Organic Chemistry

11.1 The E2 Reaction Just as there are two important nucleophilic substitution reactions— and are two important elimination reac ...

402 CHAPTER 11 Elimination Reactions of Alkyl Halides • Competition Between Substitution and Elimination In an E2 reaction of an ...

Section 11.2 The Regioselectivity of the E2 Reaction 403 Progress of the reaction Free energy 1- butene + CH 3 OH + Br– 2- buten ...

404 CHAPTER 11 Elimination Reactions of Alkyl Halides • Competition Between Substitution and Elimination Alexander M. Zaitsev (1 ...

CCH 3 RO− CH 3 Base More substituted product Less substituted product CH 3 Br CH 3 CH + CH 3 CH 2 O− 79% 21% 27% 73% 19% 81% 8% ...

406 CHAPTER 11 Elimination Reactions of Alkyl Halides • Competition Between Substitution and Elimination product obtained from t ...

Section 11.2 The Regioselectivity of the E2 Reaction 407 3-D Molecules: Methyl anion; Ethyl anion; sec-Propyl anion; tert-Butyl ...

in which the developing negative charge is on a secondary carbon. Because the transition state leading to 1-pentene is more stab ...

Section 11.3 The E1 Reaction 409 Movie: E1 Elimination An E1 reaction is a first-order elimination reaction because the rate of ...

Because the first step is the rate-determining step, the rate of an E1 reaction de- pends on both the ease with which the carboc ...

secondary alkyl halides, which, in turn, are more reactive than primary alkyl halides in both E1 and E2 reactions (Section 11.2) ...

PROBLEM-SOLVING STRATEGY Propose a mechanism for the following reaction: Because the given reagent is an acid, start by protonat ...

Section 11.5 Stereochemistry of E2 and E1 Reactions 413 PROBLEM 8 For each of the following reactions, (1) indicate whether eli ...

414 CHAPTER 11 Elimination Reactions of Alkyl Halides • Competition Between Substitution and Elimination Sawhorse projections re ...

Section 11.5 Stereochemistry of E2 and E1 Reactions 415 Progress of the reaction Free energy (Z)-2-pentene (E)-2-pentene 2- brom ...

416 CHAPTER 11 Elimination Reactions of Alkyl Halides • Competition Between Substitution and Elimination When only one hydrogen ...

Section 11.6 Elimination from Cyclic Compounds 417 In contrast, we just saw that an E2 reaction forms both the Eand Zproducts on ...

418 CHAPTER 11 Elimination Reactions of Alkyl Halides • Competition Between Substitution and Elimination 3-D Molecules: Axial ch ...

d. c. Stamps issued in honor of English Nobel laureates: (a) Sir Derek Barton for conformational analysis, 1969; (b) Sir Walter ...

420 CHAPTER 11 Elimination Reactions of Alkyl Halides • Competition Between Substitution and Elimination Because a carbocation i ...