Classification of oxo compounds, bonding system of oxo group, the stability of the C = O bond. Physical properties. The acid-base properties of

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1 Classification of oxo compounds, bonding system of oxo group, the stability of the C = O bond. Physical properties. The acid-base properties of aldehydes and ketones, keto-enol tautomerism. Nucleophilic addition reactions with O-, S-, N- and C-nucleophiles, the reversible nature of the addition. Condensation reactions. Oxidation and reduction reactions. The reactions of -carbon; aldol dimerization, -halogenation. The nucleophilic addition reactions of,b-unsaturated oxo compounds. Preparation of aldehydes and ketones.

2 Classification of compounds with C=O bond Aldehydes and ketones contain an acyl group bonded either to hydrogen or to another carbon. Functional group: acyl group Classification 1. according to functional group 3. according to the attached hydro carbonyl chain - aldehydes (RCHO) - aliphatic or aromatic / heteroaromatic - ketones (RR 1 CO) - non-cyclic or cyclic 2. numbers of functional groups - monoaldehyde/ketone - dialdehyde/diketone - polyaldehyde/polyketone cyclic aldehyde cyclic ketone non-cyclic ketone

3 Nomenclature 1. Aldehydes Only substitutive nomenclature, NO functional class nomenclature - al suffix, prefix: formyl if there is a group with higher priority. Note: there is no location number because the formyl group (-CHO, NOT -COH!!!) can be only the end of the chain 3 formyl groups: main chain + polyaldehyde suffix with location numbers Similar if the aldehyde is cyclic!

4 Nomenclature 2. When a formyl group (-CHO) is attached to a ring, the ring name is followed by the suffix -carbaldehyde. Certain common names of familiar aldehydes are acceptable as IUPAC names. A few examples include

5 Nomenclature 3. More examples Semi-trivial nomenclature of aldehydes the Latin name of the corresponding carboxylic acid + "aldehyde" ending Eg: acidum aceticum acetaldehyde And common names

6 Nomenclature Ketones Both substitutive and the functional class nomenclature! Substitutive ~: -one suffix, prefix: oxo if there is a group with higher priority. If there are more oxo groups: location numbers and multiplier With ketones, the -e ending of an alkane is replaced by -one in the longest continuous chain containing the carbonyl group. The chain is numbered in the direction that provides the lower number for this group. Functional class ~: related hydrocarbons + ketone end Although substitutive names of the type just described are preferred, the IUPAC rules also permit ketones to be named by functional class nomenclature. The groups attached to the carbonyl group are named as separate words followed by the word ketone. The groups are listed alphabetically.

7 Nomenclature 5. More examples Semi-trivial and common names Fuctional groups

8 Bonding system of C=O bond Heteronuclear + bond system with sp 2 pillar atoms similarity to alkenes Difference to alkenes: different EN strongly polarised bond Approx.: 40-50% ionic bond Dipole molecules (μ = D) C=O double bond shorter and stronger bonds, planar trigonal arrangement (depending the size of the attached groups and nonbonding e-pairs d C=O ~0.121 nm d C-O = nm (EtOH, Me 2 O) Comparing bond energies (E) A C=O bond is stronger then C=C double bond and stronger then 2xC-O single bond!! Bond E (kj/mól) Bond E (kj/mól) Special thermodynamic stability Cleavage of C=O bond is not favoured CH 3 -CH CH 3 -OH 321 CH 2 =CH CH 2 =O 687 reversible Ad N reactions

9 Comparison of the stability of aldehydes and ketones - electron donating groups (alkyl) ketones are more stable than aldehydes Electronic effect of carbonyl group -I (inductive effect) and M (mesomeric effect) The p z orbital of the carbon is empty decreased e-density (Important!! M if only a neighbouring -system is exists!) Physical properties if C=O compounds 1. Melting point, boiling point Mp ( o C) Mp ( o C) HCHO Mp: Homologous series exists, but there MeCHO is no characteristic path EtCHO -81 Me 2 CO -95 PrCHO -99 MeCOEt -87 Bp values of different analogues Bp ( o C) Bp ( o C) HCHO MeCHO EtCHO 50 Me 2 CO 56 PrCHO 76 MeCOEt 80 BuCHO 103 MeCOPr EtCOEt BuCHO -92 MeCOPr EtCOEt C 5 H 12 BuCl Et 2 O PrCHO EtCOMe BuOH Mw Bp ( o C) Bp: dipole-dipole interactions are stronger compare to R-Cl / R 2 O But weaker than H-bond interactions (alcohols)!!

