Smith6e Chapter29 TB AnswerKey

Organic Chemistry, 6e (Smith)
Chapter 29 Lipids
1) Provide a definition of the term lipid.

A) A compound with a carbonyl group
B) A compound with an aromatic ring
C) A hydrophobic biomolecule
D) A water-soluble compound
Answer: C
Difficulty: 1 Easy
Section: 29.01
Topic: Lipids
Bloom's: 2. Understand
Chapter: 29
Accessibility: Keyboard Navigation
2) Which of the following compounds is not a lipid?
A) A
B) B
C) C
D) D
Answer: B
Difficulty: 1 Easy
Section: 29.01
Topic: Lipids
Chapter: 29
1
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3) Which of the following compounds is not a hydrolyzable lipid?
A) A
B) B
C) C
D) D
Answer: C
Difficulty: 1 Easy
Section: 29.01
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
4) Evaluate the following statement: The terpene structure shown is a hydrolysable lipid.
A) True, because it contains an alcohol functional group.

B) False, because alcohol and aldehyde moieties are not hydrolysable.
C) True, because there are three polar groups and only 12 total carbon atoms.
D) False, because there is too much steric repulsion from the alcohol and aldehyde moieties.
Answer: B
Difficulty: 1 Easy
Section: 29.07
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
2
5) What happens to the melting point in fatty acids as the unsaturation increases?
A) It increases
B) It decreases.
C) There is no direct correlation between unsaturation and melting point.
D) The melting point stays the same.
Answer: B
Difficulty: 1 Easy
Section: 29.03
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
6) Solid fats are generally from what source?

A) Vegetables
B) Starches
C) Legumes
D) Animals
Answer: D
Difficulty: 1 Easy
Section: 29.03
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
7) Liquid oils usually have a higher percentage of what component compared to solid fats?
A) Oxygen
B) Hydrogen
C) Unsaturation
D) Aromatic rings
Answer: C
Difficulty: 1 Easy
Section: 29.03
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
3
8) How can an unsaturated fatty acid be converted into a saturated fatty acid?
A) Hydrogenation
B) Hydration
C) Ozonolysis
D) Hydrolysis
Answer: A
Difficulty: 1 Easy
Section: 29.03
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
9) What chemical process causes an oil (such as soybean oil) to become rancid?
A) Hydrogenation with hydrogen
B) Hydration with water
C) Oxidation with molecular oxygen
D) Bromination with bromine
Answer: C
Difficulty: 1 Easy
Section: 29.03
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
10) What is the main cellular function of a triacylglycerol?

A) Signal transduction
B) Form cell membranes
C) Nerve cell transferal
D) Energy storage
Answer: D
Difficulty: 1 Easy
Section: 29.03
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
4
11) Which of the following is a phospholipid?
A) A
B) B
C) C
D) D
Answer: B
Difficulty: 1 Easy
Section: 29.04
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
12) What is the purpose of vitamin K?

A) Energy storage
B) Blood clotting
C) Photosynthesis
D) Hydrogenation
Answer: B
Difficulty: 1 Easy
Section: 29.05
Topic: Lipids
Chapter: 29
5
13) Eicosanoids are derived from what compound?
A) Arachidonic acid
B) Cyclohexane
C) Cholesterol
D) Triacylglycerols
Answer: A
Difficulty: 1 Easy
Section: 29.05
Topic: Lipids
Chapter: 29
14) What is the first key enzyme required for the synthesis of prostaglandins from arachidonic
acid?
A) Protein Kinase C
B) Synthase
C) Transferase
D) COX (cyclic oxygenase)
Answer: D
Difficulty: 1 Easy
Section: 29.05
Topic: Lipids
Bloom's: 1. Remember
Chapter: 29
15) What is (are) the basic subunits of terpenes?

