Chapter 11 Alcohols & Ethers. Ch. 11-1
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1 Chapter 11 Alcohols & Ethers Ch. 11-1
2 1. Structure & Nomenclature Alcohols have a hydroxyl ( ) group bonded to a saturated carbon atom (sp 3 hybridized) 1 o 2 o 3 o Ethanol 2-Propanol (isopropyl alcohol) 2-Methyl- 2-propanol (tert-butyl alcohol) Ch. 11-2
3 2-Propenol (allyl alcohol) 2-Propynol (propargyl alcohol) Benzyl alcohol Ch. 11-3
4 Phenols Compounds that have a hydroxyl group attached directly to a benzene ring Cl Phenol 3 C 4-Methylphenol 2-Chlorophenol Ch. 11-4
5 Ethers The oxygen atom of an ether is bonded to two carbon atoms C3 Diethyl ether tert-butyl methyl ether Divinyl ether Ethyl phenyl ether Ch. 11-5
6 1A. Nomenclature of Alcohols Rules of naming alcohols Identify the longest carbon chain that includes the carbon to which the group is attached Use the lowest number for the carbon to which the group is attached Alcohol as parent (suffix) ending with ol Ch. 11-6
7 Examples 2-Propanol (isopropyl alcohol) 1,2,3-Butanetriol Ch. 11-7
8 Example 3-Propyl-2-heptanol 8 or 6 7 wrong Ch. 11-8
9 1B. Nomenclature of Ethers Rules of naming ethers Similar to those with alkyl halides C 3 Methoxy C 3 C 2 Ethoxy Example Ethoxyethane (diethyl ether) Ch. 11-9
10 Cyclic ethers xacyclopropane or oxirane (ethylene oxide) xacyclobutane or oxetane xacyclopentane (tetrahydrofuran or TF) 1,4-Dioxacyclohexane (1,4-dioxane) Ch
11 2. Physical Properties of Alcohols and Ethers Ethers have boiling points that are roughly comparable with those of hydrocarbons of the same molecular weight (MW) Alcohols have much higher boiling points than comparable ethers or hydrocarbons Ch
12 For example Diethyl ether (MW = 74) b.p. = 34.6 o C Pentane (MW = 72) b.p. = 36 o C 1-Butanol (MW = 74) b.p. = o C Alcohol molecules can associate with each other through hydrogen bonding, whereas those of ethers and hydrocarbons cannot Ch
13 Water solubility of ethers and alcohols Both ethers and alcohols are able to form hydrogen bonds with water Ethers have solubilities in water that are similar to those of alcohols of the same molecular weight and that are very different from those of hydrocarbons The solubility of alcohols in water gradually decreases as the hydrocarbon portion of the molecule lengthens; longchain alcohols are more alkane-like and are, therefore, less like water Ch
14 Physical Properties of Ethers Name Formula mp ( o C) Dimethyl ether Diethyl ether Diisopropyl ether 1,2-Dimethoxyethane (DME) xirane C 3 C 3 C 3 C 2 C 2 C 3 (C 3 ) 2 CC(C 3 ) 2 C 3 C 2 C 2 C bp ( o C) (1 atm) Tetrahydrofuran (TF) Ch
15 Physical Properties of Alcohols Name Formula mp ( o C) bp ( o C) (1 atm) * Methanol C inf. Ethanol C 3 C inf. Isopropyl alcohol C 3 C()C inf. tert-butyl alcohol (C 3 ) 3 C inf. exyl alcohol C 3 (C 2 ) 4 C Cyclohexanol Ethylene glycol inf. * Water solubility (g/100 ml 2 ) Ch
16 4. Synthesis of Alcohols from Alkenes Acid-catalyzed ydration of Alkenes C C 2 C C 2 C C C C 2 Ch
17 Acid-Catalyzed ydration of Alkenes Markovnikov regioselectivity Free carbocation intermediate Rearrangement of carbocation possible Ch
18 xymercuration Demercuration C C g(ac) 2 NaB 4 C C C C 2, TF Na gac Markovnikov regioselectivity Anti stereoselectivity Generally takes place without the complication of rearrangements Mechanism Discussed in Section 8.6 Ch
