Chapter 13. Organic Chemistry-Part 2
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1 Chapter 13 rganic Chemistry-Part 2
2 13.4 Aromatic Compounds
3 Aromatic ydrocarbons Benzene (C66) was discovered in 1825, but a partially correct structure was not proposed until 1865 by August Kekule. The structure consisted of six carbons in a ring joined by alternating single and double bonds. Physical and chemical evidence indicates that benzene behaves as if all the carbon-carbon bonds are identical. ence, the following structural representation is sometimes used:
4 Delocalized Bonding in Benzene Sigma bonding system sp 2 hybrid orbitals Remaining p orbitals Delocalized π bonding
5 Aromatic ydrocarbons-nomenclature 1. Identify the benzene ring in a compound and assign the parent name benzene 2. Attach names and location of substituents. 3. For two or more substituents, number the benzene ring starting with one of the substituents to give the lowest combination of numbers to the substituents. 4. Some important monosubstituted benzenes have common names: C 3 N 2 C C Toluene Phenol Aniline Benzoic Acid Benzaldehyde
6 Aromatic ydrocarbons-nomenclature 5. The prefixes ortho (o), meta (m), and para (p) are often used to indicate the relative positions of two substituents in 1,2-, 1,3-, and 1,4- placement on a benzene ring. Br 1 Br Br 2 1 N 2 Br 1 3 Br N 2 4 1,2-dibromobenzene 1,3-dibromobenzene 1,4-dibromobenzene ortho-dibromobenzene meta-dibromobenzene para-dibromobenzene Br Cl
7 Name the following compounds as substituted benzenes. 15) 16) Cl C 2 C Cl 2 N 2 Br 1-chloro-3-isopropyl benzene 2-bromo-1-chloro-5-ethyl-3-nitro benzene
8 The Benzene Ring in Drug Molecules C 3 C 3 C 3 C C 2 C 3 Aspirin Ibuprofen C 3 C 3 Cinnamedrine Dextromethorphan
9 13.5 Amines
10 Amines - Derivatives of Ammonia N Classification by the number of attached groups N N N ethylamine diethylamine triethylamine a primary amine a secondary amine a tertiary amine
11 Amines - Nomenclature Amines containing simple groups are named with common nomenclature. Simple groups include: Unbranched alkyl groups: methyl, ethyl, propyl, butyl,., decyl Branched 3- and 4-carbon alkyl groups: isopropyl, isobutyl, s-butyl, t-butyl Unsubstituted cycloalkyl groups: cyclohexyl and cyclopentyl C3 N C2 C3 ethylmethylamine N C3 C C3 2º 1º isopropylamine C3 N cyclohexylmethylamine C3 C3 2º 3º N C2C3 ethyldimethylamine
12 Amines - Basic Compounds When dissolved in water, amines generate hydroxide ions. N 4 + R R N + 2 R R=, alkyl, aryl R N + R R + - The product of the reaction is a salt and it is named from the name of the starting amine. C3 N methylamine + 2 C3 N a solution of methylammonium hydroxide
13 Amines - Basic Compounds Ammonia may be reacted with a strong acid to quantitatively yield an amonium salt. N3 + Cl N4Cl ammonia hydrogen ammonium chloride chloride An amine may be reacted with a strong acid to quantitatively yield an amine salt. C3 N methylamine + Cl C3 N Cl- + methylammonium chloride
14 The Amino Group in Drug Molecules
15 Amines - Amine Based Drugs C 2C2 N C 3 Cl R-N + C3 Clphenylephrine hydrochloride NESYNEPRINE 3-(2-(methylamino)ethyl)phenol hydrochloride C 2 C 3 C C 2C2 N C 2 C 3 Cl C C 2 C 2 N C 3 Cl C 3 2 N procaine hydrochloride NVACAINE 2-(diethylamino)ethyl 4-aminobenzoate hydrochloride diphenehydramine hydrochloride BENADRYL 2-(benzhydryloxy)-N,N-dimethylethanamine hydrochloride
16 Biologically Interesting Amines
17 Biologically Interesting Amines
18 13.6 Alcohols and Ethers
19 Alcohols, Ethers, Phenols Structure of Functional Groups C C ALCL
20 Alcohols, Ethers, Phenols Structure of Functional Groups PENL C C C C ETER
21 Alcohols, Ethers, Phenols Structure of Functional Groups The oxygen atom in alcohols, phenols, and ethers is sp 3 hybridized. Two of the sp 3 orbitals are involved in bonding to hydrogen or carbon, and the remaining two contain lone-pair, or non-bonding, electrons. R R R water alcohol ether
22 Alcohols, Ethers, Phenols Structure of Functional Groups In water, the -- bond angle is due to repulsion of the bonding electron pairs by the larger non-bonding electron pairs. In alcohols, phenols, and ethers the corresponding bond angles are closer to the expected tetrahedral due to the replacement of one or both hydrogen atoms by larger carbon atoms.
