Organic Chemistry 6th Edition solutions

Organic Chemistry 6
How many constitutional isomers are possible for a triglyceride containing one molecule each of palmitic acid, oleic acid, and stearic acid?

Organic Chemistry 6
Which of these constitutional isomers are chiral?

Organic Chemistry 6
Explain why the melting points of unsaturated fatty acids are lower than those of saturated fatty acids.

Organic Chemistry 6
Which would you expect to have the higher melting point, glyceryl trioleate or glyceryl trilinoleate?

Organic Chemistry 6
Draw a structural formula for methyl linoleate. Be certain to show the correct confi guration of groups about each carbon-carbon double bond

Organic Chemistry 6
Explain why coconut oil is a liquid triglyceride, even though most of its fatty acid components are saturated.

Organic Chemistry 6
It is common now to see contains no tropical oils on cooking oil labels, meaning that the oil contains no palm or coconut oil. What is the difference between the composition of tropical oils and that of vegetable oils, such as corn oil, soybean oil, and peanut oil?

Organic Chemistry 6
What is meant by the term hardening as applied to vegetable oils?

Organic Chemistry 6
How many moles of H2 are used in the catalytic hydrogenation of one mole of a triglyceride derived from glycerol and equal portions of stearic acid, linoleic acid, and arachidonic acid?

Organic Chemistry 6
Characterize the structural features necessary to make a good synthetic detergent.

Organic Chemistry 6
Following are structural formulas for a cationic detergent and a neutral detergent. Account for the detergent properties of each. CH3(CH2)6CH2NCH3 Cl 1 HOCH2CCH2OC(CH2)14CH3 HOCH2 HOCH2 CH3 CH2C6H5 Benzyldimethyloctylammonium chloride (a cationic detergent) Pentaerythrityl palmitate (a neutral deterg

Organic Chemistry 6
Identify some of the detergents used in shampoos and dish-washing liquids. Are they primarily anionic, neutral, or cationic detergents?

Organic Chemistry 6
Show how to convert palmitic acid (hexadecanoic acid) into the following. (a) Ethyl palmitate (b) Palmitoyl chloride (c) 1-Hexadecanol (cetyl alcohol) (d) 1-Hexadecanamine (e) N,N- Dimethylhexadecanamide

Organic Chemistry 6
Palmitic acid (hexadecanoic acid) is the source of the hexadecyl (cetyl) group in the following compounds. Each is a mild surface-acting germicide and fungicide and is used as a topical antiseptic and disinfectant. They are examples of quaternary ammonium detergents, commonly called quats. CH2(CH2)14

Organic Chemistry 6
Lipases are enzymes that catalyze the hydrolysis of esters, especially esters of glycerol. Because enzymes are chiral catalysts, they catalyze the hydrolysis of only one enantiomer of a racemic mixture. For example, porcine pancreatic lipase catalyzes the hydrolysis of only one enantiomer of the foll

Organic Chemistry 6
Examine the structure of PGF2a. Identify all chiral centers and all double bonds about which cis,trans isomerism is possible, and state the number of stereoisomers possible for a molecule of this structure

Organic Chemistry 6
Following is the structure of unoprostone, a compound patterned after the natural prostaglandins (Section 26.3). Rescula, the isopropyl ester of unoprostone, is an antiglaucoma drug used to treat ocular hypertension. Compare the structural formula of this synthetic prostaglandin with that of PGF2a. U

Organic Chemistry 6
Doxaprost, an orally active bronchodilator patterned after the natural prostaglandins (Section 26.3), is synthesized in the following series of reactions starting with ethyl 2-oxocyclopentanecarboxylate. Except for the Nef reaction in Step 8, we have seen examples of all other types of reactions invo

Organic Chemistry 6
Draw the structural formula for the product formed by treatment of cholesterol with H2/Pd; with Br2.

Organic Chemistry 6
Draw the structural formula for the product formed by treatment of cholesterol with H2/Pd; with Br2.

Organic Chemistry 6
Examine the structural formulas of testosterone (a male sex hormone) and progesterone (a female sex hormone). What are the similarities in structure between the two? What are the differences?

Organic Chemistry 6
Examine the model of cholic acid (Problem 2.65) and account for the ability of this and other bile salts to emulsify fats and oils and thus aid in their digestion.

Organic Chemistry 6
Following is a structural formula for cortisol (hydrocortisone). Draw a stereorepresentation of this molecule showing the conformations of the fi ve- and sixmembered rings. Cortisol (Hydrocortisone) H3C O H H H HO CH3 C O OH CH2OH

Organic Chemistry 6
Much of our understanding of conformational analysis has arisen from studies on the reactions of rigid steroid nuclei. For example, the concept of trans-diaxial ring opening of epoxycyclohexanes was proposed to explain the stereoselective reactions seen with steroidal epoxides. Predict the product wh

Organic Chemistry 6
Draw the structural formula of a lecithin containing one molecule each of palmitic acid and linoleic acid.

Organic Chemistry 6
Identify the hydrophobic and hydrophilic region(s) of a phospholipid

Organic Chemistry 6
The hydrophobic effect is one of the most important noncovalent forces directing the self-assembly of biomolecules in aqueous solution. The hydrophobic effect arises from tendencies of biomolecules (1) to arrange polar groups so that they interact with the aqueous environment by hydrogen bonding and

Organic Chemistry 6
How does the presence of unsaturated fatty acids contribute to the fl uidity of biological membranes?

Organic Chemistry 6
Lecithins can act as emulsifying agents. The lecithin of egg yolk, for example, is used to make mayonnaise. Identify the hydrophobic part(s) and the hydrophilic part(s) of a lecithin. Which parts interact with the oils used in making mayonnaise? Which parts interact with the water?

Organic Chemistry 6
Examine the structural formula of vitamin A, and state the number of cis,trans isomers possible for this molecule.

Organic Chemistry 6
The form of vitamin A present in many food supplements is vitamin A palmitate. Draw the structural formula of this molecule.

Organic Chemistry 6
Examine the structural formulas of vitamin A, 1,25-dihydroxy-D3, vitamin E, and vitamin K1 (Section 26.6). Do you expect them to be more soluble in water or in dichloromethane? Do you expect them to be soluble in blood plasma?