Chapter 12. Alcohols from Carbonyl Compounds Oxidation-Reduction & Organometallic Compounds. Structure

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1 Chapter 12 Alcohols from Carbonyl Compounds xidation-eduction & rganometallic Compounds Created by Professor William Tam & Dr. Phillis Chang Structure ~ 120 o ~ 120 o C ~ 120 o Carbonyl carbon: sp 2 hybridized Planar structure Polarization and resonance structure C C 1A. eactions of Carbonyl Compounds with Nucleophiles ne of the most important reactions of carbonyl compounds is nucleophilic addition to the carbonyl group Nu C nucleophilic addition Nu C 1

2 Nucleophilic Addition eactions of Aldehydes and Ketones Aldehydes more reactive toward nucleophilic addition than ketones Aldehydes less sterically hindered than ketones Two important nucleophiles: ydride ions (from NaB 4 and LiAl 4 ) Carbanions (from Li and MgX) Another important reaction: oxidation C reduction 1 o alcohol aldehyde 2. xidation-eduction eactions in rganic Chemistry eduction of an organic molecule usually corresponds to increasing its hydrogen content or decreasing its oxygen content The opposite reaction of reduction is oxidation. Increasing the oxygen content of an organic molecule or decreasing its hydrogen content is oxidation carboxylic acid oxygen content decreases [] reduction aldehyde hydrogen content increases [] reduction [] C 3 [] lowest oxidation state [] [] [] [] highest oxidation state 2

3 xidation of an organic compound may be more broadly defined as a reaction that increases its content of any element more electronegative than carbon [] [] [] Ar C 3 Ar C 2 Cl Ar CCl 2 Ar CCl 3 [] [] [] 2A. xidation States in rganic Chemistry ules For each C (or C M) bond -1 For each C C bond 0 For each C Z bond +1 (where M = electropositive element and is equivalent to, e.g. Li, K, etc.; Z = electronegative heteroatom, e.g., S, P 2, halogen, etc.) Examples Calculate the oxidation state of each carbon based on the number of bonds it is forming to atoms more (or less) electronegative than carbon (1) C Bonds to C: 4 to = (- 1) x 4 = - 4 Total = - 4 xidation state of C = - 4 3

4 Examples Examples (2) C Bonds to C: 3 to = to = +1 Total = - 2 (3) C Bonds to C: 2 to = to = +2 Total = 0 xidation state of C = - 2 xidation state of C = 0 Examples verall order (4) Bonds to C: C 1 to = to = +3 Total = +2 xidation state of C = +2 C oxidation state lowest oxidation state of carbon < C < C < C < C highest oxidation state of carbon 4

5 Quiz 1 3. Alcohols by eduction of Carbonyl Compounds [] Quiz 2 ' [] [] (1 o alcohol) [] 2014 by John Wiley & Sons, Inc. All rights reserved. ' ' 5

6 3A. Lithium Aluminum ydride LiAl 4 (LA) Not only nucleophilic, but also very basic eacts violently with 2 or acidic protons (e.g. ) Usually reactions run in ethereal solvents (e.g. Et 2, TF) educes all carbonyl groups Examples 3B. Sodium Borohydride (1) (2) (3) ' 1. LiAl 4, Et , 2 1. LiAl 4, Et , 2 1. LiAl 4, Et , 2 + ' NaB 4 less reactive and less basic than LiAl 4 can use protic solvent (e.g. ) reduces only more reactive carbonyl groups (i.e. aldehydes and ketones) but not reactive towards esters or carboxylic acids 6

7 Examples (1) NaB 4 2 (2) ' NaB 4 2 ' chanism ' + B ' 3C. verall Summary of LiAl 4 and NaB 4 eactivity reduced by LiAl 4 reduced by NaB 4 ' < ' < ' < Aldehydes are reduced to 1 alcohols & ketones are reduced to 2 alcohols ease of reduction 7

8 3D. eduction of Alkyl alides to ydrocarbons: X 4. xidation of Alcohols 8

9 4A. A Common chanistic Theme Alcohol oxidation by elimination Aldehyde Aldehyde hydrate Carboxylic acid A 1 or 2 alcohol reacts with a reagent that installs a leaving group (LG) on the alcohol oxygen atom In an elimination step, a base removes a hydrogen from the alcohol carbon, the bond forms, and the leaving group departs, resulting in the oxidized product 4B. Swern xidation Swern oxidation of a 1 alcohol to an aldehyde 1. DMS, (CCl) 2,-60 o C 2. Et 3 N Swern oxidation of a 2 alcohol to a ketone 9

10 4C. Chromic Acid ( 2 Cr 4 ) xidation Chromic acid ( 2 Cr 4 ) usually prepared by [Cr 3 or Na 2 Cr 2 7 ] + aqueous 2 S 4 Jones reagent Jones oxidation eagent: Cr 3 + aqueous 2 S 4 A Cr(VI) oxidant ' " ' Cr 3 2 S 4 (orange solution) Cr 3 2 S 4 (orange solution) Cr 3 2 S 4 ' No eaction + Cr(III) (green) + Cr(III) (green) 10

11 chanism of chromate acid oxidations Formation of the chromate ester 3 C C + Cr 3 C 3 C 3 C 3 C Cr 3 C + C 3 C 3 C Cr C Cr C The oxidation step 3 C 3 C Cr C + Cr 3 C C 3 C + + A Chemical Test for Primary and Secondary Alcohols ' " ' Cr 3 2 S 4 (orange solution) Cr 3 2 S 4 (orange solution) Cr 3 2 S 4 ' No eaction + Cr(III) (green) + Cr(III) (green) 11