23 Common Names Propyl alcohol (C3C2C2, propanol)
24 Isomerism in Alcohols 1-propanol 2-propanol
25 Nomenclature of Alcohols 1. Select the longest chain containing the - group as the parent chain; replace the -e with -ol 2. Number the parent chain starting at the end closest to the - group 3. Give the number for the position of the hydroxy group in front of the parent name C 2 C2 C 2 C2 C pentanol C 3 C2 C C2 C 3 3-pentanol C 3 C C 2 C2 C 3 2-pentanol
26 4. Give the names and number of substituents 1 Cl C 3 2 C 4 C 3 C C 3 5 C 3 3-chloro-4-methyl-2-pentanol 5. Cyclic alcohols are named as cycloalkanols 6. If more than one alcohol group is present the terms diol, triol, etc. are used
27 Diols and Triols 1,2-ethanediol 1,2,3-propanetriol
28 Physical Properties of Alcohols-Boiling Points Boiling points increase with molecular weight and decrease with branching. Boiling points are higher than alkanes of similar molecular weight. 3 C 2 C C 2 3 C 2 C C 2 3 C 2 C C 2 3 C 2 C C 2 3 C 2 C C 2 3 C 2 C C 2 3 C 2 C C 2 3 C 2 C C 2 3 C 2 C C 2 3 C 2 C C 2 2 C 2 C C 2 C 2 C 3 2 C 2 C C 2 C 2 C 3 2 C 2 C C 2 C 2 C 3 2 C 2 C C 2 C 2 C 3 2 C 2 C C 2 C 2 C 3 2 C 2 C C 2 C 2 2 C 2 C C 2 C 2 C 2 C 2 2 C 2 C 2 C C 2 C 2 2 C 2 C 2 C C 2 C 2 ctane, boiling point = 126 C Attractive forces between alkane molecules are limited to simple London forces. eptanol, boiling point = 176 C Attractive forces between alcohol molecules include both dispersion forces and relatively strong hydrogen bonding.
29 Physical Properties of Alcohols-Solubility Alcohols are more water soluble than alkanes, but their water solubility is limited by the size of the nonpolar portion of the molecule. Nonpolar, or hydrophobic portions of molecules C 3 Polar, or hydrophilic portions of molecules 3 C C 2 C 2 C 2 C2 C 2 C 2
30 Physical Properties of Alcohols-Solubility C 3 C 3 TE RELATIVELY SMALL ATTRACTIN BETWEEN METANL MLECULES MAKES IT EASY FR WATER T SEPARATE INDIVIDUAL METANL MLECULES FRM EAC TER AND DISSLVE TE ALCL. METANL IS VERY SLUBLE IN WATER. TE RELATIVELY LARGE ATTRACTIN BETWEEN EPTANL MLECULES MAKES IT DIFFICULT FR WATER T SEPARATE INDIVIDUAL EPTANL MLECULES FRM EAC TER AND DISSLVE TE ALCL. EPTANL IS VERY SLIGTLY SLUBLE IN WATER. 3 C 3 C C 2 C 2 C 2 C 2 C2 C 2 C 2 C 2 C 2 C 2 C2 C 2
31 Solubilities of a omologous Series of Alcohols is Water
32 Functional Groups and Physical Properties
33 13.7 Carbonyl-Containing Compounds
34 Structure of the Carbonyl Group The carbonyl group is constructed in the same manner as the carboncarbon double bond, from an sp 2 hybridized carbon atom and an sp 2 hybridized oxygen atom. C The angles between the three bonds involved are approximately 120º.
