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Organomagnesium compounds
The interaction of alkyl halide with Mg metal in a suitable ether solvent is the common method for the synthesis of the Grignard reagent.
Hydrolysis Grignard Reactions and Reduction
Organomagnesium halides are Grignard reagents. Francois Auguste Victor Grignard, a French chemist who received the Nobel Prize in Chemistry in 1912, created these highly useful reagents.
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- Identify the missing reagents a-f in the following scheme:Identify the reagents represented by the letters a-e in the following scheme:Salsolinol is a naturally occurring compound found in bananas,chocolate, and several foods derived from plant sources. Salsolinol isalso formed in the body when acetaldehyde, an oxidation product of theethanol ingested in an alcoholic beverage, reacts with dopamine, aneurotransmitter. Draw a stepwise mechanism for the formation ofsalsolinol in the following reaction.
- Draw a stepwise mechanism for the attached reaction that illustrateshow two substitution products are formed. Explain why 1-bromohex-2-ene reacts rapidly with a weak nucleophile (CH3OH) under SN1 reactionconditions, even though it is a 1 ° alkyl halide.For the following reaction scheme, match the correct reagent to each reaction (A, B, C, D and E).Devise a stepwise mechanism for the following reaction. (Hint: The mechanism begins with the conjugate addition of −OH.)
- Sulfur ylides, like the phosphorus ylides of Chapter 21, are useful intermediates in organic synthesis. Methyl trans-chrysanthemate, an intermediate in the synthesis of the insecticide pyrethrin I (Section 26.4), can be prepared from diene A and a sulfur ylide. Draw a stepwise mechanism for this reaction.Addition of HCl to alkene X forms two alkyl halides Y and Z. (A) Label Y and Z as a kinetic or thermodynamic product and explain why. (B) Explain why the addition of HCl occurs at the exocyclic C=C, rather than the other C=CBromoetherication, the addition of the elements of Br and OR to a double bond, is a common method for constructing rings containing oxygen atoms. This reaction has been used in the synthesis of the polyether antibiotic monensin (Problem 21.37). Draw a stepwise mechanism for the following intramolecular bromoetherication reaction.
- One step in the synthesis of the antihistamine fexofenadine (Section 23.5) involves acid-catalyzed hydration of the triple bond in A. Draw a stepwise mechanism for this reaction and explain why only ketone B is formed.Ethers are oxidized with O2 to form hydroperoxides that decompose violently when heated. Draw a stepwise mechanism for this reaction.When both carbons ortho to the aryl oxygen are not bonded to hydrogen, an allyl aryl ether rearranges to a parasubstituted phenol. Draw a stepwise mechanism for the following reaction, which contains two [3,3] sigmatropicrearrangements.