Organic Compounds Containing Oxygen
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1 BI-GANI EMISTY (rganic hemistry for Biology Students) (SQBS 1603) rganic ompounds ontaining xygen Dr Nik Ahmad Nizam Bin Nik Malek, BSc (Ind. hem.)(utm), MSc (hem)(utm), PhD (hem)(utm), A.M.I. Senior Lecturer, Department of Biotechnology and Medical Engineering Faculty of Biosciences and Medical Engineering
2 Physical properties of the alkanes Alkanes are insoluble in water The alkanes have few direct roles in biological systems Biological systems are aqueous (water based) Adding functional groups 2
3 What is functional group? Molecules possessing the same functional group belong to the same family of organic compounds. The chemical components that are added to the simple skeleton of an organic compound. To generate chemical diversity and functionality. ydrocarbon Groups containing oxygen Groups containing nitrogen Groups containing phosphorus and sulfur 3
4 Amines Amides Thiols phosphate Alcohol functional groups Esters Ethers Ketone Aldehyde arboxylic acids
5 Functional groups Biological importance of functional group Functional group Biological importance Alcohol Ethers Ketone Aldehyde arboxylic acids Ester Amines Amides Thiol Phosphate Lipids, carbohydrates Archael plasma membranes Metabolic intermediates educing sugars such as glucose Lipids, proteins Bacterial and eukaryotic plasma membranes Proteins, nucleic acids DNA and NA Proteins, nucleic acids DNA and NA Protein structure, Energy metabolism ATP, DNA 5
6 Functional groups hemical class Group Formula Groups containing oxygen Structural Formula Prefix Suffix Example Alcohol ydroxyl hydroxy- -ol Methanol Ketone arbonyl ' keto-, oxo- -one Methyl ethyl ketone (Butanone) Aldehyde Aldehyde aldo- -al Acetaldehyde (Ethanal)
7 Functional groups Groups containing oxygen hemical class Group Formula Structural Formula Prefix Suffix Example arboxylate (arboxylic acid) arboxyl arboxy- -oic acid Acetic acid Esters Ester ' alkyl alkanoate Ethyl butyrate (Ethyl butanoate) Ethers ether Di- -ether Diethyl ether 7
8 Functional groups Groups containing nitrogen hemical class Group Formula Structural Formula Prefix Suffix Example Dimethylamine Amines Amino N 2 2 N 3 N amino- -amine Acetamide Amide Amide N 2 N N 2 arboxamide- -amide
9 9 Functional groups Groups containing sulphur and phosporus hemical class Group Formula Structural Formula Prefix Suffix Example Thiol Sulfhydryl S Mercapto- Sulfanyl- -thiol Ethanathiol (Ethyl mercaptan) Glyceraldehyde 3-phosphate Phosphate phoshate P(=)() 2 phospho-
10 Alcohol Alcohol ydroxyl group : - functional group Generic formula: - General structure
11 Alcohol lassification ydroxyl group ' ' '' Primary (1 ) Secndary (2 ) Tertiary (3 ) 11
12 Naming Alcohols : 6 hexane hexanol Methyl at methyl-3-hexanol
13 Naming Alcohols Give the IUPA name of the following alcohol Methyl at : 6 cyclohexane cyclohexanol 3-methyl-cyclohexanol 13
14 Naming Alcohols -diol Ethanol IUPA name: 1,2-ethanediol or Ethane-1,2-diol ommon name: ethylene glycol 14
15 eactions of alcohol Dehydration xidation 15
16 Dehydration Loss of water ( 2 ) Elimination reaction Elements of the starting material are lost and a new multiple bond is formed 2 S is lost alkene
17 Dehydration Examples 2 S 4 2 Ethanol Ethene 2 S 4 2 yclohexanol yclohexene 17
18 Zaitsev rule Dehydration The major product in elimination is the alkene that has more alkyl groups bonded to it S Butan-2-ol But-1-ene S 4 3 Butan-2-ol But-2-ene Major product 18
19 xidation Primary (1 ) alcohols xidized to aldehydes () And further oxidized to carboxylic acids () [] [] alcohol aldehyde arboxylic acid 19
20 xidation Secondary (2 ) alcohols xidized to ketones ( 2 ) ' [] ' alcohol ketones 20