12 4D. Pyridinium Chlorochromate (PCC) PCC oxidation eagent PCC = N [Cr 3 Cl] (Pyridinium chlorochromate) Cr 3 + Cl + N N [Cr 3 Cl] Pyridine (C 5 5 N) Pyridinium chlorochromate (PCC) PCC oxidation PCC C 2 Cl 2 PCC ' C 2 Cl 2 ' ' PCC C 2 Cl 2 No eaction 12

13 4E. Potassium Permanganate (KMn 4 ) 5. rganometallic Compounds KMn 4, 2, heat 3 K Compounds that contain carbon-metal bonds are called organometallic compounds C M C : M C M primarily ionic (M = Na or K) (M = Mg or Li) primarily covalent (M = Pb, Sn, g or Tl) 13

14 rganometallic Compounds 6. Preparation of rganolithium & rganomagnesium Compounds 6A. rganolithium Compounds Preparation of organolithium compounds Et 2 X + 2 Li (or TF) Li + LiX rder of reactivity of X I > Br > Cl Example Br + 2 Li Et 2-10 o C (80% - 90%) Li + LiBr 14

15 6B. Grignard eagents Preparation of organomagnesium compounds (Grignard reagents) X + Mg Et 2 MgX Ar X + Mg Et 2 ArMgX rder of reactivity of X I > Br > Cl Example Br + Mg TF MgBr 7. eactions of rganolithium and rganomagnesium Compounds 7A. eactions with Compounds Containing Acidic ydrogen Atoms MgX ~ :MgX Li ~ :Li 15

16 Grignard reagents and organolithium compounds are very strong bases Examples As base MgX + Y + Y + Mg 2+ + X (or Li) (Y =, N or S) (2) MgBr + C 3 + C 3 + Mg 2+ +Br Examples As base (3) + 3 C MgBr 7B. eactions of Grignard eagents with Epoxides (xiranes) Grignard reagents react as nucleophiles with epoxides (oxiranes), providing convenient synthesis of alcohols MgBr + C 3 A good method for the preparation of alkynylmagnesium halides 16

17 Via S N 2 reaction Also works for substituted epoxides, 2 (1 o alcohol) 7C. eactions of Grignard eagents with Carbonyl Compounds chanism ' + "MgX 1. Et " ' ' + " MgX MgX ' " ' = (aldehyde) ' = alkyl (ketone) ' " 17

18 8. Alcohols from Grignard eagents, = (formaldehyde) 1 o alcohol ' + "MgX ' = (aldehyde) ' = alkyl (ketone) 1. Et " ' MgX + formaldehyde MgX o alcohol = alkyl, = (higher aldehydes) 2 o alcohol, = alkyl (ketone) 3 o alcohol MgX + ' higher aldehyde MgX ' 3 + MgX + ' " ketone MgX " ' N 3 Cl 2 ' 2 o alcohol ' " 3 o alcohol 18

19 eaction with esters 3 o alcohol ' + "MgX (2 equiv.) 1. Et " " + ' chanism + " MgX ' " " MgX " " MgX ' " ' + " " MgX Examples Examples (1) MgBr + Et 2 (2) MgI + 3 C Et 2 MgBr MgI 3 + C C 3 (1 o alcohol) (2 o alcohol) 19

20 Examples (3) MgBr + Ph Ph Et 2 Examples (4) MgI + Ph Et 2 Ph MgI MgI MgI Ph Ph 3 + Ph Ph Ph Ph (3 o alcohol) MgBr 3 + Ph (3 o alcohol) 8A. ow to Plan a Grignard Synthesis Synthesis of thod 1 etrosynthetic analysis Synthesis MgBr + 1. Et

21 thod 2 etrosynthetic analysis thod 3 etrosynthetic analysis disconnection Et + 2 MgBr Synthesis disconnection Synthesis MgBr + 1. Et Et 1. Et MgBr B. estrictions on the Use of Grignard eagents Grignard reagents are useful nucleophiles but they are also very strong bases It is not possible to prepare a Grignard reagent from a compound that contains any hydrogen more acidic than the hydrogen atoms of an alkane or alkene A Grignard reagent cannot be prepared from a compound containing an group, an N group, an S group, a C 2 group, or an S 3 group Since Grignard reagents are powerful nucleophiles, we cannot prepare a Grignard reagent from any organic halide that contains a carbonyl, epoxy, nitro, or cyano ( CN) group 21

22 Grignard reagents cannot be prepared in the presence of the following groups because they will react with them:, N 2, N, C 2, S 3, S, C C,,, N 2, C N,, N 2, 8C. The Use of Lithium eagents Li + organolithium reagent aldehyde or ketone Li lithium alkoxide rganolithium reagents have the advantage of being somewhat more reactive than Grignard reagents although they are more difficult to prepare and handle 3 + alcohol 8D. The Use of Sodium Alkynides Preparation of sodium alkynides 9. Protecting Groups eaction via ketones (or aldehydes) Br I ow? 22

23 etrosynthetic analysis Need to protect the group first MgBr + Br (protection) "P" Br owever disconnection Br Mg Et 2 Br MgBr "P" (deprotection) Mg, Et 2 MgBr "P" (no acidic group) BrMg acidic proton powerful base Synthesis Br TBSCl = t Bu Si Cl TBSCl imidazole DMF (protection) TBS Mg, Et 2 Br Quiz 1 Imidazole = N N DMF = N (a polar aprotic solvent) Bu 4 N F TF (deprotection) TBS TBS MgBr 23

24 Quiz 2 Quiz 3 Quiz 4 24

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