!!Unsaturated Hydrocarbons. !!Properties of Alkanes
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1 !Organic Chemistry!Why are there so many organic compounds? (three special properties of carbon)!what is a hydrocarbon?!what are the four classifications of hydrocarbons and how do they differ?!know the names of the first 10 hydrocarbons and how to write the molecular and structural formula.!know the bond angle of a H-C-H bond in an alkane.!valence!what is the valence of an atom, and how is it related to valence electrons?!know the rules of valence for an element and how to determine the valence.!be able to write the structural formula for a molecule using the rules of valence.!isomers!what is the definition of isomer?!know what a straight chain alkane vs. a branched alkane is.!know that the prefix n- is used to signify a "!Free rotation about the C-C bond straight chain. "!BP increases as size (# of C) increases LRSVDS CH110 Molec. Geometry 2 LRSVDS CH110 Molec. Geometry 1!!Unsaturated Hydrocarbons "!What is the definition of saturated and unsaturated? "!Which hydrocarbons contain multiple bonds? Single bonds? "!In which hydrocarbons is the rotation about the C-C bond restricted? "!What does a -ene suffix indicate? An -yne suffix?!!isomers "!What is a structural isomer? "!What is a geometric isomer? "!Which types of hydrocarbons do not have geometric isomers? Which do? Why? "!Give an example of each kind of isomer!!properties of Alkanes "!Flexible
2 !!Reactivity of alkanes "!Relatively inert; takes E to initiate reactions "!Combustion reaction; basis of use as fuels, gives off a lot of energy.!!combustion of hydrocarbons "!Complete combustion (hydrocarbon + xs O 2! CO 2 + H 2 O) "!Incomplete combustion (xs hydrocarbon + O 2! CO + H 2 O; basis of production of lethal CO gas when hydrocarbons burned in a closed space)!!functional Groups (NOT ether, amide, or ester) "!Definition of a functional group "!Know the name of each functional group "!Know the structure of each functional group "!Know how to identify them within a molecule. LRSVDS CH110 Molec. Geometry 3!!Non-Carbonyl Functional Groups "!Alcohol; R-OH where R can t be H, polar, water soluble. "!Amines; R 3 N, weak bases, important physiologically "!Ether; R-O-R where R can t be H, polar, unreactive, used as solvents!!carbonyl Functional Groups "!Aldehyde; RCOH, unreactive, used as solvents "!Ketone; RCOR, unreactive, used as solvents "!Carboxylic Acids; RCOOH, weak acids, sour taste, product of air oxidation of alcohols (acetic acid = vinegar) "!Esters; RCOOR, sweet smelling "!Amides; RCONR, weak bases, essential parts of RNA and DNA LRSVDS CH110 Molec. Geometry 4
3 Chapter 9 part 1: Molecular Geometry Read:!BLB " HW:!BLB 9.16, 17, 22, 23, 25, 27" # Packet 9:1 7" Know: " VSEPR theory" # electron pair (electron domain) geometry" # molecular geometry" molecules with more than one central atom" $molecules with multiple bonds" Which Skill Check Test Bonus Deadline is Approaching?? #! What do Structural Formulas tell us? # What do Lewis structures tell us? # Does Shape influence reactivity? # Predict the shape of the molecule by counting: 1." 2." When is EXAM 2??? LRSVDS CH110 Molec. Geometry 5 LRSVDS CH110 Molec. Geometry 6
4 What Determines the Shape of a Molecule?! Electron pairs each other.! Where should the electron pairs be located in the molecule? Electron Domains! Electron pairs " Electron domains! One lone pair = electron domain! One bond (single, double or triple bond) = electron domain. Valence Shell Electron Pair Repulsion Theory (VSEPR) LRSVDS CH110 Molec. Geometry 7 How many electron domains around A? A.! 3 B.! 4 C.! 5 D.! 6 LRSVDS CH110 Molec. Geometry 8
