Key ideas: In EAS, pi bond is Nu and undergoes addition.
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1 Objective 7. Apply addition and elimination concepts to predict electrophilic aromatic substitution reactions (EAS) of benzene and monosubstituted benzenes. Skills: Draw structure ID structural features and reactive sites (alpha C, beta C, LG, etc.) ID Nu - and E + use curved arrows to show bonds breaking and forming show delocalized electrons with resonance structures. Key ideas: In EAS, pi bond is Nu and undergoes addition. Carbocation intermediate undergoes elimination to form substitution product, not addition product. Some groups activate ring, others deactivate ring.
2 π Bonds are Nucleophiles π Bonds undergo Addition Reactions Simple Alkenes, Conjugated Dienes, and Arenes have π Bonds What is the correct ranking in order of Nu: - strength (reactivity with E + )? a. Arenes > Conjugated Dienes > Simple Alkenes b. Conjugated Dienes > Arenes > Simple Alkenes c. Simple Alkenes > Conjugated Dienes > Arenes Give reasons for your ranking.
3 OChem Objectives: (1) given reactants and reaction conditions ==> predict products. Determine all possible products. Use curved arrows to show bonds breaking and forming. Remember: Keep track of the H s. How do carbocations react?
4 Electrophilic Aromatic Substitution (EAS) Occurs in Ring Aromatic pi bond is a weaker nucleophile than simple pi bond. So, aromatic pi bond needs a stronger electrophile than simple pi bond for a reaction to occur. EAS: Why Substitution and Not Addition?
5 Objective: describe EAS mechanism Alkenes undergo addition but aromatics undergo substitution Conjugated diene is less stable than aromatic
6 From LearnBacon.com
7 Use Electrophilic Aromatic Substitution (EAS) to Replace H with Functional Group Benzene --> monosubstituted benzene --> di-, trisub benzene Substitute NO 2, SO 3 H, X, R, COR for H -R and -COR are Friedel-Crafts rxns. See Klein, p. 870 for limitations.
8 Aromatic pi bonds are poor Nu: - Need a very strong E + See Practice Problems??
9 Problem solving steps: 1. Identify functional group(s) 2. Relate reaction conditions to reaction type Objective: Predict the product or ID the reaction conditions
10 5/2/11, CEN, p. 9 Intramolecular Friedel-Crafts alkylation Lewis acid: triisopropylsilyl cation as a paired with a weakly coordinating carborane anion (compare to AlCl 3 ). The R 3 Si + activates C-F bond (compare to CH 3 Cl). Favored by thermo: Si-F bond is stronger than C-F bond
11 EAS of monosubstituted benzenes: slower faster Experiments show different rates and substitution at different position.
12 EAS of monosubstituted benzenes: faster slower Experiments show different rates and substitution at different position.
13 For substituted (mono or higher) benzene, the Substituent (group) on benzene determines the: position of substitution (ortho, meta, or para) rate of reaction Electron Donating Group Activates π e - in ring Faster reaction Ortho, para director -NHR -OH, -OR, -OCOR -R Electron Withdrawing Group Deactivates π e - in ring Slower reaction Meta director -X (but o, p director) -COR, -CHO, -COOH, -COOR -CN, -NO 2
14 Electron donating groups Activate Ring E.g., OH (see chemagic.com) Electron withdrawing groups Deactivate Ring E.g., Cl (see chemagic.com)
15 Why are electron donating groups ortho, para directors? E.g., R = CH 3 is electron donating and activates ring. Draw resonance structures for each intermediate. Which resonance structures are the most stable?
16 You may expect -OH to be electron withdrawing and deactivating but it is the electron donating and strongly activating. Why? Atoms with l.p. adjacent to ring are electron and. E.g., O in alcohol, ether, ester; N in amine, amide
17 Why are electron withdrawing groups meta directors? Which resonance structures are the most stable? Why? C=O (carbonyl) bonded to ring are e - and. E.g., acid, aldehyde, ketone, ester.
18 1. Identify each group as a ortho, para director or meta director: Cl ortho, para director meta director C 2 H 5 ortho, para director meta director CHO ortho, para director meta director OH ortho, para director meta director NO 2 ortho, para director meta director NH 2 ortho, para director meta director 2. Name one limitation of the Friedel-Crafts alkylation reaction.
19 Halogenation in Drug Design (Klein, Organic Chemistry, p. 863) Identify the reaction conditions. Cl substitution occurs ortho to R group because.
20 Objective: Predict EAS product of monosubstituted benzene
21 EAS to Functionalize Benzene Benzene --> Substituted benzene --> disubstituted benzene
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