19 ydroboration xidation 1. B 3 TF , Anti-Markovnikov regioselectivity Syn-stereoselectivity Mechanism Discussed in Section 8.7 Ch
20 Markovnikov regioselectivity +, 2 or 1. g(ac) 2, 2, TF 2. NaB 4, Na R R 1. B 3 TF , Na R Anti-Markovnikov regioselectivity Ch
21 Example Synthesis? (1) Synthesis? (2) Ch
22 Synthesis (1) Need anti-markovnikov addition of Use hydroboration-oxidation 1. B 3 TF , Na Ch
23 Synthesis (2) Need Markovnikov addition of Use either acid-catalyzed hydration or oxymercuration-demercuration Acid-catalyzed hydration is NT desired due to rearrangement of carbocation Ch
24 Acid-catalyzed hydration 2 (2 o cation) Rearrangement of carbocation Ch
25 xymercuration-demercuration g(ac) 2 2, TF NaB 4 Na gac Ch
26 5. Reactions of Alcohols The reactions of alcohols have mainly to do with the following The oxygen atom of the group is nucleophilic and weakly basic The hydrogen atom of the group is weakly acidic The group can be converted to a leaving group so as to allow substitution or elimination reactions Ch
27 δ + δ δ + C & bonds of an alcohol are polarized Protonation of the alcohol converts a poor leaving group ( ) into a good one ( 2 ) C + A C + A alcohol strong acid protonated alcohol Ch
28 nce the alcohol is protonated substitution reactions become possible S N 2 Nu + C Nu C + protonated alcohol The protonated group is a good leaving group ( 2 ) Ch
29 6. Alcohols as Acids Alcohols have acidities similar to that of water pk a Values for Some Weak Acids Acid pk a C C 3 C (C 3 ) 3 C 18.0 Ch
30 Relative Acidity 2 > R > RC 2 & alcohols are the strongest acids in this series C > 2 > N 3 > R Increasing acidity Relative Basicity is the weakest acid in this series R > N 2 > > RC C > R > Increasing basicity Ch
31 7. Conversion of Alcohols into Alkyl alides R R X X (X = Cl, Br, I) PBr 3 SCl 2 Ch
32 Examples conc. Cl 25 o C Cl + (94%) PBr 3 Br (63%) Ch
33 8. Alkyl alides from the Reaction of Alcohols with ydrogen alides R + X R X + 2 The order of reactivity of alcohols 3 o > 2 o > 1 o < methyl The order of reactivity of the hydrogen halides I > Br > Cl (F is generally unreactive) Ch
34 R + NaX No Reaction! is a poor leaving group R + NaX R X 3 is a good leaving group R X Ch
35 8A. Mechanisms of the Reactions of Alcohols with X Secondary, tertiary, allylic, and benzylic alcohols appear to react by a mechanism that involves the formation of a carbocation Step fast Ch
36 Step 2 slow + Step 3 + Cl fast Cl Ch
37 Primary alcohols and methanol react to form alkyl halides under acidic conditions by an S N 2 mechanism + X R C X C R + protonated 1 o alcohol or methanol (a good leaving group) Ch
38 9. Alkyl alides from the Reaction of Alcohols with PBr 3 or SCl 2 Reaction of alcohols with PBr 3 3 R + PBr 3 R Br + 3 P 3 (1 o or 2 o ) The reaction does not involve the formation of a carbocation and usually occurs without rearrangement of the carbon skeleton (especially if the temperature is kept below 0 C) Ch
39 Reaction of alcohols with PBr 3 Phosphorus tribromide is often preferred as a reagent for the transformation of an alcohol to the corresponding alkyl bromide Ch
40 Mechanism R Br + P R PBr 2 + Br Br protonated alkyl dibromophosphite Br Br R PBr 2 + R Br + PBr 2 a good leaving group Ch