A) Cyclohexane
B) Triacylglycerols
C) Isoprene
D) Carbonyls
Answer: C
Difficulty: 1 Easy
Section: 29.07
Topic: Lipids
Bloom's: 1. Remember
Chapter: 29
6
16) How many isoprene units are in the following molecule?
A) 1
B) 2
C) 3
D) 4
Answer: D
Difficulty: 1 Easy
Section: 29.07
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
7
17) How many isoprene units are contained in the following molecule?
A) 5
B) 4
C) 3
D) 2
Answer: B
Difficulty: 2 Medium
Section: 29.07
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
8
18) Which of the following compounds is a steroid?
A) A
B) B
C) C
D) D
Answer: C
Difficulty: 1 Easy
Section: 29.08
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
19) What is (are) the biological precursor(s) for the formation of the steroid skeleton found in
cholesterol?
A) Cyclohexane
B) Squalene
C) Triacylglycerols
D) Arachadonic acid
Answer: B
Difficulty: 1 Easy
Section: 29.08
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
9
20) Which structure represents the lowest energy conformation of a trans-decalin?
A) A
B) B
C) C
D) D
Answer: D
Difficulty: 1 Easy
Section: 29.08
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
21) Which of the following sequences shows a reasonable series of 1,2-rearrangements as might
be found in the biosynthesis of a steroid?
A) A
B) B
C) C
D) D
Answer: A
Section: 29.08
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
10
22) Which of the following is not one of the three main categories of hydrolyzable lipids?
A) Waxes
B) Steroids
C) Triacylglycerols
D) Phospholipids
Answer: B
Difficulty: 1 Easy
Section: 29.08
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
23) Which of the following classes of molecules is not a nonhydrolyzable lipid?

A) Steroids
B) Terpenes
C) Phospholipids
D) Eicosanoids
Answer: C
Difficulty: 1 Easy
Section: 29.08
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
11
24) All except one of the statements below are true about the molecule given. Which statement is
not correct?
A) This molecule is a phospholipid and is generally found in fruits, vegetables, fish, liver, and
dairy products.
B) This molecule is a phospholipid that composes the main fabric of the insoluble barrier that
protects the cell.
C) This molecule contains two fatty acids and has at least one stereogenic center.
D) This molecule is a phospholipid and belongs to the general category of lecithins.
Answer: A
Section: 29.01
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
25) From the statements below, pick out the one that is not correct for fat-soluble vitamins.
A) Fat-soluble vitamins are classified as lipids.
B) Fat-soluble vitamins are a group of biologically active compounds containing 20 carbon
atoms.
C) Fat-soluble vitamins are required in small quantities for normal metabolism.
D) Fat-soluble vitamins are stored in fat cells for use when they are needed.
Answer: B
Difficulty: 1 Easy
Section: 29.05
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
12
26) What is the result of the oxidation of arachidonic acid with O2 by cyclooxygenase?
A) It results in the synthesis of prostaglandins, thromboxanes, and prostacyclins.
B) It results in the synthesis of fat-soluble vitamins from sphingomyelins.
C) It results in the synthesis of phosphoacylglycerols.
D) It is an important step in the synthesis of lipids that form the lipid bilayer.
Answer: A
Section: 29.05
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
27) Triacylglycerol A yields compound B when treated with excess H2, Pd-C. Ozonolysis of A
affords three molecules of compound C and one molecule of compound D. What is the structure
of A?
Choices for Triglycerol A:
A) A
B) B
C) C
D) D
Answer: C
Difficulty: 3 Hard
Section: 29.03
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
13
28) Patchouli alcohol is an example of a terpene. How is this molecule classified?
A) Monoterpene
B) Diterpene
C) Triterpene
D) Sesquiterpene
Answer: D
Section: 29.07
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
14
29) The stereoselective introduction of the C15 OH group on the w side chain of prostaglandins
has presented a challenge for synthetic chemists. Recently, Mulzer and co-workers demonstrated
a new route in which the w side chain is synthesized independently and then attached to the
bicyclic counterpart. What is the appropriate sequence of reagents for the following synthesis?
A) (1) PBr3; (2) Grubbs' catalyst, Reagent X; (3) KOC(CH3)3

B) (1) PCC; (2) Ph3P=CH2; (3) Grubbs' catalyst, Reagent X
C) (1) PBr3; (2) Ph3P=CH2; (3) Grubbs' catalyst, Reagent X
D) (1) TsCl, pyridine; (2) Grubbs' catalyst, Reagent X; (3) KOC(CH3)3
Answer: B
Section: 29.04
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
15
30) Norethindrone is a synthetic steroid that is better than progesterone in suppressing ovulation.
What reagents (1-3) are required to convert norethindrone to the derivatives shown below?
A) (1) H2, Pd-C; (2) (CH3)2CHCH2NH2, NaBH3CN; (3) a. O3, b. Zn, DMS
B) (1) H2, Pd-C; (2) (CH3)2CHCH2NH2, mild acid; (3) a. O3, b. Zn, DMS
C) (1) a. LiAlH4, b. H2O; (2) (CH3)2CHCH2NH2, NaBH3CN; (3) a. OsO4, b. NaHSO3
D) (1) a. LiAlH4, b. H2O; (2) (CH3)2CHCH2NH2, mild acid; (3) a. OsO4, b. NaHSO3
Answer: A
Section: 29.08
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
16
31) Sphingomyelins are a major component of the myelin sheath. Damage to the myelin sheath
results in such diseases as multiple sclerosis. Which compound below corresponds to a
sphingomyelin?
A) A
B) B
C) C
D) D
Answer: C
Section: 29.04
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
32) Which of the following are complex lipids?

