Carbonyl

1. Carbonyl

2. Definition O • a CARBONYL GROUPis a functional group found in organic compounds composed of a Carbon atomdouble - bonded to an oxygen atom. ═ C

3. Family Under CARBONYL GROUP • Aldehyde • Ketone • Carboxylic Acid • Ester • Amide

4. Aldehyde

5. Definition • A compound containing a CARBONYL group bonded to a hydrogen.

6. Preparation

7. Natural Sources

8. O ║ C – H benzaldehyde

9. O ║ CH ═ CH – C – H cinnamaldehyde

10. O ║ C – H vanillin O – CH3 OH

11. CH3 CH3 O ║ CH3 – C = CH – CH2 –CH2 – C = CH – C – H Citral

12. Synthetic Sources

13. Oxidation 1ᵒ Alcohol gen. formula 1ᵒ Alcohol ---→ Aldehyde + H2O Hydration of Alkynes gen. formula Alkynes + H2O ---→ Aldehyde

14. Uses

15. Preservatives & Indus. Solvent

20. Adhesive additives

22. Medicine & Supplements

25. Food & Sweets

28. Plastics

30. Physical Properties

31. uniqueness ofAldehyde • CARBONYL groups of aldehydes give them sufficient POLARITY. • That makes their boiling points higher than those of non – polar organic compounds. • But lower compares to alcohol • Because no HYDROGEN bonding occurs in ALDEHYDES.

32. Table of Comparisons Therefore, boiling points of ALDEHYDES are lower than ketone and alcohol but higher compare to alkane.

33. Nomenclature

34. Things 2 remember

35. IUPAC RULES • IUPAC rule in naming ALDEHYDES follows the usual pattern. • The longest chain carrying the ALDEHYDE functional group is considered the parent structure and named by replacing the – e – of the corresponding ALKANE by – al – . • The position of a substituent is indicated by number, the CARBONYL carbon always being considered as C – 1.

36. COMMON Naming • Are derived from D’ names of the corresponding CARBOXYLIC ACIDS by replacing by replacing – ic – acid by ALDEHYDE. • Branched chain ALDEHYDES are named as derivatives of straight – chain aldehydes. • To indicate D’ point of attachment, the GREEK letters, α -, β -, γ -, δ -,ε -, ζ -, η -, θ -, ι -, κ, etc., are used; • The α – carbon is the one bearing the ALDEHYDE group.

37. EXAMPLEs: O ║ H – C – H methanal formaldehyde O ║ CH3 – C – H ethanal acetaldehyde

38. EXAMPLEs: O ║ CH3 – CH2 – CH2 – C – H butanal butyraldehyde O ║ CH3 – (CH2)5 – C – H heptanal enanthaldehyde

39. EXAMPLE: CH3 3HC O ║ CH3 – C – CH2 – CH2 – C – C – H CH3 CH3 2,2,5,5 – tetramethylhexanal α,α,δ,δ – tetramethylcaproaldehyde

40. EXAMPLE: O ║ C – H CH3 – CH2 – CH – CH2 – CH3 2 – ethylbutanal α– ethylbutyraldehyde

41. EXAMPLE: O ║ NO2 CH3 – CH – C – CH2 – C – H OH CH3 4 – hydroxy – 3 – methyl – 3 – nitropentanal γ – hydroxy – β – methyl – β – nitrovaleraldehyde

42. EXAMPLE: 3HC – 2HC CH2 –CH3 O ║ CH3 – (CH2)3 – C – C – (CH2)2 – C – H 3HC CH3 4,5 – diethyl – 4,5 – dimethyl – nonanal γ,δ – diethyl – γ,δ – dimethyl – pelargonaldehyde

43. EXAMPLE: H H OH H O ║ CH2 – C – C – C – C – C – H OH OH OH H OH 2,3,4,5,6 – pentahydroxyhexanal α,β,γ,δ,ε – hydroxycaproaldehyde GLUCOSE

44. GLUCOSE

45. EXAMPLEs: O ║ CH3 – CH ═ CH – CH2 – C – H 3 – pentenal CH3 CH3 O ║ CH3 – C = CH – CH2 –CH2 – C = CH – C – H 3,7 – dimethyl– 2,6 – octadienal CITRAL

46. EXAMPLE: O ║ C – H CH2 CH3 – (CH2)3 – C – (CH2)4 –CH ═ CH2 CH2 – CH3 3 – butyl – 3 – ethyl – 8 – nonenal

47. O ║ EXAMPLEs: CH3 – C ≡ C – CH ═ CH – CH2 – C – H 3 – heptenal – 5 – yne 3 – ene – 5 – heptynal 3 – hepten – 5 – yne – al CH2 – (CH2)3 – C ≡ C – CH – (CH2)2 – CH3 Cl O ║ C – H 8 – chloro – 2 – propyl – 3 – octynal

48. EXAMPLEs: O ║ C – H cyclohexanal cyclohexanecarbaldehyde O ║ C – H 3 – hydroxycyclopentanal HO γ – hydroxycyclopentanecarbaldehyde

49. EXAMPLEs: OH 4 – hydroxy – 2 – cyclobutenal O ║ C – H δ – hydroxycyclobutenecarbaldehyde 2 – cyclopropynal O ║ C – H cyclopropynecarbaldehyde

50. EXAMPLEs: O ║ C – H benzaldehyde O ║ C – H 3HC 3 – methyl – 5 – nitrobenzaldehyde γ – methyl – ε - nitrobenzaldehyde NO2