35 Families Containing the Carbonyl Group Y C Z Family Y Z aldehyde or C ketone C C carboxylic acid or C -- ester or C --C amide or C -N
36 Nomenclature of Carbonyl Compounds Ethanal Propanone Ethanoic Acid Methyl ethanoate Ethanamide
37 Nomenclature of Carbonyl Compounds \\
38 Families Containing the Carbonyl Group
39 Aldehydes and Ketones
40 Common Aldehydes and Ketones C 2 Formaldehyde
41 Physical Properties of Aldehydes and Ketones Summary of Important Secondary Forces Which Contribute to boiling Points Alcohols Secondary Attractive Forces -bonding Dipole-dipole London ydrocarbons Aldehydes and Ketones Amines Increased Boiling Point
42 Physical Properties of Aldehydes and Ketones Boiling Point Alcohols Aldehydes Alkanes I I I I I Molecular Mass
43 Physical Properties of Aldehydes Compound C C C 3 C 3 C 2 C C 3 C 2 C 2 C C C 3 C 2 C 2 C 2 Boiling Point (ºC) Water solubility (g/100 ml 2) -21 very soluble 21 very soluble
44 Physical Properties of Ketones Compound 3 C C C 3 C C 3 C 2 C3 C C 3 C 2 C 2 C3 C C 3 C 2 C 2 C 2 C3 Boiling Point (ºC) Water solubility (g/100 ml 2) 56 very soluble C 3 C 2 C 2 C 2 C 2 C C
45 Carboxylic Acids and Derivatives
46 Polymers Polymer (macromolecule) a very large molecule with high molar mass formed by bonding together a large number of small molecules of low molecular mass. Monomer small molecule that bonds with others like it to form polymers. ligomer molecule that contain a few monomers; the middle ground between small molecules and polymers.
47 Addition Polymerization Monomers are added to the growing chain in such a manner so that all the atoms in the original monomers wind up in the chain. Condensation Polymerization Monomers are joined by removing small molecules from combining units. Each monomer has two reactive ends.
48 Addition Polymerization of Ethylenes verall Reaction: A X A X A X A X A X C=C C=C C=C C=C C=C B Y B Y B Y B Y B Y Acid or initiator A X A X A X A X A X C C C C C C C C C C B Y B Y B Y B Y B Y a polyethylene A X ( C C ) n n = number of individual units B Y
49 Addition Polymers from Ethylenes Monomer Polymer Uses C2 C2 (C2 C2 )n bottles, toys, housewares, wire cable insulation, plastic sheeting ethylene polyethylene C2 C (C2 C )n outdoor carpeting, food packaging appliance housings C3 C3 propylene polypropylene C2 C (C2 C )n styrofoam containers, food packaging hairbrush handles, toys styrene polystyrene
50 Addition Polymers from Ethylenes Monomer Polymer Uses C 2 C (C 2 C ) n home siding, gutters, flooring, garden hose, PVC tubing Cl Cl vinyl chloride polyvinylchloride (PVC) C 2 C (C 2 C ) n acrylic textile fibers CN CN acrylonitrile polyacrylonitrile polyacylonitrile CF2 CF2 tetrafluoroethylene (CF2 CF2 )n polytetrafluoroethylene Teflon, mechanical parts, cookware, chemical resistant gaskets
51 Condensation Polymers Polyesters Polyamides
52 Condensation Reactions Condensation reaction two molecules combining to form a larger molecule and a small molecule (typically water). 3 C C 2 C2 C C 3 3 C C 2 C2 C C butanoic acid + methanol methyl butanoate C 2 C 3 C C2 butanoic acid + N ammonia 3 C C 2 C C2 N butanamide + 2
53 Condensation Reactions are also known by the term Dehydration Synthesis
54 Polyester Synthesis etc. Polyesters
55 Polyamide Synthesis etc. Nylons
56 13.8 Chirality
57 Stereochemistry - Review of Isomerism Isomers Structural Isomers Stereoisomers
58 Stereochemistry - Review of Isomerism Isomers Structural Isomers Stereoisomers Cis-trans Isomers Isomers with chiral centers
59 Stereochemistry - andedness in Everyday bjects We can imagine the mirror image of an object. In some cases, the mirror image and the original object are identical. In some cases, the mirror image and the original object are not identical.
60 Stereochemistry - andedness in rganic Compounds Enantiomers - compounds that have the following characteristics: 1) Molecules of two compounds are mirror images of each other. 2) Molecules of two compounds are nonsuperimposable. The characteristics of enantiomers are often the result of a single chiral carbon atom.
61 Stereochemistry - A Chiral Tetrahedral Carbon 1, 2, 3, and 4 must be different groups. What are different groups?
62 Stereochemistry - Examples of Enantiomers bromochlorofluoromethane
63 Stereochemistry - Examples of Enantiomers L-carvone D-carvone
64 Stereochemistry - Examples of Enantiomers 2-bromobutane
65 Chiral Recognition
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