6.10 Acid-Catalyzed Hydration of Alkenes. Acid-Catalyzed Hydration of Alkenes

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1 Acid-atalyzed ydration of Alkenes 6.10 Acid-atalyzed ydration of Alkenes + O O reaction is acid catalyzed; typical hydration medium is 50% 2 SO 4-50% 2 O Follows Markovnikov's Rule Follows Markovnikov's Rule % 2 SO 4 50% 2 O O 2 (90%) Follows Markovnikov's Rule Mechanism involves a carbocation intermediate 2 50% 2 SO 4 50% 2 O O (80%) 3 is the reverse of acid-catalyzed dehydration of alcohols to alkenes O + 3 O

2 Addition of Water to Alkene (alcohols) Addition of Water to Alkenes (alcohols) Principle of Microscopic Reversibility Which alkene will undergo acid-catalyzed hydrolysis at the fastest rate? O + A) B) 3 O ) D) In an equilibrium process, the same intermediates and transition states are encountered in the forward direction and the reverse, but in the opposite order. 2 O addition: Markovnikov's Rule The product isolated from the acid-catalyzed hydration of (Z)( Z)-3-methyl-2-pentene is: A) 2-ethyl-2-butanol B) 2-ethyl-1-butanol ) 3-methyl-2-pentanol D) 3-methyl-3-pentanol

3 Addition of Alcohol to Alkenes (ethers) The product isolated from the acid-catalyzed hydration of (E)( E)-3-methyl-2-pentene is: A) chiral B) achiral Stereochemistry of Addition to Alkenes Stereochemistry of Addition to Alkenes + E Y E Y + E Y E Y Regiochemistry withstanding, in order to understand the stereochemistry of the product, you must consider two things: (1) Stereochemistry of the starting alkene (cis or trans; Z or E) (2) Stereochemistry of the addition (syn or anti) Optically inactive reactants produce optically inactive products. (Racemic mixtures are optically inactive) The correlary is that an optically active starting material MAY produce an optically active product depending on the mechanism. The product isolated from the acid-catalyzed hydration of (E)-( or (Z)-3-methyl-2-pentene is: A) optically active B) an optically inactive racemic mixture ) an optically inactive enantiomer 6.12 ydroboration-oxidation of Alkenes

4 Synthesis Suppose you wanted to prepare 1-decanol from 1-decene? Synthesis Two-step reaction sequence called hydroboration- oxidation converts alkenes to alcohols with a regiochemistry opposite to Markovnikov's rule. 1. hydroboration 2. oxidation O Needed: a method for hydration of alkenes with a regioselectivity opposite to Markovnikov's rule. O ydroboration Step ydroboration Step + B 2 B 2 + B 2 B 2 ydroboration can be viewed as the addition of borane (B 3 ) to the double bond. But B 3 is not the reagent actually used. 2 B ydroboration reagents: B 2 Diborane (B 2 6 ) normally used in an ether-like solvent called "diglyme" ydroboration Step Oxidation Step + B 2 B 2 2 O 2, O B 2 O ydroboration reagents: +O B3 Borane-tetrahydrofuran complex ( 3 B-TF) Organoborane formed in the hydroboration step is oxidized with hydrogen peroxide.

5 Example Example 1. B 2 6, diglyme 2. 2 O 2, O B-TF 2. 2 O 2, O O (93%) O (98%) Features of ydroboration-oxidation Example hydration of alkenes regioselectivity opposite to Markovnikov's rule no rearrangement stereospecific syn addition 1. B 2 6, diglyme 2. 2 O 2, O O (82%) Features of ydroboration-oxidation 6.13 Stereochemistry of ydroboration-oxidation hydration of alkenes regioselectivity opposite to Markovnikov's rule no rearrangement stereospecific syn addition

6 syn Addition and O become attached to same face of double bond 1. B O 2, NaO O only product is trans-2-methylcyclopentanol (86%) yield ydroboration-oxidation of which one of the following yields a primary alcohol as the major product? A) B) ) D) B-TF 2. 2 O 2, O O 6.15 Addition of alogens to Alkenes A) The product is achiral B) The product is optically active ) The product is a racemic mixture D) The product is a single enantiomer

7 General features Example + X 2 X X ( ( ) 2 2 l 3 0 ( ( ) 2 electrophilic addition to double bond forms a vicinal dihalide (100%) Scope alogenation limited to l 2 and 2 F 2 addition proceeds with explosive violence I 2 addition is endothermic: vicinal diiodides dissociate to an alkene and I 2 Example 6.16 Stereochemistry of alogen Addition anti addition 2 trans-1,2- -1,2-Dibromocyclopentane 80% yield; only product

