Vision. Cis-trans isomerism is key to vision. How rods work H 3 C CH 3. Protein opsin. 11-cis-retinal. Opsin. Rhodopsin.
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1 Vision Cis-trans isomerism is key to vision. 3 C C C 3 3 C O C 3 11-cis-retinal Protein opsin 3 C C C 3 3 C N Opsin C 3 Rhodopsin Light photons 3 C N Opsin 3 C C C 3 C 3 ow rods work
2 Geometric Isomers of Cyclic Compounds Important in carbohydrate chemistry. Two substituents on the same side (face) of the ring are cis to each other. 3 C C 3 Cis-1,2-dimethylcyclopropane (bp 37ºC) Two substituents on the opposite side (face) of the ring are trans to each other. 3 C C 3 Trans-1,2-dimethylcyclopropane (bp 28ºC)
3 Chemical Properties of Alkenes Addition reactions to the double bond. Addition of symmetrical reagents. X X X X Addition of unsymmetrical reagents. X Y X Y
4 Addition of Symmetrical Reagents 1. Addition of 2 : ydrogenation Ni catalyst Conversion of alkene to alkane. 2. Addition of alogens: alogenation Cl 2 and Br 2 add rapidly to carbon-carbon double bonds. No catalyst is needed. Cl Cl Cl Cl Br Br Br Br I 2 does not add (unreactive). F 2 reacts explosively.
5 Addition of Unsymmetrical Reagents 1. Addition of Cl. Cl Cl Chloroalkane 2. Addition of Br. Br Br Bromoalkane 3. Addition of conc. 2 SO 4. O O S O O O O S O O Alkyl hydrogen sulfate (very polar) Concentrated sulfuric acid dissolves alkenes.
6 Addition of Unsymmetrical Reagents 4. Addition of 2 O: ydration. O catalyst O Water does not add in the absence of an acid catalyst.
7 Addition of Unsymmetrical Reagents Unsymmetrical reagents add selectively to unsymmetrical double bonds. C 3 C 3 C 2 C C 2 Cl 1-chloro-2-methylbutane C 3 C 3 C 2 C C 2 Cl 2-methyl-1-butene C 3 Unsymmetrical alkene C 3 C 2 C Cl C 2 2-chloro-2-methylbutane (major product) Two possible products Note: The products are constitutional isomers.
8 Markovnikov's Rule When an unsymmetrical reactant of the type G adds to an unsymmetrical alkene, the adds to the carbon atom of the double bond that has the greater number of hydrogens. C 3 C C 3 C 3 catalyst C 2 O C 3 CC 3 2-methyl-1-propene O tert-butanol (major product) C 3 C C 2 2 SO 4 C 3 CC 3 1-propene OSO 3 isopropyl hydrogen sulfate (major product) Note: The chemical basis for Markovnikov's Rule is the mechanism for addition (see later).
9 Markovnikov's Rule Markovnikov's Rule does not apply to symmetrical alkenes. i.e. Symmetrical alkenes do not add G selectively. Cl Cl cyclohexene 1-chlorocyclohexane
10 Chemical Basis of Markovnikov's Rule Mechanism of addition of G to alkenes. 2-methyl-1-propene C 3 C 3 C C 2 Cl 3 o Carbocation 1 o Carbocation C 3 C C 3 C 2 C 3 C C 3 C 2 Cl Cl C 3 C 3 C 3 C C 2 C 3 C C 2 Cl 2-chloro-2-methylpropane (major product) Markovnikov Product Cl 1-chloro-2-methylpropane
11 Chemical Basis of Markovnikov's Rule The more stable carbocation preferentially forms. Order of stability of carbocations: R R C 3 < R C 2 < R C Methyl Carbocation LEAST STABLE 1 o Carbocation 2 o Carbocation < R C R 3 o Carbocation MOST STABLE Alkyl groups stabilize the positive charge on the carbocation by electron donation through the σ-bond.
12 Addition of 2 O to Alkenes Mechanism 2-methyl-1-propene C 3 C 3 C C 2 2 O 3 o Carbocation 1 o Carbocation C 3 C C 3 C 2 C 3 C C 3 C 2 2 O 2 O C 3 C 3 C 3 C C 2 C 3 C C 2 O 2 O 2 C 3 C 3 C 3 C C 2 C 3 C C 2 O tert-butanol (major product) O
13 Aromatic Compounds C 3 O Benzene Toluene Benzaldehyde Naphthalene Anthracene Biphenyl Benzene and structural relatives. Aromatic hydrocarbons are found in coal and petroleum.
14 Benzene C C C C C C Does not undergo usual alkene reactions Reacts with Br 2 to give substitution product NOT addition product Br 2 Br Br Br Br Addition Product Substitution Product
15 Benzene as a relatively small heat of hydrogenation. Compare 2 Pt catalyst hydrog Cyclohexene -118 kj/mol 2 Pt catalyst hydrog Cyclohexadiene -230 kj/mol Expect 2 Pt catalyst hydrog Benzene Actual -356 kj/mol 2 Pt catalyst hydrog Benzene -206 kj/mol
16 Benzene Structure Planar molecule, hexagonal shape. All C-C bonds are same length. All C-C-C bond angles are 120 o. Resonance hybrid of two equivalent forms. All six carbon atoms are sp 2 hybridized. p-orbital on each carbon atom perpindicular to plane of ring.
17 Nomenclature Continued There are also a large number of common (or "trivial") names for arenes which are in common usage. Many of these are acceptable "parents" with regard to nomenclature. When one of these is used as the parent chain, the substituent is position #1, by definition.
18 Carcinogenicity of Benzopyrene O Benzo[a]pyrene O O N Base pair O O O "Ultimate Carcinogen" Partial metabolism of of benzopyrene in in mammals in in series of of enzyme-catalysed steps yields highly reactive carbocation known as as the ultimate carcinogen. Carbocation may alkylate base pairs of of DNA ÍÍcarcinogenicity.
19 Electrophilic Aromatic Substitution Examples of electrophilic aromatic substitution reactions. E E 1. Electrophilic aromatic halogenation. X X 2 X 2. Electrophilic aromatic nitration. NO 2 2 SO 4 NO 3 2 O
20 Electrophilic Aromatic Substitution 3. Electrophilic aromatic sulfonation. 2 SO 4 SO 3 SO 3
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