21 Tertiary(3 ) alcohols xidation They are not oxidized ' '' 21
22 Physical properties of alcohols 22 hydroxyl group oxygen + hydrogen highly electronegative atom polar molecules
23 Physical properties of alcohols hydroxyl group oxygen + hydrogen highly electronegative atom Strong non-covalent forces polar molecules hydrogen bonding Exhibit higher melting and boiling points than alkanes dipolar interaction dispersion forces soluble in water in small quantity 23
24 Physical properties of alcohols Ethanol Low electron density high electron density Electron pulls towards highly electronegative oxygen atom The distribution of electrons within the molecules is unequal The molecule is polar 24
25 Physical properties of alcohols hydrogen bonding 3 2 Ethanol is attracted to the water molecules through hydrogen bonds 25
26 Ether Alkoxy group : combination of an alkyl group and oxygen atom (alkyl + oxygen = alkoxy) Generic formula: -- Similar to alcohol (hydroxyl group), except that the atom is replaced with an alkyl group ydroxyl group Alkoxyl group ' 26
27 Ether groups are the same groups are different 27
28 Naming Ether Simple ethers: Usually assigned common names Methyl- Ethyl- Ethyl- Ethyl- Ethyl methyl ether (methoxy-ethane) diethyl ether (ethoxy-ethane) 28
29 Naming Ether More complex ethers: IUPA name Methoxy- Ethoxy- 29
30 Naming Ether nonane 3-ethoxy-nonane 3 2 Ethoxy- at position 3 30
31 Physical properties of ethers Presence of oxygen polar molecules 3 3 Two polar bonds 31
32 Aldehydes and Ketones arbonyl group arbonyl carbon Aldehyde Ketone 32
33 Aldehydes and Ketones Aldehyde Ketone 3 Acetaldehyde 3 3 Propan-2-one 33
34 IUPA name Naming aldehydes 4 butane butanal Methyl at 2 and 3 dimethyl ,3-dimethylbutanal 34
35 Simple aldehydes have common names that are widely used Examples: Naming aldehydes Formaldehyde 3 Acetaldehyde Benzaldehyde 35
36 Naming Ketones IUPA name 5 pentane pentanone methyl-2-pentanone arbonyl position 2 Methyl position 3 36
37 37 ommon names for ketones: 3 Naming both alkyl group on the carbonyl carbon. Arranging them alphabetically. Finally, adding the word ketone. 2 3 IUPA name: 2-butanone Naming Ketones methyl ethyl common name: Ethyl methyl ketone
38 Physical properties of aldehydes and ketones Presence of oxygen polar molecules Ether Aldehyde ketone 3 3 Two polar bonds - - Electrons pulled towards highly electrone gative oxygen atom.generating an uneven distribution of electron: polar molecule 38
39 eactions of aldehydes and ketones 1. xidation of aldehydes Aldehyde 2. eduction of aldehydes and ketones (addition reaction) [] arboxylic acid 39 X Y X Y
40 xidation of aldehydes Examples Butyraldehyde K 2 r Butyric acid ow about ketones? 3 2 K 2 r 7 No eaction 3 40 Butan-2-one
41 eduction of aldehydes and ketones (addition reaction) eduction Decrease in the number of - Increase in the number of - bonds The conversion of a carbonyl group (=) to an alcohol is a reduction. The starting material has more - bonds than the product X Y 41 X Y
42 eduction of aldehydes and ketones Aldehydes (addition reaction) educe to primary (1 ) alcohol Aldehyde [] primary alcohol 3 Acetaldehyde [] 3 Ethanol ( 3 2 ) 42
43 eduction of aldehydes and ketones (addition reaction) Ketones 43 educe to secondary (2 ) alcohol [] ' ' ketone [] Propan-2-one 3 Propan-2-ol Secondary (( 3 ) 2 )
44 Acetal formation Aldehydes and ketones undergo addition reaction with alcohols to form hemiacetals and acetals. '- ''- '' (or ) 2 S4 ' (or ) 2 S4 ' (or ) Aldehyde or ketone hemiacetal acetal 1 is bonded to: -ne group -ne group 1 is bonded to: -two group 44
45 Acetal formation Example 3 2 Ethanol S 4 Propionaldehyde Ethoxy-propan-1-ol hemiacetal 3 2 Ethanol 2 S ,1-Diethoxy-propane acetal 3 3 Propan-2-one 3 2 Ethanol 2 S Ethoxy-propan-2-ol hemiacetal 3 2 Ethanol 2 S ,2-Diethoxy-propane acetal 45