5 Electron-Domain Geometries Electron-Domain Geometries! Count the number of in the Lewis structure.! The geometry corresponds to that number of electron domains. LRSVDS CH110 Molec. Geometry 9 LRSVDS CH110 Molec. Geometry 10
6 Molecular Geometries! Is the electron-domain geometry always the shape of the molecule? Molecular Geometries Some electron domains have more than one molecular geometry.! What is the molecular geometry defined by? LRSVDS CH110 Molec. Geometry 11 LRSVDS CH110 Molec. Geometry 12
7 Linear Electron Domain Trigonal Planar Electron Domain! In this domain, there is only one molecular geometry: linear.! If there are only two atoms in the molecule, what does the geometry HAVE to be?! Two molecular geometries: $!Trigonal planar, if all the electron domains are. $!Bent, if one of the domains is a. LRSVDS CH110 Molec. Geometry 13 LRSVDS CH110 Molec. Geometry 14
8 Lone Pairs and Bond Angles Multiple Bonds and Bond Angles! Nonbonding pairs are physically larger than bonding pairs.! How does this affect neighboring electron pairs?! Double/triple bonds: $!greater electron density on one side of the central atom $!bond angles involving multiple bonds are, and angles on other side of the molecule are. LRSVDS CH110 Molec. Geometry 15 LRSVDS CH110 Molec. Geometry 16
9 Tetrahedral Electron Domain Trigonal Bipyramidal Electron Domain! Three molecular geometries: $!Tetrahedral, if all are pairs $!Trigonal pyramidal if one is a $!Bent if there are two Lone pairs prefer to be equatorial LRSVDS CH110 Molec. Geometry 17 LRSVDS CH110 Molec. Geometry 18
10 Trigonal Bipyramidal Electron Domain Octahedral Electron Domain Four distinct molecular geometries : $!Trigonal bipyramidal $!Seesaw $!T-shaped $!Linear LRSVDS CH110 Molec. Geometry 19! All positions are equivalent! Two lone pairs go on sides of the molecule! Three molecular geometries: $!Octahedral $!Square pyramidal $!Square planar LRSVDS CH110 Molec. Geometry 20
11 How to determine the shape of a molecule 1." Draw the Lewis structure of the molecule. 2." Determine the electron-pair geometry (EPG: count electron domains: multiple bonds count as one domain). 3." Focus on bonded-electron pairs ONLY to determine the molecular geometry (MG) Examples: COCl 2 PCl 5 BrF 3 Bond Angles Octahedral 90 Tetrahedral Trigonal Planar 120 Linear 180 Determine the approximate bond angles indicated Angle #1 Angle #2 1 LP 2 LP A B C D LRSVDS CH110 Molec. Geometry 21 LRSVDS CH110 Molec. Geometry 22
12 Larger Molecules # Describe geometry around a particular atom Number of electron domains Molecular Shapes: Summary Number of bonded atoms Molecular geometry Example 2 2 linear CO trigonal planar BF bent O tetrahedral CH trigonal pyramidal NH bent H 2 O 5 5 trigonal PCl 5 bipyramidal 5 4 seesaw SF T-shaped BrF linear XeF octahedral SF square pyramidal BrF square planar XeF 4 Geometry around atom LRSVDS CH110 Molec. Geometry 23 LRSVDS CH110 Molec. Geometry 24
13 Practice Problems Practice Problem! Which of the following molecules has four electron domains about the central atom?! The molecular geometry of which molecule is square planar? A.! CO 2 A.! CCl 4 B.! XeF 4 B.! SO 3 C.! PH 3 C.! CHCl 3 D.! XeF 2 D.! SeF 4 LRSVDS CH110 Molec. Geometry 25 LRSVDS CH110 Molec. Geometry 26
14 Practice Problems! The molecular geometry of TeF 3 - is best described as: A.! Trigonal pyramidal B.! Trigonal planar C.! See-saw D.! T-shaped LRSVDS CH110 Molec. Geometry 27
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