Aldehydes and Ketones Chapter 14 Structure Aldehydes and ketones contain a carbonyl group which consists of a carbon double-bonded to an oxygen. O C In aldehydes, the carbonyl group is at the end. In ketones, the carbonyl group is located within O O the chain. C C H R Aldehyde R R Ketone Properties Polar compounds Boiling points higher than ethers and hydrocarbons but less than alcohols Alkanes < Ethers < Aldehydes and Ketones < Alcohols Aldehydes and ketones with less than five carbons are soluble in water. Properties Practice Problem 1 Which member in each pair would have a higher boiling point? O A. O CH3COH CH3CCH3 O B. CH3CH2CH2CH3 CH3CH2CH Properties Practice Problem 1 Answer Which member in each pair would have a higher boiling point? O A. O CH3COH CH3CCH3 O B. CH3CH2CH2CH3 CH3CH2CH Properties Practice Problem 2 Which member in each of the following pairs will be more water soluble? O O A. CH3CH2CH2CCH2CH2CH3 B. CH3CH2CH O CH3CH2CH2CH3 CH3CH2CH Properties Practice Problem 2 Which member in each of the following pairs will be more water soluble? O O A. CH3CH2CH2CCH2CH2CH3 B. CH3CH2CH O CH3CH2CH2CH3 CH3CH2CH IUPAC Nomenclature of Aldehydes Determine the parent chain which is the longest continuous chain containing the carbonyl group. Replace the final –e with –al. Number the chain beginning with the carbonyl carbon. Number and name all substituents as usual. NAMING ALDEHYDES THE IUPAC WAY a) b) See page 399 question 14.3: CH3 O CH3CHCHCH2-C-H CH3 O CH3CH-C-H Cl Naming Aldehydes the IUPAC way c) O CH3CH2CH2CH-C-H CH2CH3 d) O CH3CHCH2-C-H OH Common Names for Aldehydes Formaldehyde AKA methanal Acetaldehyde AKA ethanal Others 398 can be found in Table 14.1 on pg. IUPAC Nomenclature for Ketones Very similar to naming aldehydes The –e ending is replaced with –one. The location of the carbonyl carbon is indicated with a number. The longest chain is numbered to give the carbonyl carbon the lowest possible number. Naming Ketones the IUPAC way See page 401 question 14.5 O O a) CH3CH-C-CH3 b) CH3CH-C-CH3 I CH3 O O c) CH3CH-C-CH2CH3 d) CH3CHCH2-C-CH3 F CH2CH2CH2CH 3 Common Nomenclature for Ketones Propanone is also known as acetone. Name the alkyl groups that are bonded to the carbonyl carbon. Use these as prefixes followed by the word ketone. Arrange the alkyl groups alphabetically. KETONES- COMMON NAMES O a) CH3CH-C-CH3 O c) CH3CH-C-CH2CH3 O b) CH3CH-C-CH3 CH3 d) O CHCH2-C-CH3 CH2CH2CH2CH Homework Pg. 418: # 14.25, 26, 27, 31, 33, 35, & 36