Organic Chemistry

Section 10.1 How Alkyl Halides React 361 Chapter 12, the substitution and elimination reactions of compounds with leaving groups ...

362 CHAPTER 10 Substitution Reactions of Alkyl Halides The carbon–halogen bond breaks heterolytically without any assistance fr ...

Table 10.1 Relative Rates of SN2 Reactions for Several Alkyl Halides SN 2 RBr+ Cl− RCl+ Br− CH 3 C CH 3 CH 3 CH 3 Br CH 3 Br CH ...

364 CHAPTER 10 Substitution Reactions of Alkyl Halides a. Back-side attack empty σ antibonding MO filled σ bonding MO b. Front-s ...

Section 10.2 The Mechanism of an SN 2 Reaction 365 >Figure 10.2 The approach of to a methyl halide, a primary alkyl halide, a ...

The carbon at which substitution occurs has inverted its configuration during the course of the reaction, just as an umbrella ha ...

Section 10.3 Factors Affecting SN 2 Reactions 367 The weaker the base, the better it is as a leaving group. 10.3 Factors Affecti ...

368 CHAPTER 10 Substitution Reactions of Alkyl Halides The Nucleophile When we talk about atoms or molecules that have lone-pair ...

Section 10.3 Factors Affecting SN 2 Reactions 369 H C X H H C H C X HH I− transition state H C X H H C H C X HH F− transition st ...

370 CHAPTER 10 Substitution Reactions of Alkyl Halides An aprotic solvent does not contain a hydrogen bonded to either an oxygen ...

Section 10.3 Factors Affecting SN 2 Reactions 371 ethoxide ion tert-butoxide ion Nucleophilicity Is Affected by Steric Effects B ...

372 CHAPTER 10 Substitution Reactions of Alkyl Halides 10.4 The Reversibility of an Reaction Many different kinds of nucleophile ...

Section 10.4 The Reversibility of an SN 2 Reaction 373 (Section 3.7). Le Châtelier’s principlestates that if an equilibrium is d ...

374 CHAPTER 10 Substitution Reactions of Alkyl Halides PROBLEM 8 SOLVED What product is obtained when ethylamine reacts with exc ...

Section 10.5 The Mechanism of an SN 1 Reaction 375 10.5 The Mechanism of an Reaction Given our understanding of reactions, we wo ...

376 CHAPTER 10 Substitution Reactions of Alkyl Halides bromide and water is an reaction, where “S”stands for substitution,“N”sta ...

Section 10.5 The Mechanism of an SN 1 Reaction 377 effect on the rate of the reaction. If you look at the reaction coordinate di ...

378 CHAPTER 10 Substitution Reactions of Alkyl Halides If the nucleophile attacks the side of the carbon from which the leaving ...

Section 10.6 Factors Affecting SN 1 Reactions 379 The Nucleophile The nucleophile reacts with the carbocation that is formed in ...

PROBLEM 15 Arrange the following alkyl halides in order of decreasing reactivity in an reaction: 2-bromopentane, 2-chloropentan ...