol ether alkene R = alkyl group - X halide alkyne - C≡N amine (1°) nitrile
Functional Groups - Review aldehyde carboxylic acid amide ketone ester aromatic ring
Functional Groups Circle and label each functional group. fructose threonine γ-butyrolactone (GBL) acetaminophen