41 Reaction of alcohols with SCl 2 SCl 2 converts 1 o and 2 o alcohols to alkyl chlorides As with PBr 3, the reaction does not involve the formation of a carbocation and usually occurs without rearrangement of the carbon skeleton (especially if the temperature is kept below 0 C) Pyridine (C 5 5 N) is often included to promote the reaction Ch
42 Mechanism Cl R + Cl S Cl R S Cl N Cl (C 5 5 N) N + R S Cl R S Cl Ch
43 Mechanism N + R S Cl Cl R S N Cl N + S R Cl + S N Ch
44 10. Tosylates, Mesylates, & Triflates: Leaving Group Derivatives of Alcohols Ts = S C 3 (Tosylate) Ms = S C 3 (Mesylate) Ch
45 Direct displacement of the group with a nucleophile via an S N 2 reaction is not possible since is a very poor leaving group + Nu No Reaction! Thus we need to convert the to a better leaving group first Ch
46 Mesylates (Ms) and Tosylates (Ts) are good leaving groups and they can be prepared easily from an alcohol (methane sulfonyl chloride) + C 3 S Cl pyridine same as S C N Cl Ms (a mesylate) Ch
47 Preparation of Tosylates (Ts) from an alcohol (p-toluene sulfonyl chloride) + 3 C S Cl pyridine same as S C N Cl Ts (a tosylate) Ch
48 S N 2 displacement of the mesylate or tosylate with a nucleophile is possible Ts + Nu Nu + Ts Ch
49 Example TsCl Ts Retention of configuration pyridine Inversion of configuration CN NaCN DMS + NaTs Ch
50 Example Retention of configuration Ms MsCl pyridine Inversion of configuration NaSMe DMS SMe Ch
51 11. Synthesis of Ethers 11A. Ethers by Intermolecular Dehydration of Alcohols 2 S o C Ethene 2 S o C Diethyl ether Ch
52 Mechanism + S 3 + S This method is only good for synthesis of symmetrical ethers Ch
53 For unsymmetrical ethers R + R' 1 o alcohols 2 S 4 R R' + R R + Mixture of ethers R' R' Ch
54 Exception R + cat. 2 S 4 R + (good yield) R Ch
55 11B. The Williamson Synthesis of Ethers R' R X R R' (S N 2) Via S N 2 reaction, thus R is limited to 1 o (but R' can be 1 o, 2 o or 3 o ) Ch
56 Example 1 Na Na + 2 Br Ch
57 Example 2 Cl Cl Na 2 Ch
58 Example 3 I Na 2 owever I Na 2 No epoxide observed! Ch
59 11C. Synthesis of Ethers by Alkoxymercuration Demercuration Markovnikov regioselectivity R 1. g( 2 CCF 3 ) 2, R' 2. NaB 4, Na R R' (1) (2) R' R g( 2 CCF 3 ) Ch
60 Example 1. g( 2 CCF 3 ) 2, i Pr 2. NaB 4, Na Ch
61 11D. tert-butyl Ethers by Alkylation of Alcohols: Protecting Groups 2 S 4 R + R A tert-butyl ether can be used to protect the hydroxyl group of a 1 o alcohol while another reaction is carried out on some other part of the molecule tert-butyl protecting group A tert-butyl protecting group can be removed easily by treating the ether with dilute aqueous acid Ch
62 Example Synthesis of from Br and BrMg 5 4 Ch
63 Direct reaction will not work BrMg + Br (Not Formed) Since Grignard reagents are basic and alcohols contain acidic proton BrMg + BrMg Br Br + Ch
64 Need to protect the group first tert-butyl protected alcohol Br 1. 2 S 4 2. Br BrMg 2 deprotonation Ch
65 11E. Silyl Ether Protecting Groups A hydroxyl group can also be protected by converting it to a silyl ether group R + Me Cl Si Me t Bu tert-butylchloro dimethylsilane (TBSCl) imidazole DMF ( Cl) R Me Si Me t Bu ( R TBS) Ch
66 The TBS group can be removed by treatment with fluoride ion (tetrabutylammonium fluoride or aqueous F is frequently used) R Me Si Me t Bu Bu 4 N + F TF R + Me F Si Me t Bu ( R TBS) Ch
67 Example Synthesis of Ph from I and Ph 6 5 Na Ch
68 Direct reaction will not work Ph Na (Not Formed) + Ph I Instead Na + Ph + Ph I I Ch
