The Effect of Substituents on Reactivity
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1 The Effect of Substituents on Reactivity Substituents that donate electron density to the benzene ring increase benzene s nucleophilicity and stabilize the carbocation intermediate. Substituents that withdraw electron density to the benzene ring decrease benzene s nucleophilicity and destabilize the carbocation intermediate.
2 Inductive Electron Withdrawal and Donation A substituent more electronegative than a hydrogen withdraws σ electrons inductively from the benzene ring more than a hydrogen will. An alkyl group donates electrons by hyperconjugation.
3 Resonance Electron Donation A lone pair on an atom directly attached to the ring donates electrons by resonance.
4 Resonance Electron Withdrawal An atom directly attached to the ring that is doubly or triply bonded to an electronegative atom withdraws electrons by resonance.
5 Strongly Activating Substituents All the strongly activating substituents donate electrons by resonance. All the strongly activating substituents withdraw electrons inductively. Because the substituents are activating, electron donation by resonance is more significant than inductive electron withdrawal.
6 Moderately Activating Substituents Moderately activating substituents donate electrons by resonance.
7 Moderately Activating Substituents Moderately activating substituents are less effective than strongly activating substituents because they donate electrons in two competing directions.
8 Weakly Activating Substituents Alkyl substituents donate electrons by hyperconjugation. Aryl and CH CHR donate and withdraw electrons by resonance: electron donation is more important.
9 Weakly Deactivating Substituents All the weakly activating substituents donate electrons by resonance. All the weakly activating substituents withdraw electrons inductively. Because the substituents are deactivating, electron withdrawal is more important than electron donation.
10 Moderately Deactivating Substituents All the moderately deactivating substituents withdraw electrons by resonance and withdraw electrons inductively.
11 Strongly Deactivating Substituents All the strongly deactivating substituents (except ammonium ions) withdraw electrons inductively and by resonance. Ammonium ions strongly withdraw electrons inductively.
12
13 The Effect of Substituents on Orientation When an electrophilic aromatic substitution reaction occurs on a substituted benzene, where does the new substituent attach itself?
14 Ortho Para Directors All activating substituents are ortho para directors. Weakly deactivating substituents (halogens) are ortho para directors.
15 Meta Directors All moderately and strongly deactivating substituents are meta directors.
16 Which Carbocation Intermediate is the Most Stable? For substituents that donate electrons by resonance, ortho or para substitution forms a relatively stable resonance contributor.
17 Which Carbocation Intermediate is the Most Stable? For substituents that donate electrons inductively, ortho or para substitution forms a relatively stable resonance contributor.
18 Which Carbocation Intermediate is the Most Stable? For substituents that withdraw electrons, ortho or para substitution forms a relatively unstable resonance contributor.
19 Substituents on the Benzene Ring Affect the pka
20 Substituents on the Benzene Ring Affect the pka of Phenol electron donating groups decrease the acidity (destabilize the conjugate base) electron withdrawing groups increase the acidity (stabilize the conjugate base)
21 Substituents on the Benzene Ring Affect the pka of Benzoic Acid electron donating groups decrease the acidity (destabilize the conjugate base) electron withdrawing groups increase the acidity (stabilize the conjugate base)
22 Substituents on the Benzene Ring Affect the pka of Protonated Aniline electron donating groups decrease the acidity (destabilize the conjugate base) electron withdrawing groups increase the acidity (stabilize the conjugate base)
23 The Ortho Para Ratio The size of a substituent affects the ortho para ratio.
24 Halogenation with a Strongly Activating Group Present halogenation of a ring with a strongly activating substituent does not require a catalyst if a catalyst is used, substitution occurs at all ortho and para positions
25 Friedel Crafts Reactions Do Not Occur with Meta Directors Friedel Crafts reactions are the slowest of the electrophilic aromatic substitution reactions and do not occur if the ring is moderately or strongly deactivated.
26 Anilines Do Not Undergo Friedel Crafts Reactions The lone pair on the amino group forms a complex with the Lewis acid catalyst, which converts the substituent to a meta director.
27 Aniline Must Be Protected in Order to Be Nitrated Aniline cannot be nitrated directly because nitric acid will oxidize an NH 2 group. If the amino group is protected by acetylation, the ring can be nitrated. An acetyl group is removed by acid-catalyzed hydrolysis.
28 Designing a Synthesis two routes for the synthesis of 2-phenylethanol The preferred route depends on the number of steps, the complexity of each reaction, and the overall yield. The first route is preferable.
29 The Order of the Reactions is Important The order of the reactions is important.
30 The Order of the Reactions is Important The acetyl group must be added first because a Friedel Crafts acylation will not occur with a meta director on the ring.
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Background A nucleus with an odd atomic number or an odd mass number has a nuclear spin that can be observed by NMR spectrometers.
NMR Spectroscopy I Reading: Wade chapter, sections -- -7 Study Problems: -, -7 Key oncepts and Skills: Given an structure, determine which protons are equivalent and which are nonequivalent, predict the