Physical Properties. Alcohols can be: CH CH 2 OH CH 2 CH 3 C OH CH 3. Secondary alcohol. Primary alcohol. Tertiary alcohol

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1 Chapter 10: Structure and Synthesis of Alcohols 100

2 Physical Properties Alcohols can be: CH 3 CH 3 CH CH 2 OH * Primary alcohol CH 3 OH CH * CH 2 CH 3 Secondary alcohol CH 3 CH 3 * C OH CH 3 Tertiary alcohol 101

3 Most alcohols (C 1 -C 12 ) are liquids at room temperature Bp much higher than alkanes of similar molecular weights (H-bonding) 102

4 Acidity: the H of the hydroxyl group is weakly acidic: 103

5 This hydroxyl proton can be removed with suitable bases. Bases such as KOH or NaOH are not strong enough. NaH, KH or Na (s), K (s) are usually used. 104

6 In the case of phenols, the pka of the hydroxyl group is around 10 and weaker bases can be used (NaOH, KOH, etc ) 105

7 Synthesis of Alcohols Hydration (a) Direct (8.4) (Review) 106

8 Mechanism of Direct Hydration of Alkenes 107

9 (b) Indirect (4.8) (1) Oxymercuration/Demercuration (8.5) (2) Hydroboration/Oxidation (8.7) 108

10 Hydroxylation (8.14) 109

11 New Synthesis of Alcohols (Nu attack on carbonyl compounds) An excellent method to make alcohols. Depending on the type of carbonyl used, primary, secondary and tertiary alcohols are all available from this reaction. 110

12 2 types of reagents can deliver nucleophilic carbons to C=O: Grignard reagent: R-Mg-X Alkyl Lithium: R-Li δ δ+ δ δ+ R M gx R Li 111

13 Synthesis of Grignard Reagents (10.8) Br + Mg ether MgBr Cl CH 3 CHCH 2 CH 3 MgCl ether + Mg CH 3 CHCH 2 CH 3 112

14 Alkyl Lithium can be prepared in a similar way: 113

15 Synthesis of 1 o Alcohols (10.9) Grignards or alkyl lithium react with formaldehyde to produce primary alcohols. The carbon chain increases by one carbon from the original organometallic reagent. 114

16 Synthesis of 2 o Alcohols (10.9) other aldehydes react to give secondary alcohols with either Grignard reagents or alkyl lithiums to produce secondary alcohols 115

17 Synthesis of 3 o Alcohols (10.9) reaction of ketones with RLi or RMgX will produce tertiary alcohols 116

18 3 o Alcohols by Acyl Substitution (10.9) acid chlorides and esters react with either Grignard reagents or alkyl lithiums via the acyl substitution mechanism. Since the resulting product is a ketone, the reaction will continue and eventually produce the corresponding tertiary alcohol. 117

19 Mechanism of Acyl Substitution In the presence of a Grignard or alkyl lithium the reaction will first produce a ketone which will continue to react to produce the corresponding 3 o alcohol. 118

20 Here is an example of this reaction using two equivalent of grignard reagent with an ester. 119

21 1 o Alcohols With 2 Extra Carbons on the Alkyl Chain. (10.9) These compounds are generated by the reaction of RLi or RMgX with epoxides. Epoxides are electrophilic due to the ring strain. 2 extra carbons will be added to the alkyl chain. 120

22 Limitations of Grignard Reagents Grignards are good nucleophiles but in the presence of acidic protons it will acts as a strong base. No water or other acidic protons like O H, N H, S H, or terminal alkynes. No other electrophilic multiple bonds, like C N, C N, S O, or N O. 121

23 Practice Question What is the major organic product of the following reactions. Disregard stereoisomers. 122

24 3-Methyl-3-hexanol can be prepared from the reaction of 2-pentanone and ethylmagnesium bromide as shown below. What other combination or grignards and ketones can be used to prepare this compound? O 1) CH3CH2M gbr 2) H3O+ OH 123

25 Reduction of Carbonyl Compounds (10.11) Reduction of the carbonyl group also produces alcohol by nucleophilic attack to the carbon of the carbonyl. In this case the nucleophile is the hydride ion. Protonation of the resulting alkoxide ion gives the alcohol. 124

26 2 common reagents to carry out this transformation are : LiAlH 4 : lithium aluminum hydride NaBH 4 : sodium borohydride 125

27 NaBH 4 is selective only for ketones, aldehydes and acid chlorides. LiAlH 4 will reduce all carbonyl compounds. 126

28 This selectivity can be used in synthesis to control which functional group reacts. 127

29 Mechanism of Hydride Reduction of Carbonyls (Ketones and Aldehydes) 128

30 Mechanism of Acid Chloride/Ester Reduction In the case of esters and acid chlorides, two equivalents of the hydride are transferred since the first product is a ketone. 1 o alcohols are produced. 129

31 Catalytic Hydrogenation (10.11) Similar to the hydrogenation of alkene seen in CHEM201, addition of H 2 to the carbonyl of ketones and aldehydes is possible resulting in the formation of alcohols. 130

32 This reaction is also complementary to the reduction using metal hydrides as it allow for other reduction to take place. 131

33 Practice Questions Complete the following reactions. NaBH 4 COOCH 3 MeOH 132

b.p.=100 C b.p.=65 C b.p.=-25 C µ=1.69 D µ=2.0 D µ=1.3 D

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