Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
5th Edition
ISBN: 9781260170405
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 31, Problem 31.4P
The main fatty acid component of the triacylglycerols in coconut oil is lauric acid,
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The main fatty acid component of the triacylglycerols in coconut oil is lauric acid, CH3(CH2)10COOH. Explain why coconut oil is a liquid at room temperature even though it contains a large fraction of this saturated fatty acid.
4. The ester you drew in Question #1 has a melting point range of 32 - 35 °C. The methyl ester of mono-unsaturated
palmitoleic acid (IUPAC name: hexadec-9-enoic acid) has a considerably lower melting point range: -0.5-+0.5 °C.
a) Explain what it means for a fatty acid to be "mono-unsaturated."
b) Illustrate your explanation by drawing the structure of the methyl ester of octadec-11-enoic acid. (Be sure to draw
the geometric stereoisomer that is commonly found in nature.)
A lipid has the following structure:
CH2-O-CH2-(CH2)16CH3
0
CH-O-C-(CH2)4CH=CHCH2CH=CH(CH2)7CH3
0
||
CH2-O-C-(CH2)4CH-CHCH2CH=CH(CH2)7CH3
Which of the statements are true or false about the structure above
Both this structure and a wax contain one or more carboxyl groups
This lipid and a prostaglandin can both be hydrolyzed in acid to create fatty acids
This lipid and a thromboxane can both be hydrolyzed in base to produce soaps
Both this lipid and a terpene can be very hydrophobic molecules
Based on its structural similarity to other lipids, this lipid most likely functions as a membrane component
Both this structure and a wax contain one or more ester bonds
This lipid and an arachidonic acid both contain glycerol and hydrocarbon chains
Based on its structural similarity to other lipids, this lipid most likely functions as an energy storage molecule
Both this lipid and a terpene can contain isoprene
This lipid and a leukotriene are both polyunsaturated molecules
Both this structure…
Chapter 31 Solutions
Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
Ch. 31 - Problem 31.1
One component of jojoba oil is a wax...Ch. 31 - Problem 31.2
How would you expect the melting...Ch. 31 - Problem 31.3
Draw the products formed when...Ch. 31 - Problem 31.4
The main fatty acid component of the...Ch. 31 - Prob. 31.5PCh. 31 - Problem 31.6
Draw the structure of a lecithin...Ch. 31 - Prob. 31.7PCh. 31 - Problem 31.8
Why are phospholipids, but not...Ch. 31 - Problem 31.9
Explain why regularly ingesting a...Ch. 31 - Problem 31.10
Locate the isoprene units in each...
Ch. 31 - Problem 31.11
Locate the isoprene units in...Ch. 31 - Problem 31.12
Write a stepwise mechanism for the...Ch. 31 - Prob. 31.13PCh. 31 - Prob. 31.14PCh. 31 - Prob. 31.15PCh. 31 - Prob. 31.16PCh. 31 - 31.17 Locate the isoprene units in each...Ch. 31 - Prob. 31.18PCh. 31 - Prob. 31.19PCh. 31 - Prob. 31.20PCh. 31 - Prob. 31.21PCh. 31 - 31.22 What is the structure of an optically...Ch. 31 - Prob. 31.23PCh. 31 - 31.24 Draw the structure of the following...Ch. 31 - Prob. 31.25PCh. 31 - Locate the isoprene units in each compound. a. e....Ch. 31 - 31.27 Classify each terpene and terpenoid in...Ch. 31 - 31.38 Draw the products formed when cholesterol is...Ch. 31 - 31.29 An isoprene unit can be thought of as having...Ch. 31 - 31.30 Draw a stepwise mechanism for the conversion...Ch. 31 - Prob. 31.31PCh. 31 - Prob. 31.32PCh. 31 - Draw three-dimensional structures f or each...Ch. 31 - Prob. 31.34PCh. 31 - Prob. 31.35PCh. 31 - Prob. 31.36PCh. 31 - Prob. 31.37PCh. 31 - 31.38 Draw the products formed when cholesterol is...Ch. 31 - 31.39 Draw a stepwise mechanism for the following...Ch. 31 - 31.40 Draw a stepwise mechanism for the following...Ch. 31 - Prob. 31.41P
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- What is the basis for deciding if a substance is a lipid?arrow_forwardFats belong to the class of organic compounds represented by the general formula, RCOOR', where R and R' represent hydrocarbon groups. What is the name of the functional group present in fats? What functional group is common to all saponifiable lipids?arrow_forwardThe following is a block diagram for a glycerophospholipid where the building blocks are labeled with letters and the linkages between building blocks are labeled with numbers. a. Which building blocks are fatty acid residues? b. Which building blocks are alcohol residues? c. Which linkages are ester linkages? d. Which linkages involve a phosphate residue?arrow_forward
- Give numerical answers to the following questions about the structure of a cholesterol molecule. a. How many six-membered rings arc present? b. How many amide linkages are present? c. How many hydroxyl substituents are present? d. How many total functional groups are present?arrow_forwardIn what way is the structure of glycine different from that of the other 19 common amino acids?arrow_forwardIn a dietary context, what is the difference between good cholesterol and bad cholesterol?arrow_forward