A) Steroids
B) Terpenes
C) Waxes
D) Protaglandins
Answer: C
Difficulty: 1 Easy
Section: 29.02
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
17
33) Which of the following are simple lipids?
A) Steroids
B) Terpenes
C) Waxes
D) Prostaglandins
Answer: A
Difficulty: 1 Easy
Section: 29.07
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
34) Which of the following correctly describes waxes?

A) Long chain alcohols
B) Long chain esters
C) Long chain ethers
D) Long chain fatty acids
Answer: B
Difficulty: 1 Easy
Section: 29.02
Topic: Lipids
Chapter: 29
35) What is the correct classification of the following compound?

CH3(CH2)15COOH
A) Saturated triglyceride
B) Simple lipid
C) Wax
D) Saturated fatty acid
Answer: D
Difficulty: 1 Easy
Section: 29.03
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
18
36) Which of the following fatty acids has the highest melting point?
A) Palmitic acid
B) Arachidic acid
C) Stearic acid
D) Lauric acid
Answer: B
Difficulty: 1 Easy
Section: 29.03
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
37) Which of the following fatty acids has the lowest melting point?
A) Palmitic acid
B) Arachidic acid
C) Stearic acid
D) Lauric acid
Answer: D
Difficulty: 1 Easy
Section: 29.03
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
38) Which of the following fatty acids has the highest melting point?
A) Linoleic acid
B) Oleic acid
C) Arachidonic acid
D) Palmitoleic acid
Answer: B
Difficulty: 1 Easy
Section: 29.03
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
19
39) Which of the following fatty acids has the lowest melting point?
A) Linoleic acid
B) Oleic acid
C) Arachidonic acid
D) Palmitoleic acid
Answer: C
Difficulty: 1 Easy
Section: 29.03
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
40) Which of the following fatty acids is not present in natural fats and oils?
A) Hexadecanoic acid
B) Heptadecanoic acid
C) Octadecanoic acid
D) None of the choices
Answer: B
Difficulty: 1 Easy
Section: 29.03
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
41) What is the name of the reaction of triglycerides with a base?

A) Esterification
B) Transesterification
C) Ozonolysis
D) Saponification
Answer: D
Difficulty: 1 Easy
Section: 29.03
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
20
42) What is the structure of a cortisone derivative that has a C=C between C6 and C7, methyl
group at C8 and chlorine at C12? The configuration of C8 is S and the configuration at C12 is R.
A) I
B) II
C) III
D) IV
Answer: C
Difficulty: 3 Hard
Section: 29.08
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
43) How many isoprene units can be found in the following compound?
A) 1
B) 4
C) 8
D) 9
Answer: B
Section: 29.07
Topic: Lipids
Bloom's: 3. Apply
Chapter: 29
21
44) Which state about waxes is not true?
A) Waxes are esters
B) Waxes are formed from a high molecular weight alcohol and a fatty acid
C) Waxes are water soluble
D) Waxes are the simplest hydrolysable lipid
Answer: C
Difficulty: 1 Easy
Section: 29.02
Topic: Lipids
Chapter: 29
45) Which of the following is a fat soluble vitamin?

A) Vitamin A
B) Vitamin D3
C) Vitamin K
D) All of these choices are correct
Answer: D
Difficulty: 1 Easy
Section: 29.05
Topic: Lipids
Chapter: 29
22

Smith6e Chapter29 TB AnswerKey

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Smith6e Chapter29 TB AnswerKey

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Organic Chemistry, 6e (Smith)

1) Provide a definition of the term lipid.

2) Which of the following compounds is not a lipid?

A) True, because it contains an alcohol functional group.

6) Solid fats are generally from what source?

10) What is the main cellular function of a triacylglycerol?

12) What is the purpose of vitamin K?

15) What is (are) the basic subunits of terpenes?

23) Which of the following classes of molecules is not a nonhydrolyzable lipid?

Choices for Triglycerol A:

A) (1) PBr3; (2) Grubbs' catalyst, Reagent X; (3) KOC(CH3)3

32) Which of the following are complex lipids?

34) Which of the following correctly describes waxes?

35) What is the correct classification of the following compound?

41) What is the name of the reaction of triglycerides with a base?

45) Which of the following is a fat soluble vitamin?

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