10 2. Solubility in water determining factors: the stability of H-bonds S[g/mL] H-bridge acceptor character!! Generally C 5, C 6 significant solubility in water and also in organic solvents Typically: dipolar aprotic solvents Chemical properties of C=O compounds 1. Acid-base properties 1.1. Acidity: carbonyl group I, M effect -H is easily can be cleaved! The carbonyl group acts as a powerful electron-withdrawing substituent, increasing the acidity of protons on the adjacent carbons. (like an acid: C-H acidity) Delocalized (stable) electron system This proton is far more acidic than a hydrogen in an alkane. Under basic condition the -C become nucleophilic C-C bond formation (see latter)

11 C-C bond formation reactions Malonic ester - and acetoacetic ester synthesis: important synthesis methods Based on the CH acidity and the easy decarboxylation of b dicarboxylic compounds Malonic ester synthesis diethyl malonate or malonic acid's diethyl ester Synthesis of 2-monosubstituted or 2,2-disubstituted acetic acid derivatives Possibilities: Synthesis of b- and g- oxo carboxylic acid derivatives

12 ethyl acetoacetate Acetoacetic ester synthesis Synthesis of 1-monosubstituted or 1,1-disubstituted derivatives of acetone Cyclic compound also can be formed if R-R 1 is cyclic Possibilities: Formation of b- and g- diketones

13 BUT! ACIDs also can be prepared by acetoacetic ester synthesis using concentrated (cc.) base! 1.2. Basicity of carbonyl compounds reaction with Brönsted or Lewis acids Similar reactivity toward Lewis acids, too! Due to the two mesomeric structures stability is considerable! acid catalysed reactions are important (enol formation)

14 1.3. Keto-enol tautomerism Aldehydes and ketones are in equilibrium with their enol isomers. Enols are related to an aldehyde or a ketone by a proton-transfer equilibrium known as keto enol tautomerism. (Tautomerism refers to an interconversion between two structures that differ by the placement of an atom or a group. The keto and enol forms are constitutional isomers. Using older terminology they are referred to as tautomers of each other. The rate of enolization is catalyzed by acids

15 The amount of enol present at equilibrium, the enol content, is quite small for simple aldehydes and ketones. The equilibrium constants for enolization, as shown by the following examples, are much less than 1. In these and numerous other simple cases, the keto form is more stable than the enol by some kj/mol (11 14 kcal/mol). The chief reason for this difference is that a carbon oxygen double bond is stronger than a carbon carbon double bond.

16 With unsymmetrical ketones, enolization may occur in either of two directions: The ketone is by far the most abundant species present at equilibrium. Both enols are also present, but in very small concentrations. It is important to recognize that an enol is a real substance, capable of independent existence. An enol is not a resonance form of a carbonyl compound; the two are constitutional isomers of each other. STABILIZED ENOLS Certain structural features can make the keto enol equilibrium more favorable by stabilizing the enol form. Enolization of 2,4-cyclohexadienone is one such example: The enol is phenol, and the stabilization gained by forming an aromatic ring is more than enough to overcome the normal preference for the keto form.

17 A 1,3 arrangement of two carbonyl groups (compounds called b-diketones) leads to a situation in which the keto and enol forms are of comparable stability. methylene group flanked by the two carbonyls The two most important structural features that stabilize the enol of a b-dicarbonyl compound are (1) conjugation of its double bond with the remaining carbonyl group and (2) the presence of a strong intramolecular hydrogen bond between the enolic hydroxyl group and the carbonyl oxygen. In b-diketones it is the methylene group flanked by the two carbonyls that is involved in enolization. The alternative enol does not have its carbon carbon double bond conjugated with the carbonyl group, is not as stable, and is present in negligible amounts at equilibrium.

18 BASE-CATALYZED ENOLIZATION: ENOLATE ANIONS The proton-transfer equilibrium that interconverts a carbonyl compound and its enol can be catalyzed by bases as well as by acids. The key intermediate in this process, the conjugate base of the carbonyl compound, is referred to as an enolate ion, since it is the conjugate base of an enol. Protonation of this anion can occur either at the carbon or at oxygen. Protonation of the carbon simply returns the anion to the starting aldehyde or ketone. Protonation of oxygen produces the enol.

19 Conclusion Acid or base catalysis, equilibrium. Keto form is favoured (thermodynamic reason) except there is chance for conjugation or intramolecular H-bond Oxo Enol contant (%) Me 2 CO 2.5 x 10-4 Cyclohexanone 0.02 PhCH 2 COCH 3 3 MeCOCH 2 COOEt 8 MeCOCH 2 COMe 76 conjugation H-bond

20 electrophile sp 2 C Nu attack

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