- There are structural differences between saturated fatty acids, cis-unsaturated fatty acids, and trans-unsaturated fatty acids. • Why have some cities banned the use of trans-unsaturated fatty acids at restaurants? Trans-unsaturated fatty acids stack like unsaturated fatty acids and cost more energy to metabolize, making it substantially more dangerous to consume. Trans-unsaturated fatty acids stack like saturated fatty acids and cost more energy to metabolize, making it substantially more dangerous to consume. Trans-unsaturated fatty acids stack like saturated fatty acids and cost less energy to metabolize, making it substantially more dangerous to consume. None of the other answers are correct. O Trans-unsaturated fatty acids stack like unsaturated fatty acids and cost less energy to metabolize, making it substantially more dangerous to consume.arrow_forwardIf an unsaturated fatty acid has 18 carbons, a double bond at position ∆15 would be in ω notation ω - _________? The functional groups which hold fatty acid molecules and glycerol molecules together in triacylglecerol molecules are called: ____________ If a triacylglycerol is heated in aqueous sodium hydroxide (lye) solution glycerol and the sodium salts of fatty acids are produced. This mixture of sodium salts of fatty acids is called in common terminology ________. Name the four parts of phosphatidylcholine. _______, _________, ________ and _________ The molecule found in phospholipids which most resembles glucose is: a) lecithin b) inositol c) choline d) kinetic acid A molecule which contains sphingosine bonded to a fatty acid and a monosaccharide is called ________ A lipid class which contains no fatty acids is called ___________ When phosphatidylcholine (lecithin) is sonicated in water it forms ____________ Membrane fluidity may be regulated by the degree of…arrow_forwardPalmitoleic acid, a fatty acid with various pharmaceutical applications, is mainly obtained from macadamia nuts. The condensed structural formula for a triacylglycerol containing three palmitoleic acid units is provided below. Which of the following statements is NOT true regarding this triacylglycerol? O || CH,−O−C–(CH,)–CH=CH—(CH2)5–CH3 O || CH−O−C−(CH2)–CH=CH–(CH,)5–CH3 O CH,−O−C−(CH,)–CH=CH–(CH,)5–CH, O Its name is glyceryl tripalmitate or tripalmitin. O It is most likely to be liquid at room temperature. O It is an oil (not a fat). O It contains 3 molecules of the same unsaturated fatty acid.arrow_forward
- ew Tab D Ⓡ B Q Question 6 This skeletal structure represents a saturated fatty acid O True O False Question 7 A polyunsaturated fatty acid contains more than one carbon-carbon double bond O carboxyl group O carbonyl group hydroxyprop Olong carbon chain Question 8 Cholesterol belongs to the Osteroid hold group of lipidsarrow_forwardArrange the fatty acids from highest melting point to lowest melting point. - CH3(CH2)10COOH - CH3(CH2)7CH=CH(CH2)7COOH - CH3(CH2)4(CH=CHCH2)4(CH2)2COOH - CH3(CH2)14COOH Select the statements about fatty acid melting points that are true. - A saturated fatty acid with a greater molar mass has a higher melting point than a saturated fatty acid with a lower molar mass. - A saturated fatty acid with a greater molar mass has a lower melting point than a saturated fatty acid with a lower molar mass. - A saturated fatty acid has a higher melting point than an unsaturated fatty acid. - A saturated fatty acid has a lower melting point than an unsaturated fatty acid.arrow_forward1. Abundant trans bonds make partially hydrogenated vegetable oil a very unhealthy food choice. Vegetable oil can also be hydrogenated until it becomes fully saturated with hydrogen atoms. Would the physical properties of the hydrogenated and partially hydrogenated oils differ? If so, how and why would the differences occur? Do you think that full hydrogenation makes vegetable oil more or less healthy to eat, or does it have no effect? 2. Lipoprotein particles are relatively large, spherical clumps of protein and lipid molecules (see Figure 3.18) that circulate in the blood of mammals. They are like suitcases that move cholesterol, fatty acid remnants, triglycerides, and phospholipids from one place to another in the body. Given what you know about the insolubility of lipids in water, which of the four kinds of lipids would you predict to be on the outside of a lipoprotein clump, bathed in the water-based fluid portion of blood? 3. In 1976, a team of chemists in the United Kingdom was…arrow_forward
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