Organic Chemistry 2nd Edition solutions

Organic Chemistry 2
Identify each of the following compounds as a wax, triglyceride, phospholipid, steroid, prostaglandin, or terpene: (a) Stanozolol (b) Lycopene (c) Tristearin (d) Distearoyl lecithin (e) PGF2 (f) Pentadecyl octadecanoate

Organic Chemistry 2
Predict the product(s) formed when tripalmitolein is treated with each of the following reagents: (a) Excess H2, Ni (b) Excess NaOH, H2O

Organic Chemistry 2
Draw two different cephalins that contain one lauric acid residue and one myristic acid residue. Are both of these compounds chiral?

Organic Chemistry 2
Draw an optically active triglyceride that contains one palmitic acid residue and two myristic acid residues. Will this compound react with molecular hydrogen in the presence of a catalyst?

Organic Chemistry 2
Which of the following compounds are lipids? (a) l-Threonine (b) 1-Octanol (c) Lycopene (d) Trimyristin (e) Palmitic acid (f) d-Glucose (g) Testosterone (h) d-Mannose

Organic Chemistry 2
Draw the structure of trans-oleic acid.

Organic Chemistry 2
Tristearin is less susceptible to becoming rancid than triolein. Explain.

Organic Chemistry 2
Arrange the following compounds in order of increasing water solubility: (a) A triglyceride constructed from one equivalent of glycerol and three equivalents of myristic acid (b) A diglyceride constructed from one equivalent of glycerol and two equivalents of myristic acid (c) A monoglyceride constru

Organic Chemistry 2
Identify whether hexane or water would be more appropriate for extracting terpenes from plant tissues. Explain your choice.

Organic Chemistry 2
Identify each of the following fatty acids as saturated or unsaturated: (a) Palmitic acid (b) Myristic acid (c) Oleic acid (d) Lauric acid (e) Linoleic acid (f) Arachidonic acid

Organic Chemistry 2
Which of the fatty acids in the previous problem has four carbon-carbon double bonds?

Organic Chemistry 2
Which of the following statements applies to triolein? (a) It is a solid at room temperature. (b) It is unreactive toward molecular hydrogen in the presence of Ni. (c) It undergoes hydrolysis to produce unsaturated fatty acids. (d) It is a complex lipid. (e) It is a wax. (f) It has a phosphate group.

Organic Chemistry 2
Identify which of the following statements applies to tristearin: (a) It is a solid at room temperature. (b) It is unreactive toward molecular hydrogen in the presence of Ni. (c) It undergoes hydrolysis to produce unsaturated fatty acids. (d) It is a complex lipid. (e) It is a wax. (f) It has a phosp

Organic Chemistry 2
One of the compounds present in carnauba wax was isolated, purified, and then treated with aqueous sodium hydroxide to yield an alcohol with 30 carbon atoms and a carboxylate ion with 20 carbon atoms. Draw the likely structure of the compound.

Organic Chemistry 2
Draw the structures of trimyristin and tripalmitin and determine which is expected to have the lower melting point. Explain your choice.

Organic Chemistry 2
Draw a mechanism for the transesterification of trimyristin using excess isopropanol in the presence of an acid catalyst.

Organic Chemistry 2
Draw a mechanism for the base-catalyzed transesterification of trimyristin using ethanol in the presence of sodium hydroxide.

Organic Chemistry 2
Draw the structure of an optically inactive triglyceride that contains two oleic acid residues and one palmitic acid residue.

Organic Chemistry 2
Draw the structure of an optically active triglyceride that contains two oleic acid residues and one palmitic acid residue.

Organic Chemistry 2
Draw the enantiomer of cholesterol.

Organic Chemistry 2
Circle the isoprene units in each of the following compounds: (a) Bisabolene (b) Flexibilene (c) Humulene Vitamin A OH (d) Geraniol OH (e) (f) Sabinene

Organic Chemistry 2
Sphingomyelins are lipids with the following general structure: Sphingomyelins OH N H O R Fatty acid residue O P O O O N ! @ (a) Identify the polar head and all hydrophobic tails in sphingomyelins. (b) Do sphingomyelins have the appropriate structural features and three-dimensional geometry necessary

Organic Chemistry 2
Treatment of cholesterol with MCPBA could potentially produce two diastereomeric epoxides. (a) Draw both diastereomeric epoxides. (b) Only one of these epoxides is formed. Predict which one and explain why the other is not formed.

Organic Chemistry 2
Identify the products expected when estradiol is treated with each of the following reagents: (a) Excess Br2 (b) PCC (c) A strong base followed by excess ethyl iodide (d) Excess acetyl chloride in the presence of pyridine

Organic Chemistry 2
Olestra is a noncaloric oil substitute that is produced by esterifying sucrose with eight equivalents of fatty acids obtained from the hydrolysis of vegetable oils. The eight fatty acid residues give Olestra the consistency and flavor of cooking oil, but the steric bulk of the compound prevents diges

Organic Chemistry 2
Identify the reagents you would use to convert oleic acid into each of the following compounds: (a) Stearic acid (b) Ethyl stearate (c) 1-Octadecanol (d) Nonanedioic acid (e) 2-Bromostearic acid

Organic Chemistry 2
Limonene is an optically active compound isolated from the peels of lemons and oranges. (a) Is limonene a monoterpene or a diterpene? (b) Treatment of limonene with excess HBr yields a compound with molecular formula C10H18Br2. Identify the structure of this compound and determine whether it is chira

Organic Chemistry 2
Starting with the following compound and using any other reagents of your choice, outline a synthesis for trimyristin: O O O H

Organic Chemistry 2
The following compound was isolated from nerve cells: O O O O O (a) Describe how this compound differs in structure from fats and oils. (b) Three products are obtained when this compound is hydrolyzed with aqueous sodium hydroxide. Draw the structures of all three products. (c) Four products are obta