The carbonyl C = O H C = O C = O O R C - O. acetone. aldehyde. ketone H + Carboxylic acids. d - d + Phosgene! COCl 2 Chemical weapon
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1 d + d - C = O The carbonyl acetone H C = O aldehyde R R C = O ketone R O R C - O Paolo Sarti 2011 Department of Biochemistry Sapienza H + Carboxylic acids Phosgene! COCl 2 Chemical weapon
2 Paolo Sarti 2011 Department of Biochemistry Sapienza Aldehydes structure
3 Paolo Sarti 2011 Department of Biochemistry Sapienza Familiar names & IUPAC
4 Paolo Sarti 2011 Department of Biochemistry Sapienza Aldehydes & Ketons
5 Paolo Sarti 2011 Department of Biochemistry Sapienza The carbonyl
6 d - d + C = O Carbonyl properties: both C & O are sp2 hybrids polarized bond 165 Kcal/mol stabilized average bond length 1.22 Å Depending on R ed R : different inductive effects Reactivity of aldheydes and ketons Paolo Sarti 2011 Department of Biochemistry Sapienza
7 Ketones Nomenclature alk ane one Again, try to figure out the 3D organization of the molecule! Paolo Sarti 2011 Department of Biochemistry Sapienza
8 Ketones R ed R = alkyl- or aryl-derivatives/substituents Nomenclature: IUPAC & familiar/common Paolo Sarti 2011 Department of Biochemistry Sapienza
9 Aldehydes common reactions oxidation alcohol aldehyde acid reduction Paolo Sarti 2011 Department of Biochemistry Sapienza
10 Carbonyl reactivity (aldehydes & ketones) d - d + C = O d + C = O d H + cat C O H + cat Carbocation (stabilized by H + ) Addition to double bond d - d + C = O + H + + Nu Nu + C - O Nu C OH Trigonal sp2 Intermediate sp3 Final, sp3 (Ex. Nu = H-OH, R-OH, R-SH, HCN, NH 3 ) Paolo Sarti 2011 Department of Biochemistry Sapienza H + cat
11 Double bond, nucleophylic addition d - d + C = O d + d H + cat C = O C O H C OH Nu Final, sp3 Carbo-cation (stabilized by resonance) Paolo Sarti 2011 Department of Biochemistry Sapienza
12 H 2 O addition R R d - d + C = O sp2 + H-OH R R C OH OH Hydrated keton R d - d + C = O + H-OH R H C OH H sp2 OH Hydrated aldehyde Paolo Sarti 2011 Department of Biochemistry Sapienza
13 R-OH, R-SH addition R d - d + C = O + R -OH R H sp3 C O R H sp2 OH Aldehyde + Alcohol Hemi-acetal Glucose cyclization R R d - d + C = O sp2 ketone + + R -OH Alcohol R R sp3 OH C O R Hemi-ketal Paolo Sarti 2011 Department of Biochemistry Sapienza Fructose cyclization
14 Paolo Sarti 2011 Department of Biochemistry Sapienza MUTAROTATION (H 2 O, 20 C) (112-52) = 0.64 = 64% b (112-19) a, pure (crystallized in methanol) [a] = 112 b, pure (crystallized in acetic ac. ) [a] = % a (+) (+) % b b increases a increases
15 Glucose ; specific optical rotation a, pure (in methanol) [a] = 112 b, pure (in acetic ac. ) [a] = 19 Specific optical rotation [a] = +52 time = t eq anomeric carbon anomeric carbon a-d-glucose a-d-glucose a-d-glucose Paolo Sarti 2011 Department of Biochemistry Sapienza
16 Glucides dimerization - polymerization hemiacetal + hemiacetal acetal + H 2 O O bond (ether)
17 keto-enol tautomerization Definition : two isomers are reciprocal tautomers if (within the molecule) there might occur the transfer of: 1) 1 p electron-pair 2) 1 H a - this typically occurs between : 1 carbonyl C & 1 a C (keto-enol) 1 carbonyl C & 1 a N (nucleic a. bases G, T, U) 1 imine N & 1 a N (nucleic a. bases A, C) Involving C = O Carbonyl C C = N-H imine N
18 Keto-enol Tautomerism Properties of an ac ac displays acidic properties!! Ca H 1 carbonilic C & 1 a C C = O C a = C Keto-enol Tautomers OH O CH 3 - C - CH 3 Acetone (di-methylketone, propanone) OH CH 2 = C CH 3 keto enol
