1 che 102 chap 19 chapter 19 organic chemistry: saturated hydrocarbons
TRANSCRIPT
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CHE 102 Chap 191
Chapter 19
Organic Chemistry: Saturated Hydrocarbons
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CHE 102 Chap 192
Success!
• First two weeks is key to the 1st half of the semester• Need to build a framework for what we will cover
– Naming and Drawing molecules
– Physical properties (as a function of structure)
– Reactions
– Each category above is about 25% of each exam, the last 25% is miscellaneous concepts.
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CHE 102 Chap 193
Organic Chemistry
• Study of compounds containing C, H, O, N (other trace elements – P, S, Halogens)
• Covalent Molecules
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CHE 102 Chap 194
Lewis Structures (Review Ch 11)
• # bonds formed by C, H, O, N, Halogens
• Single, double, triple bonds
• Molecular geometry
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CHE 102 Chap 195
Hybridization (Review Ch 10)
• Lewis Models Fail!• Required to explain differences in bond strength and
length
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CHE 102 Chap 196
Hybrid Orbitals
• s + 3p -> sp3
• Sigma Bonds () = single bonds
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CHE 102 Chap 197
Representing Organic Molecules
• Molecular Formula• Structural Formula
– Lewis structures• With electrons
• With bonds
• Condensed Formula– Assumes some knowledge of Lewis Structures/Bonding
• Line Models• R-groups
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CHE 102 Chap 198
Functional Groups
• Organic compounds with similar structures are grouped into classes as shown in Table 19.1.
• The members of each class of compounds contain a characteristic atom or group of atoms called a Functional Group.
– is part of a larger molecule.– is composed of an atom or group of atoms that have characteristic
chemical behavior.– Chemically, a given functional group behaves in nearly the same
way in every molecule it’s part of.
• MEMORIZE the General Formula’s in Table 19.1
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CHE 102 Chap 199
Functional Groups
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CHE 102 Chap 1910
Functional Groups
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CHE 102 Chap 1911
Functional Groups
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CHE 102 Chap 1912
IUPAC System for Naming Organic Compounds
• The method recommended by the International Union of Pure and Applied Chemistry is systematic, generally unambiguous, and internationally accepted.
• Some trivial or common names are still used.
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CHE 102 Chap 1913
Naming Alkanes
1. Select the longest chain = Main chain– All other chains = side chains
2. Number the carbon atoms in the parent carbon chain from one end to the other, starting at the end closest to the first carbon atom that has a branch chain.
3. Name each branch-chain alkyl group and designate its position on the parent carbon by a number.
• Multiple side groups use (di, tri, tetra, penta…)
• Name multiple different groups alphabetically
• Ties go in alphabetical order
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CHE 102 Chap 1914
Naming the Main Chain
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CHE 102 Chap 1915
Side Group NamesParent name, change –ane to -yl
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CHE 102 Chap 1916
Special Side Groups
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CHE 102 Chap 1917
Don’t Get Confused!
• The longest chain isn’t always straight• The longest chain isn’t always left to right, it can go
up/down or curve all around• Chain numbers don’t always go left to right• Always maximize the number of side chains• Ties go in alphabetical order
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CHE 102 Chap 1918
Drawing Alkanes
1. Draw the main chain
2. Number the main chain, attach side chains.
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CHE 102 Chap 1919
Alkyl halides or Haloalkanes
• Name like regular alkanes• Halogen = side chain
– F = fluoro
– Cl = chloro
– Br = bromo
– I = iodo
• The longest chain MUST contain the halogen.
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CHE 102 Chap 1920
Isomers
• Compounds with:– Same Formula
– Different Structure
• The various individual compounds are called isomers.– e.g. There are two isomers of C4H10.
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CHE 102 Chap 1921
Example of IsomersIt is possible to write two structural formulas corresponding to the molecular formula C4H10:
C C C
HH
H
H
H
H
C
H
H
H
H
butane or n-butanebp = -0.5 Cmp = -138.3 C
C C C
HH
H
H
C
H H
isobutanebp = -11.7 Cmp = -159.5 C
H
H
H
H
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CHE 102 Chap 1922
How to Draw Isomers
• Start with parent compound:– Rip a carbon off, and attach it to the main chain (but not in
an end position)
– Move carbon along positions in chain• Only do ½ the molecule (otherwise its symmetrical/identical)
• Name molecules to double check you don’t duplicate them
– Rip off another carbon and repeat above until you can make no new structures.
