14.1 Aldehydes and Ketones Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
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1 Chapter 14 Aldehydes, Ketones, and Chiral Molecules 14.1 Aldehydes and Ketones Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
2 Carbonyl Group in Aldehydes A carbonyl group and Ketones In an aldehyde is attached to at least one H atom. In a ketone is attached to two carbon groups. Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
3 Naming Aldehydes An aldehyde Has an IUPAC name in which the -e in the alkane name is changed to -al. Has a common name for the first four aldehydes that use the prefixes form- (1C), acet- (2C), propion- (3C), and butyr- (4C), followed by aldehyde. H C H CH 3 C H CH 3 CH 2 C H methanal ethanal propanal (formaldehyde) (acetaldehyde) (propionaldehyde)
4 Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings Naming Aldehydes
5 Aldehydes in Flavorings Several naturally occurring aldehydes are used as flavorings for foods and fragrances. C H Benzaldehyde (almonds) CH=CH C H Cinnamaldehyde (cinnamon)
6 Naming Ketones Ketones are named In the IUPAC system by replacing the -e in the alkane name with -one. The carbonyl carbon is indicated by a number. With a common name by indicating the alkyl groups attached to the carbonyl group in alphabetical order followed by ketone. CH 3 C CH 3 CH 3 C CH 2 CH 3 propanone 2-butanone (dimethyl ketone) (ethyl methyl ketone)
7 Ketones in Common Use Butter flavoring Nail polish remover, Solvent Propanone, Dimethylketone, Acetone Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
8 Learning Check Classify each as 1) aldehyde or 2) ketone. A. CH 3 CH 2 C CH 3 B. CH 3 C H CH 3 C. CH 3 C CH 2 C H D. CH 3
9 Solution A. 2) ketone B. 1) aldehyde C. 1) aldehyde D. 2) ketone
10 Learning Check Classify each as an aldehyde (1), ketone (2), alcohol (3), or ether (4). A. CH 3 CH 2 C CH 3 B. CH 3 CH 3 CH 3 H C. CH 3 C CH 2 C H D. CH 3 CH CH 3 CH 3
11 Solution Classify each as an aldehyde (1), ketone (2), alcohol (3), or ether (4). A. CH 3 CH 2 C CH 3 B. CH 3 CH 3 (2) ketone (4) ether CH 3 H C. CH 3 C CH 2 C H D. CH 3 CH CH 3 CH 3 (1) aldehyde (3) alcohol
12 Learning Check Name each of the following: 1. CH 3 CH 2 CH 2 CH 2 C H 2. Cl CH 2 CH 2 C H 3. CH 3 CH 2 C CH 3
13 Solution 1. CH 3 CH 2 CH 2 CH 2 C H pentanal 2. Cl CH 2 CH 2 C H 3-chloropropanal 3. CH 3 CH 2 C CH 3 2-butanone; ethyl methyl ketone
14 Learning Check Name the following compounds. A. CH 3 CH 2 CH 2 C CH 3 B. CH 3 C. CH 3 C CH 2 C H CH 3
15 Solution A. 2-pentanone; methyl propyl ketone B. cyclohexanone C, 3,3-dimethylbutanal
16 Chapter 14 Aldehydes, Ketones, and Chiral Molecules 14.2 Physical Properties Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
17 Polar Carbonyl Group The polar carbonyl group Provides dipole-dipole interactions. δ + δ - δ + δ - C= C= Does not have H on the oxygen atom. Cannot form hydrogen bonds.
18 Boiling Points Aldehydes and ketones have Polar carbonyl groups (C=). δ + δ - C= Attractions between polar groups. δ + δ - δ + δ - C= C= Higher boiling points than alkanes and ethers of similar mass. Lower boiling points than alcohols of similar mass.
19 Comparison of Boiling Points 58 Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
20 Learning Check Select the compound in each pair that would have the Higher boiling point. A. CH 3 CH 2 CH 3 or CH 3 CH 2 H B. or C. CH 3 CH 2 H or CH 3 CH 3
21 Solution A. CH 3 CH 2 H B. C. CH 3 CH 2 H
22 Solubility in Water The electronegative atom of the carbonyl group in aldehydes and ketones forms hydrogen bonds with water. Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
23 Learning Check Indicate if each is soluble or insoluble in water. A. CH 3 CH 2 CH 3 B. CH 3 CH 2 H C. CH 3 CH 2 CH 2 C H D. CH 3 C CH 3
24 Solution A. CH 3 CH 2 CH 3 insoluble B. CH 3 CH 2 H soluble C. CH 3 CH 2 CH 2 C H soluble D. CH 3 C CH 3 soluble
25 Chapter 14 Aldehydes, Ketones and Chiral Molecules xidation and Reduction Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
26 xidation Aldehydes are easily oxidized to carboxylic acids. [] CH 3 C H CH 3 C H Acetaldehyde Acetic acid
27 Tollens reagent, which contains Ag +, oxidizes aldehydes, but not ketones. Ag + is reduced to metallic Ag, which appears as a mirror in the test tube. Tollens Test
28 ERRR: stackunderflow FFENDING CMMAND: ~ STACK:
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Unit 9. Organic compounds Index 1.- How to Name Organic Compounds...2 2.- Types of Compounds...3 Exercises...6 Practice exam...9 Page 1 of 11 The IUPAC Naming (nomenclature) System 1.- How to Name Organic
Ketones and Aldehydes
Ketones and Aldehydes Adapted from rganic hemistry, L. G. Wade, Jr. = 1 Violet (Irone) salicylaldehyde (meadowsweet) 3 ( 2 ) 4 (Eucalyptus) 3 ( 2 ) 10 (itrus Fruits) Piperonal (eliotrope) 3 3 Raspberries
Chapter 22 Hydrocarbon Compounds
Chapter 22 Hydrocarbon Compounds 1 ORGANIC COMPOUNDS Organic compounds are carbon compounds and there are over a million. The simplest organic compounds are hydrocarbons and they are composed of hydrogen
ALDEHYDES AND KETONES
11 R R R ALDEYDES AND KETNES APTER SUMMARY 111 Structure of Aldehydes and Ketones Aldehydes and ketones both have a carbonyl group (carbonoxygen double bond); aldehydes have at least one carbon bonded
1. Write the structures of the following compounds. (i) α-methoxypropionaldehyde. (ii) 3-Hydroxybutanal. (iii) 2-Hydroxycyclopentane carbaldehyde
1. Write the structures of the following compounds. (i) α-methoxypropionaldehyde (ii) 3-Hydroxybutanal (iii) 2-Hydroxycyclopentane carbaldehyde (iv) 4-Oxopentanal. (i) (ii) (iii) (iv) 2. Write the structures