Chem 263 Oct. 4, 2016
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1 Chem 263 ct. 4, 2016 ow to determine position and reactivity: Examples The strongest donating group wins: S S S ,4,6-trinitrophenol picric acid This reactivity can be explained by the following resonance forms: Meta-director example: 3 2 S 4 This reactivity can be explained by the following resonance forms:
2 The electrophile is positive and reacts at sites that are not positive (ortho para) but at those that are more negative (meta) as shown below A Different Example : S In this reaction, chlorobenzene has a chloro (-) group attached on the benzene ring. When we perform nitration, only ortho and para substitution occurs. The chloro group is an electron withdrawing group inductively, however, the lone pairs of electrons are conjugated to the benzene ring through resonance as an electron donating group. As a result, resonance beats inductive effect, which gives ortho and para substitution products. owever, chlorbenze is less reactive than benzene
3 Example: Acetophenone is meta directing 3 2 S Al 3 When the electrophile attacks, it avoids the partial positive charges on the ortho and para positions: Aromatic compounds with an alkyl chain are considered inductively donating (weak) and will direct substitution to the ortho or para positions. Example: R
4 Br AlBr 3 Al 4 This cation is stabilized by resonance as well as the donation of electrons from the t-bu group via induction effects (shown by the red arrow) The reaction occurs at the para position instead of the ortho position due to sterics. otice how the order that reactions are done affect the following two examples: 3 Al 3 2 S S 4 2 Al 3 2 The products of the above two reactions are structural (or constitutional) isomers.
5 Aromatic compounds that have an electron-withdrawing group attached but that do not fall into the above categories (e.g. C 3 ) are inductively withdrawing and direct substitution to the meta position. Example: 3 2 If ortho: 2 S 4 2 disfavored (not observed) 2 2 -C 3 is electron-withdrawing and does not want to withdraw electrons from a carbon that is already positively-charged. Multiple Substitution If there is more than one group on an aromatic ring, electrophilic aromatic substitution is controlled by the strongest donating group. An example is the dialkylation of methoxybenzene with methyl iodide by riedel-crafts alkylation. Since the methoxy group is an electron-donating group (resonance donator), it will direct the first alkylation to the ortho and para positions. The second alkylation is also directed to the ortho and para positions relative to the methoxy group because it is a stronger director (resonance donator) than the methyl group (inductive donator). The second alkylation will go ortho to the methoxy rather than ortho to the methyl.
6 resonance from methoxy C 3 I inductive from methyl inductive from methyl C 3 I Al 3 resonance from methoxy Al 3 Similarly, nitration occurs at the ortho position for the following example: C 3 C S 4 C 3 C 3 In the following case the nitro group is an electron-withdrawing group, so the methyl group is the strongest donating group and takes precedence in directing where the acetyl group will go. C 3 C 3 C 3 3 C B 3 In this last example, the position between the two meta substituents is too sterically hindered. Therefore, substitution in that position is not observed. ollow-up: ow do you synthesize the starting material in the previous reaction? Answer: 3 C 3 C 3 2 S 4 2 Al 3 2 If alkylation was done first, followed by nitration, the meta-substituted aromatic compound could not be obtained, since the methyl group is an ortho/para-directing group.
7 ow to determine position and reactivity: 6 & 5 membered rings are favoured S 2 thionyl chloride + (this reaction will be covered later in the course) phthalic anhydride Al 3 anthraquinone After the first two reactions, the substituent (a ketone) would normally direct the second acylation to the meta position as a resonance withdrawer. This does not occur, as this would produce a very strained structure. In this example, the second acylation goes to the ortho position to relieve the strain to produce anthraquinone. 6-rings are favoured, as are intramolecular reactions. Synthesis Example: The sequence of steps is critical ow to make versalide, shown below, from benzene?
8 The answer is below. Be able to rationalize this sequence. Al 3 Al 3 Al 3 If you start to add ethyl group first, polyalkylation happens: C 3 C 2 Al 3 Alkylation must also be last because the acetyl group will direct to the meta position. Reaction of Side Chains of Aromatic Compounds: 1) Alkyl Side Chain xidation 2) emmensen Reduction 3) itro Reduction 4) Amino Diazotization 5) Diazo Replacement + Coupling Alkyl Side Chain xidation Reaction
9 If the carbon directly attached to the aromatic ring has > 1 hydrogen attached to it, it can be oxidized to the corresponding carboxylic acid using hot aqueous potassium permanganate (KMn 4 ) as shown below. Carbon dioxide (C 2 ) is one of the side products C R' R KMn 4 2, KMn 4! propyl benzene KMn 4 KMn 4 + C 2 no rxn (no adjacent 's to the aromatic ring) KMn 4 2, More examples of alkyl side chain oxidation: KMn 4
10 KMn 4 The above answer is accepted as it fits the rule given, but in reality, the methyl group of the ketone is also oxidized to a carboxylic acid (special case) KMn 4 Another example KMn 4 C 2 tetralin C 2 (phthalic acid)
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