19 -NHa, displays acidic properties! a position (C,N) definition & properties 1 carbonilic C & 1 an Na H keto C = O N a = C enol OH 1 imine and 1 an Na H C = N - H N a = C H N H imine keto, lactam form amine enol, lactim form
20 C = O & an
21 A curiosity lactams curiosity saccharin b g d e greek letter = n of C in the ring out of carbonyl
22 b-lactames inhibit bacterial cell wall synthesis b b-lactam ring penicillins cephalosporins
23 DNA bases: keto-enol tautomerism 1 iminic N and 1 N a 1 carbonilic C and 1 N a
24 DNA bases : keto-enol tautomerism & H-bonds a = H bond acceptor d = H bond donor a d a a d 1 N iminic and 1 N a d a d d a 1 C carbonylic and 1 N a saccharin
25 5 3 direction 5 3 direction 5 end Hydrogen 3 end bonds adenine thymine thymine adenine cytosine guanine 3 end guanine cytosine 5 end
26 Il DNA nativo double è una helix doppia (DNA) elica di catene antiparallele OVERALL complementari PICTURE
27 CARBOXYLIC ACIDS
28 CARBOXYLIC ACIDS mono- di- poly- O R C - O Carboxyl group H + O R C - O Carboxylate ion + H + p bond resonance
29 Some organic acids
30 Others : watch R! (inductive effects) Ka = 1.77 x 10-4 pka= 3.75 Ka = 1.34 x 10-5 pka= 4.87 Ka = 1.8 x 10-5 pka= 4.75 pka= 3.5 Ka = 1.07 x 10-3 pka= 1.96 Ka = 7,24 x 10-3 pka= 2.14 aspirin (acetyl-salicylic acid) Ka = 1.4 x 10-5 pka= 4.84
31
32 Methanoic vs butanoic acid pka = 3.74 Ka = = 1.8 x 10-4 pka = 4.82 Ka = = 1.5 x 10-5
33 Most common reactions Oxidation alcohol aldehyde acid Reduction
34 mono-carboxylic acids HCOOH formic acid methanoic acid CH 3 COOH acetic ethanoic CH 3 CH 2 COOH propionic propanoic CH 3 CH 2 CH 2 COOH butyric butanoic CH 3 (CH 2 ) 4 COOH hexanoic capronic CH 3 (CH 2 ) 6 COOH octanoic caprylic CH 3 (CH 2 ) 8 COOH decanoic caprynic C 6 H 5 COOH benzoic
35 Inductive effects & acidity (mono-carboxylic) Carboxylic Acid Structure pka Ethanoic acid CH 3 -COOH 4.7 Propanoic acid CH 3 CH 2 -COOH 4.9 Fluoroethanoic acid CH 2 F-COOH 2.6 Chloroethanoic acid CH 2 Cl-COOH 2.9 Dichloroethanoic acid CHCl 2 -COOH 1.3 Trichloroethanoic acid CCl 3 -COOH 0.9 Nitroethanoic acid O 2 NCH 2 -COOH 1.7
36 acidity high acidity low
37 di-carboxylic acids (K a1 vs K a2!) K a1 K a2 HOOC COOH oxalic ac 5.4 x x 10-5 HOOC-CH 2 -COOH malonic 1.4 x x 10-5 HOOC-(CH 2 ) 2 -COOH succinic 6.2 x x 10-5 HOOC-(CH 2 ) 3 -COOH glutaric 4.6 x x 10-5
38 Fischer Esterification R HO C = O sp2 + R -OH Nu R HO + C OH R R O C = O sp2 + H 2 O sp3 acid + alcohol intermediate ester + H 2 O O O R C + R R C OH HO O R + H 2 O H + ester
39 The mechanism (Fischer) Catalytic H + unstable sp3 Intermediates R R + R + R + H + sp2 (initial) nucleophilic attack Ester bond R R R hydrated Pole formation R + H + final sp2
40 Fischer mechanism : relevant steps
41 dicarboxylic (inductive effects) Oxalic ac. Malonic ac. Succinic ac. HOOC COOH pk a pk a HOOC CH 2 COOH pk a pk a HOOC (CH 2 ) 2 COOH pk a pk a2 5.64
42 di-benzoic acids Acido ftalico pk a pk a orto meta para
43 Fatty acid salts & detergents
44
45 LDL VLDL (TG) HDL
46 lode Ma anche salutari!? OH - H NH SH Kw=[H + ] [OH - ] 23 Ka=a 2 C ph=-log [H + ] 20 Ki=Kw/Ka 18 -CHO -COOH Paolo Sarti 2011 Department of Biochemistry Sapienza Buon Natale a Voi tutti!
47 Aldehydes Nomenclature alk ane * anal (but see also common/familiar names) Paolo Sarti 2011 Department of Biochemistry Sapienza
48 Paolo Sarti 2011 Department of Biochemistry Sapienza Aldehydes Nomenclature alk ane * anal (but see also common/familiar names) Try to figure out the 3D organization of the molecule!
49 examples Nomenclature Paolo Sarti 2011 Department of Biochemistry Sapienza Heptanal Propanal 2-methyl-butanal 3,4-di-methyl-heptanal 2,2,4 tri-methyl-pentane OK
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