Chapter 10 Problems , 42-43,
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1 Chapter 10 Problems , 42-43, Synthetic Uses of Substitution and Elimination Reactions This chapter discusses how one can use substitution and elimination reactions to synthesize organic molecules Substitution Reactions Reactions that proceed via the S N 2 mechanism are preferred. Changes in stereochemistry and rearrangements are observed for S N 1 reactions. Substrates with leaving groups attached to 1 o and methyl carbons are excellent S N 2 reactants, 2 o carbons are ok as long as the nucleophile is weakly basic. S N 1 reactions must be used for substrates with leaving groups attached to 3 o carbons Preparation of Alcohols Alcohols can be prepared for alkyl halides using either HO - or H 2 O as a nucleophile. Hydroxide ion reacts with 1 o alkyl halides or 2 o halides that are either benzylic, allylic, or adjacent to a carbonyl. Examples Hydroxide is not typically used for 3 o alkyl halides due to the competing E2 reaction. Water is used as the nucleophile and reactions follow an S N 1 mechanism. Example The reaction of 2 o alkyl halides with hydroxide gives poor yield of substitution products to the competing E2 reaction. So one can use a less basic hydroxide alternative acetate (CH 3 CO 2 - ). Acetate gives better yield of substitution product and then subsequent reaction with hydroxide yields the desired alcohol. Example
2 10.3 Preparation of Ethers Ethers can be formed by using alcohols or alkoxide as the nucleophile. When alkoxide is used as the nucleophile the reaction is termed the Williamson Ether Synthesis. Example Unsymmetrical ethers can be prepared via two different Williamson ether syntheses. Since alkoxides are strong bases one would prefer to use 1 o or Methyl alkyl halides when possible. Ethers can also be prepared by using alcohols as the nucleophile when the leaving group is attached to a secondary or tertiary carbon. Cyclic ethers are readily formed if the resulting ring is 3, 5, or 6 membered.
3 10.4 Preparation of Esters Esters can be prepared by using carboxylate salts as nucleophiles. Elimination is not a problem due to the low basicity of carboxylates. Ex Preparation of Alkyl Halides Alkyl halides are frequently prepared from alcohols. Since HO - is a poor leaving group the OH group must be converted into a better leaving group, -OH 2 +, -OTs, or OMs, Or via reaction with SOCl 2, PBr 3, or PCl 3. Or displacement by another halide Preparation of Amines Ammonia and unhindered amines are good nucleohpiles. Reaction of 2 o or 3 o amines with alkyl halides provides a good yield of 3 o amines or quaternary ammonium salts. 1 o amines and ammonia have significant problems with multiple alkylations.
4 The Gabriel synthesis of 1 o amines was developed to overcome this problem. The Gabriel synthesis uses Phthalimide as an ammonium equivalent Preparation of Hydrocarbons Hydrocarbons can prepared by replacing a leaving group with a hydrogen. Lithium aluminum hydride (LiAlH 4 ) and sodium borohydride (NaBH 4 ) react as nucleophilic hydride ion. These compounds are also basic and have problems when the leaving group is on a 3 o carbon Formation of Carbon-Carbon Bonds The formation of C-C bonds is one of the more difficult tasks in organic chemistry. This usually requires the use of a carbon nucleophile carbanion. The first case is the cyanide ion ( - CN) which is a weak base but good nucleophile. Yields are good for Me, 1 o and 2 o substrates. Example A second important type of carbon nucleophile are acetylide anions R-C C: -. These anions are generated by reaction of terminal alkynes with a strong base. EX: Acetylide anions are both good nucelophiles and strong bases. Thus S N 2 reactions are favorable with Me and 1 o substrates but 2 o and 3 o give mainly elimination products. EX:
5 10.9 Phosphorus and Sulfur Nucleophiles Sulfur compounds are weaker bases but stronger nucleophiles than the corresponding oxygen compounds. Elimination reactions are not usually a problem for Me, 1 o, or 2 o substrates. EX Phosphorus nucleophiles, most frequently triphenylphosphine, are also useful Ring Opening of Epoxides While most ethers are unlikely to undergo substitution reactions, the ring strain in epoxides allows one of the C-O bonds to be broken in a substitution reaction. These reactions can be done either under acidic or basic conditions. Under basic conditions the reaction follows and S N 2 mechanism which inverts the stereocenter and the substitution occurs at the less hindered site. Ex When the reaction is conducted under acidic conditions the reaction follows a mechanism between S N 1 and the S N 2. The substitution occurs at the more stable more substituted carbon, but still occurs with retention. Ex Elimination of Hydrogen Halide (Dehydrohalogenation) Elimination reactions provide good yields of alkenes, as long as the reactions are conducted under conditions which limit the competing substitution products. However, one also encounters problems with the regio-control of the reactions (Zaitsev, Hofmann, cis/trans) Ex Preparation of Alkynes Alkynes can be prepared from dihaloalkanes by elimination of twp equivalents of HX. This reaction usually requires a strong base (KOH at high T or NaNH 2 ). Ex
6 10.13 Dehydration While one can use HX to convert alcohols to alkyl halides, the use of sulfruric or phosphoric acid results in elimination (termed dehydration). Ex Eliminations to form Carbon-Oxygen Bonds; Oxidation Reactions In organic chemistry oxidation is a reaction that results in an increase in the oxygen content or decrease in the hydrogen content of a compound, reduction is a reaction that decreases the oxygen content or increases the hydrogen content. Ex.
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