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Chapter 1 Saturated Hydrocarbons Organic chemistry is involved with the protective coating on this apple.
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2 Organic chemistry is the study of covalent compounds ctg. carbon….. …… excluding the binary carbon compounds from group VIA.. What is organic chemistry ?
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3 Practice: Classify the follow compounds as organic or inorganic compounds SOCl 2 CH 3 NH 2 CoCO 3
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4 Organic compounds include drugs, fuels, toiletries, plastics, and fabrics. Lipstick is made of organic molecules. Cosmetics and perfumes contain organic compounds.
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12 | 5 Oil is a mixture of many different organic compounds.
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6 Gasoline is a mixture of many different organic compounds but mainly isooctane and heptane.
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Isoctane and heptane are hydrocarbons…..…let’s look how they are classified.
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Classification of Hydrocarbons
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Alkanes
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Alkanes are molecules that contain only C-C and C-H single bonds. Alkanes are acyclic while cycloalkanes are cyclic.
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Alkanes have the formula C n H 2n+2 (where n = an integer)
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Cycloalkanes have the formula C n H 2n
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Practice Exercise: Circle each molecule that can be classified as an alkane
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Types of Formulas
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Three major categories are used to represent organic cmpds 1.Molecular ( number and type of atoms) e.g. C 3 H 8 is propane ) 2.Structural ( wide variation in use) (a) Lewis structure ( or expanded) (b) Condensed (c) Line-angle (or skeletal, not C-C-C however)
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3. Models ( used to represent cmpds on paper or in 3D space) (a) Ball and stick (all atoms and all bonds in 3D) (b) Space –filling (only atoms are shown in 3D) (a) Dash and wedge ( all atoms and all bonds on a 2D surface)
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Practice Exercise: Change the line-angle formula to a condensed formula and a molecular formula. See problem 12.35 ( 1.49)
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Review of Line Angle Structures
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See practice problem in class
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Naming Alkanes
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How to Name Alkanes (C n H 2n+2 )
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Before you learn to name alkanes you must…….
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Learn these parent names
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Identifying the Longest Chain
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What is the name of this alkane?
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Identify the longest chain and then name it
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Naming the Substituents
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Groups along C backbone are called substituents Alkane substituents are called alkyl groups Alkyl groups are the parent RH (alkane) minus a H atom Naming Substituents (Alkyl Groups)
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Examples of Alkyl Groups
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You must know these alkyl group names and the common abbreviations.. methyl (Me) ethyl ( Et) propyl( Pr) isopropyl(i-Pr)
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What is the name of this alkane?
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Name the alkyl groups on the longest chain. Now, indicate the location of the substituent on the chain (the locant).
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methyl + methyl = dimethyl ethyl 2 + 5 + 6 = 9 (left to right) 2 + 3 + 7 = 10 ( right to left )
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methyl + methyl = 2, 6-dimethyl 5-ethyl- ( note e comes before m) 2 + 5 + 6 = 13 (left to right sum is lower) 3 + 4 + 7 = 14 ( right to left )
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5-ethyl-2, 6-dimethyloctane
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Let’s do a practice problem!
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Name this compound
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Draw the line-angle formula for this compound 3-ethyl-2-methylhexane
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Naming Cycloalkanes
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You must know the four cycloalkanes shown in the next slide
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Cyclopentane Cyclohexane Cyclopropane Cyclobutane Practice: Match the name with the structure.
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47 Naming Cycloalkanes When naming monosubstituted cycloalkanes: 1. Name the substituent 2. Name the parent cycloalkane
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48 For example : These are identical molecules that are named this way: methyl + cyclohexane = methylcyclohexane
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49 Practice : Give the IUPAC name for each compound.
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Isomers
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Isomers are two or more molecules with the same molecular formula but ….. …differ in how the atoms are connected or …… how the atoms are positioned in space.
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Are these isomers?
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Yes they are isomers. What type of isomers are they?
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Constitutional Isomers
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Examples of Constitutional Isomers ( Alkanes) 2-methylpentane3-methylpentane
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Example of Constitutional Isomers (RX) 1-bromopropane2-bromopropane
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Examples of Constitutional Isomers ( Alkenes) 1-pentene 2-pentene
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Stereoisomers (Alkane Conformers)
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Conformers are stereoisomers formed by C-C bond rotation or by changes in certain ring containing molecules.
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In general the major conformers of ethane are either eclipsed or staggered.
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Stereoisomers (Cis-Trans)
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Example of Ring Cis-Trans Isomers cis-1,2-dibromocyclohexane trans-1,2-dibromocyclohexane
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Example of Alkene Cis-Trans Isomers cis-1,2-dibromoethene trans-1,2-dibromoethene
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Classification of Carbon Atoms
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A carbon atom in an organic compound can be classified by the number of carbon atoms bonded to it. A carbon atom is either: a.primary (1°) b.secondary (2°) c.tertiary (3°), or d.quaternary (4°)
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Physical Properties of Hydrocarbons (saturated and unsaturated)
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Why is oil insoluble in water? Why does it float on top of water ?
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Property Description Solubility Density m.p./ b.p. Polarity Table of Properties for Hydrocarbons
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Property Description SolubilitySoluble in organic solvents like ether, alcohol, acetone Insoluble in water Density m.p./ b.p. Polarity Table of Properties for Hydrocarbons
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Property Description SolubilitySoluble in organic solvents like ether, alcohol, acetone Insoluble in water DensityLess than 0.8 g/mL ; will float above water m.p./ b.p. Polarity Table of Properties for Hydrocarbons
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Property Description SolubilitySoluble in organic solvents like ether, alcohol, acetone Insoluble in water DensityLess than 0.8 g/mL ; will float above water m.p./ b.p.Increases as the number of C atoms increase PolarityNonpolar Table of Properties for Hydrocarbons
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Change in b.p. of hydrocarbons as a function of structure
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Alkane Reactions
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1. Combustion
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2. Halogenation (X atom replaces H atom; only Cl and Br are used) CH 3 Cl + HCl
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