46 yclic hemiacetals 1 is bonded to: -ne group -ne group (or ) 1 is bonded to: -ne group -An group that is part of a ring 46
47 yclic hemiacetals Formation of cyclic hemiacetals Intramolecular reaction of a compound that contain both a hydroxyl group (-) and aldehyde or ketone ydroxy-pentanal
48 arboxylic Acids arboxyl group: ombining the hydroxyl and carbonyl. Generic formula: or 2 carbonyl hydroxyl 48
49 Naming arboxylic acids IUPA system suffix oic acid 6 hexane hexanoic acid methyl at position 4 and 5 4,5-dimethyl ,5-dimethylhexanoic acid
50 Naming arboxylic acids Many simple carboxylic acids are often referred to by their common names. Formic acid 3 Acetic acid IUPA name: methanoic acid IUPA name: ethanoic acid Benzoic acid IUPA name: benzenecarboxylic acid 50
51 Physical properties of carboxylic acids 2 oxygen atoms 2 very electronegative atoms attach with each other 51
52 Physical properties of carboxylic acids Polarity? Dipolar interaction? ydrogen bonding between molecules of same compound? ydrogen bonding with water? Solubility in water? Boiling point? 52
53 Physical properties of carboxylic acids Presence of oxygen + hydrogen (carbonyl and hydroxyl group) polar molecules 53 ydrogen bonding between molecules of same compound
54 Physical properties of carboxylic acids ydrogen bonding with water? Solubility in water? 54
55 The acidity of carboxylic acids 2 3 carboxylic acid carboxylate anion 3 Acetic acid 2 3 Acetic acid anion 3 acetate 55
56 eaction with bases 3 Acetic acid Na 3 Na + Sodium acetate - arboxylate anions 56
57 arboxylate anions exanoic acid Na or K Na+ or K + arboxylate anions: sodium or potasium hexanoate Name of the metal cation (e.g: sodium) + Parent (e.g. hexane) + -ate (suffix) 57
58 onversion of carboxylic acids to esters and amides Formation of ester -' alcohol 2 S 4 - arboxylic acid ester Formation of amide -N 2 ammonia N 2 - arboxylic acid amide 58
59 Esters A modified carboxyl group Generic formula: arboxylic acid and combined to form 2 ' alcohol 59 ' '
60 IUPA system suffix ate Two parts Naming esters 1. Name the acyl group (-) by changing the ic ending of the parent carboxylic acid to the suffix ate. 2. Name the group bonded to the oxygen atom as an alkyl group. Acyl group ' Alkyl group 60
61 Naming esters 4 butanoic acid butanoate = methyl Methyl butanoate 61
62 Physical properties of esters arboxylic acid ester 62
63 Physical properties of esters Polarity? Dipolar interaction? ydrogen bonding between molecules of same compound? ydrogen bonding with water? Solubility in water? Boiling point? 63
64 Ester formation from carboxylic Substitution acids All acyl () compounds. Z -Y Y -Z Z =, ', N' 2 Y replaces Z Y=, ', N 2 ' 64
65 Fischer esterification Ester formation Treatment of carboxylic acid () with an alcohol ( ) in the presence of an acid catalyst forms an ester ( ). example Acetic acid ethyl acetate 65
66 EFEENES rowe, J., Bradshaw, T. and Monk, P. (2006), hemistry for the Biosciences: The Essential oncepts, xford University Press, xford. orton,.., Moran, L.A., Scrimgeour, K.G., Perry, M.D. and awn J.D. (2006). Principles of Biochemistry, 4 th Edition. Pearson International Edition. Smith, J.G. (2010). General, rganic and Biological hemistry. McGraw-ill igher Education. Denniston, K.J., Toping, J.J. and aret,.l. (2008). General, rganic and Biochemistry, 6 th edition. McGraw-ill igher Education.
67 MY PFILE Dr Nik Ahmad Nizam Bin Nik Malek, BSc (Ind. hem.)(utm), MSc (hem)(utm), PhD (hem)(utm), A.M.I. Senior Lecturer, Department of Biotechnology and Medical Engineering, Faculty of Biosciences and Medical Engineering, Universiti Teknologi Malaysia. Website:
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