1. Chapter 16 An Introduction to Carbonyl and Carboxyl Compounds CHEM 2124 – General Chemistry II Alfred State College Professor Bensley

2. Learning Objectives  Identify the characteristics of aldehydes, ketones, and carboxylic acids.  Name aldehydes, ketones, and carboxylic acids.  Give examples of usefule aldehydes, ketones, and carboxylic acids.  Identify and prepare hemiacetals and acetals.

3. Carbonyl and Carboxyl Compounds I. Structure, Bonding, and Physical Properties

4. Carbonyl and Carboxyl Compounds C. Bond Angles, Polarity D. Boiling Points/Melting Points/Hydrogen Bonding Increasing boiling point CH 3 CH 2 CH 2 CH 2 CH 3 pentane bp 36 o C CH 3 CH 2 CH 2 CHO butanal bp 76 o C

5. Carbonyl and Carboxyl Compounds Increasing boiling point CH 3 CH 2 COCH 3 2-butanone bp 80 o C CH 3 CH 2 CH 2 CH 2 OH 1-butanol bp 118 o C Increasing boiling point E. Solubility

6. A. Aldehydes CH 3 CHCH CH 3 C O H butane  butanal 123 Answer: 2,3-dimethylbutanal Carbonyl and Carboxyl Compounds II. Nomenclature formaldehyde acetaldehydebenzaldehyde

7. B. Ketones CHCH 2 CH 3 CH 3 C O pentane  pentanone 23 Answer: 3-methyl-2-pentanone 1 Carbonyl and Carboxyl Compounds acetoneacetophenonebenzophenone

8. C. Carboxylic Acids CH 3 CHCHCH 2 CH 2 CH 3 C O hexane  hexanoic acid 145 Answer: 4,5-dimethylhexanoic acid OH Carbonyl and Carboxyl Compounds formic acidacetic acidbenzoic acid

9. Formaldehyde (CH 2 ═O) is the simplest aldehyde: It is sold as formalin, a 37% aqueous solution used to preserve biological specimens. Carbonyl and Carboxyl Compounds III.Interesting Carbonyl Compounds

10. Acetone [(CH 3 ) 2 C═O] is the simplest ketone Carbonyl and Carboxyl Compounds Formic acid (HCO 2 H) Acetic acid (CH 3 CO 2 H) Hexanoic acid [(CH 3 (CH 2 ) 4 COOH)]

11. Aldehydes undergo addition reactions with alcohols to form hemiacetals and acetals (in the presence of H 2 SO 4 ). Carbonyl and Carboxyl Compounds IV.Acetal and Hemiacetal Formation

12. Cyclic hemiacetals containing 5 or 6 membered rings are stable compounds. Carbonyl and Carboxyl Compounds

13. Cyclic hemiacetals are converted to cyclic acetals by reaction with another alcohol.