1. Aldehydes and ketones

2. Learning Objectives Aldehydes and ketones
Chapter eight introduces carbonyl compounds and reactions that involve a nucleophilic attack at the carbonyl carbon in addition to the other topics.
By the end of this chapter the student will:
Know the structural differences between aldehydes and ketones
Know how to draw aldehydes and ketones
know the common and IUPAC nomenclature of aldehydes and ketones
Know the physical properties of aldehydes and ketones
Know how to synthesize an aldehyde or a ketone from a compound without that
functionality.
Know the different nucleophilic attack reactions at the carbonyl carbon and the specific products formed in each case.

3. Nomenclature * Aldehyde
1] Ald. up to 4 carbons their common name after their acids to which they related.
2] IUPAC NAMES by replacing e(from alkane) by –al.
3] Carbon of ald. Always No. 1 (not appear in the name).

4. Nomenclature
1] IUPAC system: Select the longest continuous carbon chain that contains the C=O group and replace the ending by the suffix al.
Pentanal
Heptanal
3-Ethyl -heptanal
2] The CHO group is assigned the number 1 position and takes precedence over other functional groups that may the present such as –OH, C=C for example
2- pentenal
5-Chloro-3-hydroxyheptanal

5. Butyraldehyde
Propionaldehyde
Acetaldehyde
Formaldehyde
Common
Butanal
Propanal
Ethanal
Methanal
IUPAC
2-Butenal
4-Hydroxybutanal
2-ChloroPropanal

6. Nomenclature: 4] Substituted on ald. (OH > C=C or CC )
ClCH2CH2CH2CH2CHO CH3CH2CH=CHCHO
pent 2-en-1-al
5-Chloro pentanal
CH3CHOHCHClCH2CHO
3-Chloro-4-hydroxy pentanal

7. 5] Aromatic aldehyd derivatives of simplest aromatic (bezald.)

8. P-Methoxybenzaldehyde
3]Aromatic aldehydes are usually designated as derivatives of the simplest aromatic aldehyde, Benzaldehyde.
Benzaldehyde
o-Hydroxybenzaldehyde
Salicylaldehyde
P-Methoxybenzaldehyde
p-Nitrobenzaldehyde
Anisaldehyde

9. * Ketones
1) Simple by alkyl substituent and word ketone

10. Ketones: Structure And Nomenclature
General formula: RCOR’ (R and R’=alkyl or aryl)
IUPAC system
1] longest cont. chain with C=O , replace the ending –e by the suffix –one (Ketone). The chain is numbered in such a way as give the lowest number to the C=O group
1-Cyclopentylpropanone Ethyl-2-hydroxycyclohexanone Oxohexanal

11. Aldehydes and ketones
IUPAC Nomencalture :
Select the longest continuous carbon chain that contains the C=O group to get the name of the parent hydrocarbon, then replace the ending e by the suffix –one
The chain is numbered in such a way as give the lowest number to the C=O group.
The prefix of oxo is used if there are higher ranking functional groups present.

12. CH3CH2COCH3 CH3COCH2CH2CH2CH3
2) complicated ketones by IUPAC by replacing (e) by(-one) (in longest cont. chain with C=O) ket. Take lower no.
CH3CH2COCH CH3COCH2CH2CH2CH3
Butanone Hexanone
CH3CH2COCH2CH2CH CH3CH2CHClCOCH2CH3
3-hexanone chloro-3-hexanone
CH3CH2CH=CHCOCH3
3-hexene-2-one

13. 2]Common name: listing the alkyl substitutents attached to the carbonyl group, followed by the word ketone
Diphenyl ketone
Benzophenone
Methyl vinyl ketone
Methyl phenyl ketone
Acetophenone
Dimethyl Ketone
Acetone
Common
Diphenylmethanone
3-Buten-2-one
Phenyl ethanone
Propanone
IUPAC

