1-1 Chemistry 121, Winter 2012, LA Tech Introduction to Organic Chemistry and Biochemistry Instructor Dr. Upali Siriwardane (Ph.D. Ohio State) Office: 311 Carson Taylor Hall ; Phone: ; Office Hours: MTW 9:00 am - 11:00 am; TR 9: :00 am & 1:00-2:00 pm. December 16, Test 1 (Chapters 12-13) January 20 Test 2 (Chapters 14-16) February 6 (Chapters 17-19) February 27, (Chapters 20-22) February 28, 2012, Make Up Exam: Bring Scantron Sheet 882-E Chemistry 121(01) Winter 2012

1-2 Chemistry 121, Winter 2012, LA Tech Chapter 15: Aldehyde and Ketones Sections

1-3 Chemistry 121, Winter 2012, LA Tech Chapter 15: Aldehyde and Ketones 15.1 The Carbonyl Group 15.2 Structure of Aldehydes and Ketones 15.3 Nomenclature for Aldehydes 15.4 Nomenclature for Ketones 15.5 Isomerism for Aldehydes and Ketones 15.6 Selected Common Aldehydes and Ketones 15.7 Physical Properties of Aldehydes and Ketones 15.8 Preparation of Aldehydes and Ketones 15.9 Oxidation and Reduction of Aldehydes and Ketones Reaction of Aldehydes and Ketones with Alcohols

1-4 Chemistry 121, Winter 2012, LA Tech Carbonyl Group

1-5 Chemistry 121, Winter 2012, LA Tech Structure the functional group of an aldehyde is a carbonyl group bonded to a H atom the functional group of a ketone is a carbonyl group bonded to two carbon atoms

1-6 Chemistry 121, Winter 2012, LA Tech 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. al aldehyde, -CHOuse -al ending. one Ketones -RCOR’ use -one ending.

1-7 Chemistry 121, Winter 2012, LA Tech Example C - C - C - C - CHO Base contains 5 carbon -aldehyde name is pentane -e -al -remove -e and add -al C - C - C - C - CO-C-C Base contains 7 carbon -aldehyde name is heptane -e -one -remove -e and add -one 3-heptanone

1-8 Chemistry 121, Winter 2012, LA Tech Nomenclature

1-9 Chemistry 121, Winter 2012, LA Tech Nomenclature

1-10 Chemistry 121, Winter 2012, LA Tech Name the Aldehyde 2,4-dimethylpentanal

1-11 Chemistry 121, Winter 2012, LA Tech Common Names 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 CHOKetones: 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

1-12 Chemistry 121, Winter 2012, LA Tech Simplest Aldehyde

1-13 Chemistry 121, Winter 2012, LA Tech 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:

1-14 Chemistry 121, Winter 2012, LA Tech Bakelite

1-15 Chemistry 121, Winter 2012, LA Tech Preapration of Aldehydes: Partial oxidation of primary alcohols with H 2 CrO 4 :

1-16 Chemistry 121, Winter 2012, LA Tech Preapration of ketones: Oxidation of secondary alcohols with KMnO 4, or H 2 CrO 4

1-17 Chemistry 121, Winter 2012, LA Tech Oxidation of alcohol

1-18 Chemistry 121, Winter 2012, LA Tech Oxidation of alcohol

1-19 Chemistry 121, Winter 2012, LA Tech Physical properties of aldehydes and ketones.

1-20 Chemistry 121, Winter 2012, LA Tech Chemical Reactions Oxidation of aldehyde. Benedict's Test for aldehydes:

1-21 Chemistry 121, Winter 2012, LA Tech Test for Urine Glucose: Benedict’s Test

1-22 Chemistry 121, Winter 2012, LA Tech Oxidation of aldehyde. The commercial manufacture of silver mirrors uses a similar process. Tollen's Test:

1-23 Chemistry 121, Winter 2012, LA Tech Reduction of als & ones compounds to alcohols:

1-24 Chemistry 121, Winter 2012, LA Tech Addition reactions of als & ones Hemiacetal or hemiketal formation

1-25 Chemistry 121, Winter 2012, LA Tech Hemiacetal form of cyclic sugars

1-26 Chemistry 121, Winter 2012, LA Tech Formation of Acetals and Ketals.

1-27 Chemistry 121, Winter 2012, LA Tech Addition of HCN and H 2 O

1-28 Chemistry 121, Winter 2012, LA Tech Aldol Condensation In biological systems this reaction is catalysed by an enzyme named aldolase.

1-29 Chemistry 121, Winter 2012, LA Tech Keto & Enol tautomers keto form enol from

1-30 Chemistry 121, Winter 2012, LA Tech Keto & Enol tautomers in sugars aldehyde enol ketone