Chemistry 121(V84) Winter 2016
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1 Chemistry 121(V84) Winter 2016 Introduction to Organic Chemistry and Biochemistry Instructor Dr. Upali Siriwardane (Ph.D. Ohio State) Office: 311 Carson Taylor Hall ; Phone: ; Contact me trough if you have questions Online Tests on Following days June 17, 2016: Test 1 (Chapters 12-13) July 8, 2016 : Test 2 (Chapters 14-16) July 27, 2016 : Test 3 (Chapters 17-19) August 10, 2016 : Test 4 (Chapters 20-22) August 10, 2016: Make Up Exam: Chapters 12-22) 1-1
2 Chapter 15: Aldehyde and Ketones 15.1 The Carbonyl Group, Compounds Containing a Carbonyl Group, The Aldehyde and Ketone Functional Groups, Nomenclature for Aldehydes, Nomenclature for Ketones, Isomerism for Aldehydes and Ketones, Selected Common Aldehydes and Ketones, Physical Properties of Aldehydes and Ketones, Preparation of Aldehydes and Ketones, Oxidation and Reduction of Aldehydes and Ketones, Reaction of Aldehydes and Ketones with Alcohols, Formaldehyde-Based Polymers, Sulfur-Containing Carbonyl Groups,
3 Carbonyl Group 1-3
4 Simplest Aldehyde 1-4
5 Common Names of Aldehyde and Ketones Aldehydes: Fomaldehyde: HCHO Acetaldehyde: CH 3 CHO Propionaldehyde: CH 3 CH 2 CHO Butyraldehyde: CH 3 CH 2 CH 2 CHO Valeraldehyde: CH 3 CH 2 CH 2 CH 2 CHO Ketones: Acetone: CH 3 COCH 3 Methyl ethyl ketone CH 3 CH 2 COCH 3 Butyl propyl ketone CH 3 CH 2 CH 2 CH 2 COCH 2 CH 2 CH 3 1-5
6 IUPAC Nomenclature of Aldehyde and Ketones The IUPAC system deals with functional groups two different ways. Modification of the hydrocarbon name to indicate the presence of a functional group. aldehyde, -CHO Ketones -RCOR use -al ending. use -one ending. 1-6
7 IUPAC Nomenclature of Aldehyde and Ketones The IUPAC system deals with functional groups two different ways. Modification of the hydrocarbon name to indicate the presence of a functional group. aldehyde, -CHO Ketones -RCOR use -al ending. use -one ending. 1-7
8 Example C - C - C - C - CHO Base contains 5 carbon - aldehyde name is pentane - remove -e and add -al C - C - C - C - CO-C-C Base contains 7 carbon - aldehyde name is heptane - remove -e and add -one 3-heptanone 1-8
9 Physical Properties of Aldehydes and ketones Aldehyde and ketones can only make dipole-dipole attraction. BP and MP are lower than alcohols, higher than hydrocarbons and ether with comparable carbon numbers 1-9
10 Bonding Characteristics of Aldehydes Ketones Both aldehydes and ketones contain a carbonyl functional group. A carbonyl group is an carbon atom double-bonded to an oxygen atom. The structural representation for a carbonyl group is Carbon-oxygen (C=O) and carbon-carbon (C=C) double bonds differ in a major way. A carbon oxygen double bond is more polar 1-10
11 Physical properties of aldehydes and ketones. 1-11
12 Nomenclature Functional Grou p Su ffix Prefix Carb oxyl Ald ehyde -oic acid -al oxo- Ketone -one oxo- Example of When the Functional Group Has a Lower Priority 3-Oxopropan oic acid 3-Oxobutanoic acid O H O COOH COOH Alcoh ol -ol hydroxy- 4-Hydroxybutan oic acid HO COOH Amino -amine amino- 3-Aminobutan oic acid NH 2 COOH Su lfh ydryl -thiol mercapto- 2-Mercaptoethanol HS OH 1-12
13 Name the Aldehyde 2,4-dimethylpentanal 1-13
14 1. Assign the type of organic compound with following general condensed (structural formula. 1-14
15 2. Names (common/iupac)of following aldehydes and ketones. a) b) c) d) e) f) Chemistry 121, Summer g) 2016, LA Tech h) 1-15
16 Nomenclature O H 3-Methylbutan al O H 2-Propen al (Acrolein) O (2E)-3,7-D imeth yl-2,6-octad ienal (Geran ial) H CHO HO 4 1 CHO Cyclopen tanecarb aldehyde trans-4-hyd roxycyclohexan ecarbald ehyde O O O O 5-Methyl-3- hexanone 2-Methylcycloh exanone Acetophenone Benzoph enone 1-16
17 3. Draw the condensed formula of following aldehydes and ketones : a) acetaldehyde/ ethanal b) ethyl methyl ketone c) 3-methyl-2- pentanone d) isopropyl methyl ketone e) 2- methylbutanal f) 5-methyl-3- hexanone g) benzophenone h) acetophenone 1-17
18 Addition reactions of als & ones Hemiacetal or hemiketal formation 1-18
19 Hemiacetal form of cyclic sugars 1-19
20 4. Identify each of the following compounds as a hemiacetal, hemiketal, acetal, or ketal: a) b) c) d) e) f) 1-20
21 Important Aldehydes Methanal or formaldehyde Ethanal or acetaldehyde 2-Propanone or acetone 2-Butanone or methyl ethyl ketone Oil of almonds or benzaldehyde Oil of Cinnamon or cinnamaldehyde Oil of vanilla beans or vanillin Mushroom flavoring or 2-octanone Oil of lemongrass or citral: 1-21
22 Bakelite 1-22
23 Preparation of Aldehydes: Partial oxidation of primary alcohols with H 2 CrO 4 : 1-23
24 Preapration of ketones: Oxidation of secondary alcohols with KMnO 4, or H 2 CrO