8 Example l 2 l l 6.17 Mechanism of alogen Addition to Alkenes: alonium Ions Mechanism is electrophilic addition Addition of alogens to Alkenes 2 is not polar, but it is polarizable two steps (1) formation of bromonium ion (2) nucleophilic attack on bromonium ion by bromide ethylene propene 2-methylpropene trans-1,2- -1,2-Dichlorocyclooctane 73% yield; only product 2,3-dimethyl dimethyl-2-butene Relative Rates of omination 2 = 2 1 = 2 61 ( ) 2 = ( ) 2 =( ) 2 920,000 More highly substituted double bonds react faster. Alkyl groups on the double bond make it more electron rich. Arrange the alkenes in order of decreasing rate of reaction toward bromine addition: 2-methyl-1-butene, 2-methyl-2-butene, and 3- methyl-1-butene A) 2-methyl-1-butene > 3-methyl-1-butene > 2-methyl-2-butene B) 3-methyl-1-butene > 2-methyl-1-butene > 2-methyl-2-butene ) 2-methyl-2-butene > 2-methyl-1-butene > 3-methyl-1-butene D) 2-methyl-2-butene > 3-methyl-1-butene > 2-methyl-1-butene

9 Example 2 trans-1,2- -1,2-dibromocyclopentane 80% yield; 2 asymmetric carbon atoms, hiral product,optically inactive, Racemic mixture, only products formed In general, diastereomers fall into two categories: geometric isomers cis-trans (S) (R) stereoisomers containing two or more asymmetric atoms; (that are not enantiomers) l diastereomers l (R) (R) have different physical properties: BP, MP, density, refractive index, solubility an be separated through conventional means (distillation, recrystallization, chromatography) O 2 O 2 MP = 158 o O 2 O 2 MP = 256 o A compound with n asymmetric carbon atoms can have a maximum of 2 n stereoisomers. (S) (S) Enantiomers 2,3-dibromobutane (R) (R) (R) (S) diastereomers (S) (R) Same compound (meso) Only 3 stereoisomers for 2,3-dibromobutane. σ Three stereoisomers of 2,3-dibromobutane The addition of bromine to cis-2-butene produces: 2R,3R 2S,3S 2R,3S chiral chiral achiral A) A single enantiomer B) A product with one asymmetric carbon atom ) An optically inactive meso product D) A racemic mixture E) 4 different stereoisomers each with 2 chiral carbon atoms

10 The addition of bromine to trans-2-butene produces: A) A single enantiomer B) A product with one asymmetric carbon atom ) An optically inactive meso product D) A racemic mixture E) 4 different stereoisomers each with 2 chiral carbon atoms When naming compounds containing multiple chiral atoms, you must give the configuration around each chiral atom: position number and configuration of each chiral atom, separated by commas, all in ( ) at the start of the compound name (S) l (S) (2S, 3S)-2-bromo-3-chlorobutane Which ones are chiral?? Name each one. Give the stereochemical relationship between them. l l 2 (2S, 3R)-2,3-dichloropentane l l 2 (2R, 3S)-2,3-dichloropentane l l 2 l l l l 2 2 All of them are chiral. l l 2 l l 2 (2S, 3S)-2,3-dichloropentane l l 2 (2R, 3R)-2,3-dichloropentane l l l l l l l l A B D A and B: enantiomers and D: enantiomers A and : diastereomers A and D: diastereomers B and : diastereomers B and D: diastereomers 6.18 onversion of Alkenes to Vicinal alohydrins

11 Addition of alogens in the Presence of Water (halohydrins) + X 2 X X alkenes react with X 2 to form vicinal dihalides + X 2 X X 2 Examples O 2 2 O (70%) alkenes react with X 2 to form vicinal dihalides alkenes react with X 2 in water to give vicinal halohydrins l 2 2 O O + X O X O l + X anti addition: only product 2 Examples O 2 2 O (70%) l 2 2 O O l anti addition: only product

12 Perspective formula Fischer projection Regioselectivity 2 2 O O (77%) 2 Markovnikov's rule applied to halohydrin formation: the halogen adds to the carbon having the greater number of hydrogens... O δ+ 3 3 δ+ 2 : : δ+ Explanation 3 3 : : δ+ δ+ 2 δ+.. O transition state for attack of water on bromonium ion has carbocation character; more stable transition state (left) has positive charge on more highly substituted carbon

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