By Fredric M. Menger, Leon Mandell
Most common texts in simple natural chemistry require the scholar to memorize dozens of natural reactions. this is often definitely essential to grasp the self-discipline. regrettably, such a lot texts don't emphasize why those reactions take place and, simply as vital, why different reactions that would appear attainable to the coed don't take place. with out this realizing, scholars are inclined to overlook what they've got memorized quickly after the direction is over. it's the function of this booklet to familiarize the coed with the rules governing natural reactivity and to supply a "feel" for natural chemistry that's very unlikely to safe by means of reminiscence on my own. Digesting the tips during this publication will, we are hoping, not just clarify the typical natural reactions but additionally permit the scholar to foretell the prod ucts and by-products of reactions he hasn't ever visible ahead of. certainly, the inventive scholar could even develop into in a position to designing new reactions as will be required in a posh natural synthesis. In bankruptcy 1, we disguise the elemental rules together with bonding, nuclear cost, resonance results, oxidation-reduction, and so on. it's a short dialogue, however it still presents the root for figuring out response mechanisms th~t should be handled afterward. We hugely suggest that this fabric be reviewed and that the v VI PREFACE difficulties be labored on the finish of the bankruptcy. solutions are given to all difficulties. In bankruptcy 2, response mechanisms are offered in an increas ing order of difficulty.
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Additional info for Electronic Interpretation of Organic Chemistry: A Problems-Oriented Text
1. H+ a CH OH 3 The Grignard reaction, one of only three reactions whose discovery merited the Nobel prize, is mechanistically nothing more than addition of a nucleophile to a carbonyl. The nucleophile in this case is a carbanion formed when magnesium metal reacts with an alkyl halide: CH~ Br~: Mg ~ CH 3- + MgBr Actually, the carbanion is not really "free" but instead complexed with the magnesium. , product isolation), the salt is converted into the alcohol: + HX RO- MgBr ~ ROH + MgBrX 55 56 CHAPTER2 SOLVED PROBLEMS The above step is analogous to a neutralization reaction, NaOH + HCI gives HOH + NaCl.
The extra two electrons are undoubtedly retained by one of the bromines as it is converted into bromide ion, but this leaves one of the bromines electron-deficient: Br CH3-~CH2 &r Br+ CH 3-CH=CH 2 Br- Electron-deficient bromine (Br+) is an unstable species, which explains in part why 1,2-dibromides do not spontaneously form 51 52 CHAPTER2 SOLVED PROBLEMS alkenes. Thus far our analysis of the debromination has ignored an important component of the reaction, namely, metallic zinc. Br CH 3 -C~CH2 ~ CH 3CH=CH &r 2 + ZnBr2 8.
F. g. h. neither oxidizing agent oxidizing agent reducing agent neither neither neither reducing agent 11. a. b. c. d. e. second second fIrst first second 12. a. b. c. d. fIrst fIrst second second Note: The amide in problem (a) protonates (in concentrated H 2 S0 4 ) on the oxygen to give a resonance-stabilized cation. CHAPTER 1 ANSWERS 13. 00- 00 00 00° ~ ~~I ° ° ~ 14. No. There is no way of "pushing" the negative charge on the phenolate oxygen onto the oxygen of the ketones. 45 CHAPTER 2 Solved Problems in Organic Reaction Mechanisms 1.