25 Oxidation of alcohol 1-25
26 Oxidation of Alcohols to oxidize a 1 alcohol to an aldehyde, use PCC CrO 3 + HCl + N Pyridine CrO 3 Cl - N+ H Pyridiniu m chloroch romate (PCC) PCC oxidation of geraniol gives geranial Geraniol OH PCC CH 2 Cl 2 Geranial O H Tertiary alcohols are not oxidized by either of these reagents; they are resistant to oxidation 1-26
27 Oxidation of alcohol 1-27
28 a) 5) Which alcohol would you oxidize to produce each of the following compounds? b) c) d) 1-28
29 6) Preparation of adehydes and ketones a) Control oxidation of 1ry alcohol b) Complete oxidation of 1 ry alcohol 1-29
30 6) Preparation of adehydes and ketones c) Oxidation of 2 ry alcohol d) Oxidation of 3 ry alcohol No Reaction 1-30
31 Chemical Reactions of Aldehydes and Ketone 1) Combustion: Alkenes are very flammable and the combustion products are carbon dioxide and water. 2) Addition Reactions: Atoms or group of atoms are added to each a carbon oxygen double bond. Two different reactants are involved. a) hemi-acetal or hemi-ketal formation: Addition of Alcohols: -OR group of the R-OH is added to the C atom and H of the ROH is added to O atom. b) Aacetal or ketal formation : Another or second ROH is reacted in a substitution reaction to replace the H atom of the -OH group of the hemi-acetal or hemi-ketal and water molecule is produced. O: both reactants (H-X (X= Cl, OH)) and the alkene need to be asymmetric 3) Oxidation Reactions: only aldehydes are oxidized to carboxylic acids. 4) Reduction Reactions: both aldehydes and ketones are reduced to alcohols by taking H from the reducing agents. 1-31
32 Chemical Reactions of Aldehydes and Ketone a) hemi-acetal or hemi-ketal formation: Addition of Alcohols: -OR group of the R-OH is added to the C atom and H of the ROH is added to O atom. b) Aacetal or ketal formation : Another or second ROH is reacted in a substitution reaction to replace the H atom of the -OH group of the hemi-acetal or hemi-ketal and water molecule is produced. O: both reactants (H-X (X= Cl, OH)) and the alkene need to be asymmetric 1-32
33 Reduction of als & ones compounds to alcohols: 1-33
34 Redox Reactions Reduction Reactions: both aldehydes and ketones are reduced to alcohols by taking H from the reducing agents. a) LiAlH4 b) NaBH4 c) H 2 /Ni or Pt catalysts Oxidation Reactions: only aldehydes are oxidized to carboxylic acids. a) Jone s Reagent b) AgNO 3 /NH 4 OH (silver mirror test) c) CuSO 4 /Na 2 CO 3 /Citrate (Benedict s reagent) 1-34
35 Aldehyde and Ketone Reduction: To alcohols O C H 2, Ni OH C H NaBH 4 or LiAlH 4 then H
36 7) Complete the following reductions of aldehyde and ketones and identify the type of alcohols (1ry, 2ry and 3ry) produced. d) 1-36
37 Reduction of als & ones compounds to alcohols: 1-37
38 Addition reactions of als & ones Hemiacetal or hemiketal formation 1-38
39 Addition reactions of als & ones Hemiacetal or hemiketal formation 1-39
40 Hemiacetal form of cyclic sugars 1-40
41 Formation of Acetals and Ketals. 1-41
42 8) Complete the following formation reactions hemiacetal, hemiketal, acetal, or ketal: 1-42
43 Redox Reactions Reduction Reactions: both aldehydes and ketones are reduced to alcohols by taking H from the reducing agents. a) LiAlH4 b) NaBH4 c) H 2 /Ni or Pt catalysts Oxidation Reactions: only aldehydes are oxidized to carboxylic acids. a) Jone s Reagent b) AgNO 3 /NH 4 OH (silver mirror test) c) CuSO 4 /Na 2 CO 3 /Citrate (Benedict s reagent) 1-43
44 Chemical Reactions Oxidation of aldehyde. Benedict's Test for aldehydes: 1-44
45 Test for Urine Glucose: Benedict s Test 1-45
46 Tollen's Test: Oxidation of aldehyde. The commercial manufacture of silver mirrors uses a similar process. 1-46
47 9) Complete reactions of following aldehydes and ketones a) Tollen s Reagent: Silver mirror test: b) Benedict's test: 1-47
48 9) Complete reactions of following aldehydes and ketones c) Oxidation of aldehyde d) Cyclic hemi-acetal formation 1-48
49 Addition of HCN and H 2 O 1-49
50 Aldol Condensation In biological systems this reaction is catalysed by an enzyme named aldolase. 1-50
51 Keto & Enol tautomers keto form enol from 1-51
52 Keto & Enol tautomers in sugars aldehyde enol ketone 1-52
53 Addition reactions of als & ones Hemiacetal or hemiketal formation 1-53
54 Formation of Acetals and Ketals. 1-54
55 Hemiacetal form of cyclic sugars 1-55
Carbonyl Group. Chemistry 121(01) Winter Chapter 15: Aldehyde and Ketones. Chapter 15: Aldehyde and Ketones
Chemistry 121(01) Winter 2012 Introduction to rganic Chemistry and Biochemistry Instructor Dr. Upali Siriwardane (Ph.D. hio State) E-mail: upali@chem.latech.edu ffice: 311 Carson Taylor Hall ; Phone: 318-257-4941;
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