69 Need to protect the group first I TBSCl imidazole DMF TBS Na I Ph TBS Ph Bu 4 N F TF Ph Ch
70 12. Reactions of Ethers Dialkyl ethers react with very few reagents other than acids + Br + Br an oxonium salt Ch
71 12A. Cleavage of Ethers eating dialkyl ethers with very strong acids (I, Br, and 2 S 4 ) causes them to undergo reactions in which the carbon oxygen bond breaks + 2 Br 2 Br + 2 Cleavage of an ether Ch
72 Mechanism + Br + Br Br + Br + Br + Br Ch
73 13. Epoxides Epoxide (oxirane) A 3-membered ring containing an oxygen Ch
74 13A. Synthesis of Epoxides: Epoxidation Electrophilic epoxidation peroxy C C C C acid Ch
75 Peroxy acids (peracids) R C Common peracids Cl C 3 C C meta-chloroperbenzoid acid (MCPBA) peracetic acid Ch
76 Mechanism peroxy acid R R carboxylic acid R alkene concerted transition state epoxide Ch
77 13B. Stereochemistry of Epoxidation Addition of peroxy acid across a C=C bond A stereospecific syn (cis) addition MCPBA (trans) (trans) MCPBA (cis) (cis) Ch
78 Electron-rich double reacts faster MCPBA (1 eq.) Ch
79 14. Reactions of Epoxides The highly strained three-membered ring of epoxides makes them much more reactive toward nucleophilic substitution than other ethers Ch
80 Acid-catalyzed ring opening of epoxide C C + C C + + C C C C Ch
81 Base-catalyzed ring opening of epoxide R R + C C C C R R C C + R Ch
82 If the epoxide is unsymmetrical, in the base-catalyzed ring opening, attack by the alkoxide ion occurs primarily at Et the less substituted carbon atom + Et 1 o carbon atom is less hindered Et Et + Et Ch
83 In the acid-catalyzed ring opening of an unsymmetrical epoxide the nucleophile attacks primarily at the more substituted carbon atom Me + cat. A Me Me + (protonated epoxide) Me This carbon resembles a 3 o carbocation Ch
84 15. Anti 1,2-Dihydroxylation of Alkenes via Epoxides Synthesis of 1,2-diols cold KMn 4, or 1. s 4 2. NaS 3 1. MCPBA 2. +, 2 Ch
85 Anti-Dihydroxylation A 2-step procedure via ring-opening of epoxides MCPBA Ch
86 16. Crown Ethers Crown ethers are heterocycles containing many oxygens They are able to transport ionic compounds in organic solvents phase transfer agent Ch
87 Crown ether names: x-crown-y x = ring size y = number of oxygen (18-crown-6) (15-crown-5) (12-crown-4) Ch
88 Different crown ethers accommodate different guests in this guest-host relationship 18-crown-6 for K + 15-crown-5 for Na + 12-crown-4 for Li Nobel Prize to Charles Pedersen (Dupont), D.J. Cram (UCLA) and J.M. Lehn (Strasbourg) for their research on ion transport, crown ethers Ch
89 Many important implications to biochemistry and ion transport KMn 4 benzene K Mn 4 (18-crown-6) (purple benzene) Ch
90 Several antibiotics call ionophores are large ring polyethers and polylactones Me Me Me Me Me Me Me Me Nonactin Ch
91 17. Summary of Reactions of Alkenes, Alcohols, and Ethers Synthesis of alcohols X (1 o alcohol) 1. B 3 TF , Na MgBr Ch
92 Synthesis of alcohols 1. B 3 TF , Na +, 2 (2 o alcohol) 1. g(ac) 2, 2 2. NaB 4 or Ch
93 Synthesis of alcohols X 2 +, 2 (3 o alcohol) 1. g(ac) 2, 2 2. NaB 4 Ch
94 Reaction of alcohols Br R PBr 3 SCl 2 Cl 1. base 2. R-X (1 o alcohol) -X X +, heat TsCl pyridine TS Ch
95 Synthesis of ethers R R R conc. 2 S o C R X R Cleavage reaction of ethers R R' X X R R' R +R'X Ch
96 END F CAPTER 11 Ch
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