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CHE 102 Chap 1923
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CHE 102 Chap 1924
Cycloalkanes
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CHE 102 Chap 1925
Naming Cycloalkanes
• Main Chain– Just stick “cyclo” in front of it
• Side Chains– Single group (numbers not needed)
– 2+ Groups, number clockwise or counter clockwise to give the lowest set of numbers possible
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CHE 102 Chap 1926
Hydrocarbons
Contain only C and H– aliphatic (do not contain benzene ring)
• alkanes, cycloalkanes
• (Ch 20) alkenes, alkynes
– aromatic (contain a benzene ring)• Ch 20
– An organic compound is classified as saturated if it contains only single bonds.
– An organic compound is classified as unsaturated if the molecules possess one or more multiple carbon-carbon bonds.
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CHE 102 Chap 1927
Physical Properties
• Alkane molecules are non-polar.– Carbon-carbon bonds are non-polar, since they are between
like atoms.
– Carbon-hydrogen bonds are only slightly polar.
– Low polarity =>low boiling points
– Boiling point is a function of mass
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CHE 102 Chap 1928
Physical Properties
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CHE 102 Chap 1929
Reactions Involving Carbon (General)
• General– Oxidation/Reduction
– Substitution
– Elimination
– Addition
• Specific to Alkanes– Halogenation
– Dehydrogenation
– Combustion
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CHE 102 Chap 1930
Recognizing Reactions
• Examine the products and reactants (classes)– Ex: Alkane + Halogen -> Alkyl Halide
– Ex: Alkane + O2 -> CO2 + H2O + Energy
• Examine the catalysts or reaction conditions
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CHE 102 Chap 1931
Oxidation
When carbon atoms are oxidized, they often form additional bonds to oxygen.
H
CH H
H
+ 2 O2 O C O + 2H2O
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CHE 102 Chap 1932
Reduction
When carbon atoms are reduced, they often form additional bonds to
hydrogen.H
CH OH
H
+ 3 H2O C O + H2O
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CHE 102 Chap 1933
Substitution Reaction
If, in a reaction, one atom in a moleculeis exchanged by another atom or group ofatoms, a substitution reaction has takenplace.
H
CH H
H
+ Br2
H
CH Br
H
+ HBr
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CHE 102 Chap 1934
Elimination Reaction
• An elimination reaction is a reaction in which a single reactant is split into two products, and one of the products is eliminated.
• Elimination reactions form multiple bonds.H
CC Br
H
+ HBrH
H
H
H
CC
H
H
H
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CHE 102 Chap 1935
Addition Reaction
• Two reactants adding together to form a single product is called an addition reaction.
• An addition reaction can be thought of as the reverse of an elimination.
H
CC Br
H
+ HBr H
H
H
H
CC
H
H
H
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CHE 102 Chap 1936
Reactions of Alkanes
• Combustion• Halogenation
– a substitution reaction
• Dehydrogenation – an elimination reaction
• Cracking – breaking up large molecules to form smaller ones
• Isomerization – rearrangement of molecular structures
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CHE 102 Chap 1937
Combustion
Alkane + O2 CO2 + H2O + Heat/Energy
2 C3H6 + 9 O2 6 CO2 + 6 H2O + Heat/Energy
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CHE 102 Chap 1938
Halogenation
CH3CH3 + Cl2 CH3CH2Cl + HCl
Alkane + X2 (F, Cl, Br, I) Alkyl Halide + HX
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CHE 102 Chap 1939
CH3CH2CH3 CH3CH=CH2 + H2
Dehydrogenation
Heat
Alkane Alkene + H2
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CHE 102 Chap 1940
Isomerization
CH3CH2CH2CH2CH3
catalyst,pressure,heat CH3CH2CHCH3
CH3
Cracking
C16H34 C8H18 + C8H16