Organic Chemistry

Problems 621 Purine is a heterocyclic compound with four nitrogen atoms. a. Which nitrogen is most apt to be protonated? b. Whi ...

622 16 Reactions of Substituted Benzenes Chlorobenzene meta-Bromobenzoic acid ortho-Chloronitrobenzene para-Iodobenzenesulfonic ...

(known as dioxin) is a contaminant formed during the manufacture of Agent Orange. TCDD has been implicated as the causative agen ...

624 CHAPTER 16 Reactions of Substituted Benzenes 16.1 Nomenclature of Disubstituted and Polysubstituted Benzenes Disubstituted B ...

PROBLEM 1 Name the following compounds: PROBLEM 2 Draw structures of the following compounds: a.para-toluidine c.para-xylene b ...

626 CHAPTER 16 Reactions of Substituted Benzenes 16.2 Reactions of Substituents on Benzene In Chapter 15, you learned how to pre ...

Section 16.2 Reactions of Substituents on Benzene 627 Remember that halo-substituted alkyl groups can also undergo E2 and E1 rea ...

628 CHAPTER 16 Reactions of Substituted Benzenes If the alkyl group lacks a benzylic hydrogen, the oxidation reaction will not o ...

It is possible to selectively reduce just one of two nitro groups. PROBLEM 5 Give the product of each of the following reaction ...

630 CHAPTER 16 Reactions of Substituted Benzenes Electron-donating substituents increase the reactivity of the benzene ring towa ...

If a substituent is attached to the benzene ring by an atom that is doubly or triply bonded to a more electronegative atom, the ...

632 CHAPTER 16 Reactions of Substituted Benzenes Table 16.1 The Effects of Substituents on the Reactivity of a Benzene Ring Towa ...

Section 16.3 The Effect of Substituents on Reactivity 633 These substituents are less effective at donating electrons into the r ...

The moderately deactivating substituentsall have carbonyl groups directly attached to the benzene ring. Carbonyl groups withdraw ...

Section 16.4 The Effect of Substituents on Orientation 635 3-D Molecules: Toluene; Bromobenzene All activating substituents are ...

636 CHAPTER 16 Reactions of Substituted Benzenes Y H Y H Y H Y H Y H Y H H Y H Y H Y CH 3 CH 3 + Y+ + CH 3 + CH 3 + CH 3 + CH 3 ...

Section 16.4 The Effect of Substituents on Orientation 637 anisole Y H Y H Y H Y H Y H Y H Y H H Y H Y H Y H Y OCH 3 + Y+ OCH 3 ...

638 CHAPTER 16 Reactions of Substituted Benzenes All substituents that donate electrons into the ring either inductively or by r ...

Section 16.5 The Effect of Substituents on pKa 639 The more deactivating (electron withdrawing) the substituent, the more it inc ...

PROBLEM-SOLVING STRATEGY The para-nitroanilinium ion is units more acidic than the anilinium ion ( versus 4.58), but para-nitrob ...