14. KETONES:STRUCTUR AND NOMENCLATURE
Aldehydes and ketones
KETONES:STRUCTUR AND NOMENCLATURE
General formula: RCOR’ (R and R’=alkyl or aryl)
Common names of ketones derived by listing the alkyl substituents attached to the carbonyl group in alphabetical order, followed by the word ketone.
When a complex molecules contains more than one of functional groups, an order of precedence is used to determine the name.
The functional group priority order in nomenclature system is as following:
Acid and derivatives > aldehyde > ketone > alcohol > amine > alkene > alkyne > ether

15. Aldehydes and ketones
Propanone Phenyl ethanone Buten-2-one Diphenylmethanone
Cyclopentylpropanone Ethyl-2-hydroxycyclohexanone Oxohexanal

16. 3) If position of C=O not clear no. is needed for no.

17. Physical Properties OF Aldehydes And Ketones
The carbonyl group is polar; with a partial negative charge on oxygen atom, and partial positive charge on carbon atom.
Because the polarity of the carbonyl group, aldehydes and ketones are polar compounds.
1) Boiling and melting points
Higher melting and boiling points compared to analogous alkanes due to they show dipole-dipole attractions.
These attractions although important, are not as strong as interactions due to hydrogen bonding as a result, the boiling points of aldehydes and ketones are higher than those of non polar alkanes, but lower than those of alcohols whose molecules are connected together by H-bonds.

18. Aldehydes and ketones
2) Solubility
Lower aldehydes and ketones are are more soluble than alkanes but less soluble than alcohols in aqueous media

19. Preparation of Aldehydes & ketones
1] Oxidation of 1& 2 alcohol :
2] Ozonolysis of alkenes:

20. Preparation of Aldehydes & ketones
3] Hydration of alkynes:

21. 4] Friedel Craft acylation:

22. Reactions of Aldehydes and ketones
Nucleophilic addition Reactions
1] Addition of metal hydrides( formation of alcohol)

23. Reactions of Aldehydes and ketones

24. 2] Reactions with Grignard reagent:

25. CON’T
Addition of RMgX to formaldehyde gives 1◦ alc.
Addition of RMgX to any other aldehyde gives 2◦ alc.
Addition of RMgX to ketones gives 3◦ alc.

26. 3]Addition of alkynide ions: [R-C≡C-]

27. 4]Addition of hydrogen cyanide (cyanohydrins formations):

28. +

29. 5] Addition of alcohols Ald+ alcohol hemiacital Ket+ alcohol hemiketal
a) Hemiacitals formation
b) Hemiketals formation

30. c) Acetal formation:

31. d) Ketal formation:

32. 6] Tollens’ Test
Tollens’ reagent oxidizes an aldehyde into the corresponding carboxylic acid.  The reaction is accompanied by the reduction of silver ions in Tollens’ reagent into metallic silver, which, if the test is carried out in a clean glass test tube, forms a mirror on the test tube.
Ketones are not oxidized by Tollens’ reagent, so the treatment of a ketone with Tollens’ reagent in a glass test tube does not result in a silver mirror.

33. 7] Addition of ammonia and it's derivatives

34. Reduction of oxime O
8] Iodoform reaction

35. 8]Aldol condensation:
Aldehydes
Ketones

36. CON’T

37. CON’T

38. 1- The correct name of the following compound is:
Aldehydes and ketones
Exercises
1- The correct name of the following compound is:
A) 3-hydroxyhexanal
B) 3-hydroxy-4-hexenal
C) 4-hydroxy-5-hexenal
D)3-hydroxy-1-hexenal
2- The structure of Acetal is:

39. A) Oxime B) Phenylhydrazone C) Imine D) Hemiacetal
Aldehydes and ketones
3- Reaction of phenyhydrazine with carbonyl compounds (aldyhydes or ketones) gives:
A) Oxime B) Phenylhydrazone C) Imine D) Hemiacetal
4 - Which of the following compounds has the highest boiling point?

40. 7. What is the best reagent(s) to do the following conversion:
5. What is the IUPAC name of the following compound:
6. What is the correct structure for 2-Hydroxyacetophenone:
7. What is the best reagent(s) to do the following
conversion:
8. What is the product of the following reaction:

41. 9. What is the major product of the following reaction