CHEM 263 Oct 25, stronger base stronger acid weaker acid weaker base
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1 CEM 263 ct 25, 2016 Reactions and Synthesis (Preparation) of R- Breaking the - Bond of R- with Metals R + Li 0 or Na 0 or K 0 metal R Li + 1/2 2 alkoxide Breaking the - Bond of R- by Acid-Base Reaction Examples: Na C 2 C Na + C 3 C 2 strong base sodium ethoxide pk a 16 strong acid weak base pk a 17 weak acid K K strong base pk a 16 strong acid pk a 19 weak acid weak base C 3 Na C 3 Na pka=10 pka=16 stronger base stronger acid weaker acid weaker base Preparation of Alcohols and Ethers from Alkanes Substitution reaction Alkane X 2 h! Elimination reaction Alkyl halide Base Alkene R' R'K R' =, alkyl -R, - Addition reaction R--R' alcohol or ether
2 Example: Br 2 h! Br 2 eat S N 1 Substitution reaction Br K E 1 or E 2 2 Br K (hindered base) Elimination reaction E S Addition reaction 4 + KBr + Preparation of Alcohols and Ethers from Alkenes 2 S 4 Markovnikov Addition C 3 C 3 Mechanism: C 3 3 C C 3 The alkene is first protonated to give a tertiary carbocation, which is then attacked by a lone pair on the oxygen of methanol. This is an intermolecular ether formation, where the reaction occurs between two molecules. 2 2 S S 4 Cineol - seed germination inhibitor Above is and addition of water to limonene, followed by an intramolecular ether formation, where the reaction occurs within the molecule to give cineol. The high local concentration of the reacting groups and the formation of a six-membered ring drive the reaction forward.
3 Mechanism: - + Markovnikov / Anti-Markovnikov Addition: 2 S 4?? = 1. B , Na B 2 6 behaves like B 3, which is a Lewis acid: B The first step of this last example is called hydroboration (syn addition), while the second is an oxidation. This is an example of anti-markovnikov addition. Mechanism: B B B 2 B 2 2 Na 3 B Anti-Markovnikov addition of water with retention of configuration + present in it's salt form in basic condition Borane adds to the least substituted carbon to give the more stable carbocation Syn addition of borane and Na is used for deprotonation of hydrogen peroxide replaces boron with retention of stereochemistry
4 Examples: 1) B 2 6 2) 2 2, Na 1) B 2 6 2) 2 2, Na Note the cis-addition of 2. Preparation of Ethers from Alkenes Epoxidation epoxides can be opened by water 2 ethylene oxide Epoxide formation: 3 C C an epoxide aka oxirane 3 membered ether ring It is a concerted and stereospecific reaction 3 C C formed as racemate (racemic mixture = 1:1 mix of enantiomers) Concerted mechanism: C3
5 Examples: 3 C C formed as racemate (racemic mixture = 1:1 mix of enantiomers) 3 C C formed as single compound (meso compound = achiral but has stereocentres) Note that achiral starting material and (achiral) gives a net achiral product(s). That is, the products are either racemic, or a meso compound. Examples: Is the product of the following reaction one enantiomer or racemic? (racemic reagent equally likely to approach from the top or bottom) C 3 C 3 Disparlure = sex pheromone of Gypsy Moth C 2 human cells C 2 2 Cyclooxygenase Arachidonic Acid = all Z 5,8,11,14-eicosatetraenoic acid Leukotriene A 4 Leukotriene A 4 is an inflammatory signal for asthma and allergic reactions.
6 Alcohols and Ethers from Alkyl alides R-X R R-X RR X = Cl, Br, I, S 2 R Substitution reactions (S N 2, S N 1) S = Substitution N = Nucleophilic 2 or 1 = rate depends on 2 concentrations or 1 concentration S N 2 or - R X R Stereospecific (the stereochemistry of the reactants determines the stereochemistry of the products) Inversion of configuration (Walden Inversion) Concerted (bonds are broken and formed at the same time) Bimolecular 1 halides work the best 2 halides work ok 3 halides don t work In general C=C-X (vinyl halides) also fail for this type of reaction Example: 3 C I + Na C 3 + NaI This is not reversible, because I- is more stable than - Would the following reaction occur? I Na No, this involves a tertiary halide, which is too crowded. Elimination could occur though, to produce:
7 What reagents instead of Na could be used that would allow the above substitution reaction to occur? Answer: 2, 2 S 4 and heat would allow an S N 1 reaction to occur: I 2 2 S 4 heat 2
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