Exam #4 Review Sheet
CHEM 2124
Spring, 2014
Exam is Friday May 2nd
I. Carbonyl Compounds – Chapters 16 and 17
o Distinguish aldehydes, ketones, and carboxylic acids
o Bond angles, polarity, and solubility of carbonyl compounds
o Nomenclature rules for aldehydes, ketones, carboxylic acids
o Common name structures, KNOW – formaldehyde, acetaldehyde, benzaldehyde, acetone,
acetic acid, and benzoic acid structures
o Physical properties: BP of aldehydes and ketones higher than hydrocarbons but lower than
alcohols, BP of carboxylic acids are higher than alcohols – WHY?
o Formation of acetals and hemiacetals
 Be able to draw structures of both hemiacetals and acetals formed with addition of alcohol
to a carbonyl group
 Be able to draw cyclic hemiacetal structures when the hydroxyl and carbonyl groups are in
the SAME molecule (Example: 5-hydroxypentanal)
Recommended Textbook Problems (All answers are in the back of the book): 16.31, 16.33, 16.35, 16.37,
16.41, 16.45, 16.47, 16.49, 16.51, 16.71, 16.73 (b and d only), 16.75, 16.77, 16.79, Chapter 17 – a pdf
file of this chapter is on the course website – recommended problems and answers are circled in
purple pen.
II. Carbohydrates – Chapter 20
o All carbohydrates have multiple hydroxyl groups (polyhydroxylated-alcohol) and a carbonyl
group (either aldehyde or ketone)
o Definitions of the following: monosaccharide, disaccharide, polysaccharide, aldose, ketose,
Penultimate carbon, anomeric carbon, anomers, glycosidic bond
o Nomenclature of carbohydrates
 Suffix is –ose
 Classified according to aldehyde or ketone AND # of carbons present ex. aldopentose
 DO NOT HAVE TO MEMORIZE STRUCTURES OF SPECIFIC SUGARS ex. D-Glucose
o Fischer Projection
 How do you draw aldoses and ketoses?
 How do we distinguish a D sugar from an L sugar?
o Cyclic structures
 Aldehydes and ketones react with alcohols to form hemiacetals
 Monosaccharides have both hydroxyl and carbonyl groups in the same molecule so they
exist almost exclusively as cyclic hemiacetals
o Haworth Projections
 New stereocenter created in forming the cyclic structure is called anomeric carbon
 YOU MUST BE ABLE TO CONVERT A FISCHER PROJECTION TO THE CORRECT
HAWORTH PROJECTION – FOLLOW RULES DISCUSSED IN CLASS!!
 Be familiar with the different parts of a cyclic carbohydrate – for example, identify the
anomeric carbon, number the carbons, alpha or beta anomer, etc.
o Disaccharides and Polysaccharides – examples of each
 What is a glycosidic bond? – where does it form? (between an anomeric carbon of one
monosaccharide unit and and –OH group of a second monosaccharide unit)
 Be able to tell me what kind of glycosidic bond is present given the structure of a molecule
(for example: β-14-glycosidic bond)
 DO NOT MEMORIZE STRUCTURES
 What are the common disaccharides and polysaccharides and where are they found?

What are the polysaccharides that comprise starch?
Recommended Textbook Problems (All answers are in the back of the book): 20.27, 20.29, 20.31, 20.33,
20.37, 20.39, 20.41, 20.45, 20.47, 20.49, 20.63, 20.65, 20.67 (a through d only), 20.69, 20.73
III. Lipids – Chapter 19
o What are lipids?
o What are the structural commonalities of all lipids?
o Definitions: Hydrolyzable lipids, nonhydrolyzable lipids, fatty acids, saturated fatty acids,
unsaturated fatty acids, triglycerides (triacylglycerols), simple triglycerides, mixed triglycerides,
trans fats, saponification
o KNOW THE STRUCTURE OF GLYCEROL
o Hydrophilic and hydrophobic portions of fatty acids – given a fatty acid, find each part
o How is melting point of fatty acids related to the fatty acid structure?
o Reaction for the formation of a triacylglycerol given fatty acid structures
o What is a soap? Metal salts of fatty acids – formed through base hydrolysis of a triglyceride
o Given the structure of a triglyceride and a metallic base, what is the structure of the soap formed?
What is the other product that is formed?
Recommended Textbook Problems (All answers are in the back of the book): 19.35, 19.37, 19.39 (a
through d only), 19.55
IV. Amines – Chapter 18
o What is the functional group in an amine?
o What is the structural difference between primary (1°), secondary (2°), and tertiary (3°) amines?
o Shapes, bond angles, and physical properties of amines
 Polarity, hydrogen bonding, boiling/melting points (Ether<Amine<Alcohol), (Tertiary<
Secondary<Primary)
o Amine nomenclature:
 Primary amines – can use systematic (IUPAC) or common names
 Secondary and tertiary amines – Rules for compounds with identical vs. non-identical
substituents
 Recall the structure of aniline
 What is the structure of an amino group?
o Amines as bases – what happens when an amine is reacted with an acid? Why is this important in
the world of medicine? How is the polarity of the molecule impacted in this reaction?
o What is a quaternary ammonium salt?
Recommended Textbook Problems (All answers are in the back of the book): 18.31, 18.37, 18.39, 18.41,
18.43, 18.47, 18.49, 18.53, 18.55, 18.57