Deck 27: Biomolecules: Lipids

Question 1

Exhibit 27-2
Refer to the structures of the terpenes below to answer the following question(s).
​
Show the positions of the isoprene units in each of the indicated terpenes.
​
abietic acid

Answer 1

Question 2

Exhibit 27-3
Indicate by asterisks the stereogenic centers present in each of the indicated terpenes.
grandisol

Answer 2

Question 3

Exhibit 27-3
Indicate by asterisks the stereogenic centers present in each of the indicated terpenes.
abietic acid

Answer 3

Question 4

Exhibit 27-1
MATCH each of the following terms to a structure from the list below.There is only one correct structure for each term,and structures may be used more than once.Place the letter of the structure in the blank to the left of the corresponding term.

_____ a triglyceride

A)

B)
C)

D)

E)

F)

G)Malonyl ACP
H)

I)

J)

Question 5

Exhibit 27-1
MATCH each of the following terms to a structure from the list below.There is only one correct structure for each term,and structures may be used more than once.Place the letter of the structure in the blank to the left of the corresponding term.

_____ a sphingomyelin

A)

B)
C)

D)

E)

F)

G)Malonyl ACP
H)

I)

J)

Question 6

Exhibit 27-1
MATCH each of the following terms to a structure from the list below.There is only one correct structure for each term,and structures may be used more than once.Place the letter of the structure in the blank to the left of the corresponding term.

_____ starting material for fatty acid biosynthesis.

A)

B)
C)

D)

E)

F)

G) Malonyl ACP
H)

I)

J)

Question 7

Exhibit 27-1
MATCH each of the following terms to a structure from the list below.There is only one correct structure for each term,and structures may be used more than once.Place the letter of the structure in the blank to the left of the corresponding term.

_____ a phosphoglyceride

A)

B)
C)

D)

E)

F)

G)Malonyl ACP
H)

I)

J)

Question 8

Exhibit 27-1
MATCH each of the following terms to a structure from the list below.There is only one correct structure for each term,and structures may be used more than once.Place the letter of the structure in the blank to the left of the corresponding term.

_____ a sesquiterpene

A)

B)
C)

D)

E)

F)

G)Malonyl ACP
H)

I)

J)

Question 9

Exhibit 27-2
Refer to the structures of the terpenes below to answer the following question(s).
​
Show the positions of the isoprene units in each of the indicated terpenes.
​
α-santonin

Question 10

Exhibit 27-2
Refer to the structures of the terpenes below to answer the following question(s).
​
Show the positions of the isoprene units in each of the indicated terpenes.
​
linalool

Question 11

Bolecic acid,C₁₈H₂₆O₂,yields stearic acid,CH₃(CH₂)₁₆COOH,on catalytic hydrogenation.Ozonolysis of bolecic acid yields the following products:
​
CH₂O HOOC−COOH,HOOC(CH₂)₇COOH,and OHC(CH₂)₄COOH
​
Propose a structure for bolecic acid.

Question 12

Exhibit 27-1
MATCH each of the following terms to a structure from the list below.There is only one correct structure for each term,and structures may be used more than once.Place the letter of the structure in the blank to the left of the corresponding term.

_____ monoterpene precursor

A)

B)
C)

D)

E)

F)

G)Malonyl ACP
H)

I)

J)

Question 13

Exhibit 27-1
MATCH each of the following terms to a structure from the list below.There is only one correct structure for each term,and structures may be used more than once.Place the letter of the structure in the blank to the left of the corresponding term.

_____ a prostaglandin

A)

B)
C)

D)

E)

F)

G)Malonyl ACP
H)

I)

J)

Question 14

Exhibit 27-3
Indicate by asterisks the stereogenic centers present in each of the indicated terpenes.
α-santonin

Question 15

Exhibit 27-2
Refer to the structures of the terpenes below to answer the following question(s).
​
Show the positions of the isoprene units in each of the indicated terpenes.
​
grandisol

Question 16

Exhibit 27-1
MATCH each of the following terms to a structure from the list below.There is only one correct structure for each term,and structures may be used more than once.Place the letter of the structure in the blank to the left of the corresponding term.

_____ a glycerophospholipid

A)

B)
C)

D)

E)

F)

G)Malonyl ACP
H)

I)

J)

Question 17

Exhibit 27-1
MATCH each of the following terms to a structure from the list below.There is only one correct structure for each term,and structures may be used more than once.Place the letter of the structure in the blank to the left of the corresponding term.

_____ a steroid

A)

B)
C)

D)

E)

F)

G)Malonyl ACP
H)

I)

J)

Question 18

Exhibit 27-1
MATCH each of the following terms to a structure from the list below.There is only one correct structure for each term,and structures may be used more than once.Place the letter of the structure in the blank to the left of the corresponding term.

_____ a soap

A)

B)
C)

D)

E)

F)

G)Malonyl ACP
H)

I)

J)

Question 19

Exhibit 27-2
Refer to the structures of the terpenes below to answer the following question(s).
​
Show the positions of the isoprene units in each of the indicated terpenes.
​
lineatin

Question 20

Exhibit 27-2
Refer to the structures of the terpenes below to answer the following question(s).
​
Show the positions of the isoprene units in each of the indicated terpenes.
​
ocimene

Question 21

Exhibit 27-3
Indicate by asterisks the stereogenic centers present in each of the indicated terpenes.
lineatin

Question 22

Plant extracts,called essential oils,are largely a mixture of these lipids.

A)sphingolipids
B)prostaglandins
C)phosphoglycerides
D)terpenoids

Question 23

Male sex hormones like testosterone are called:

A)androgens
B)estrogens
C)progestins
D)glucocorticoids

Question 24

The major lipid components of cell membranes are:

A)sphingolipids
B)prostaglandins
C)phosphoglycerides
D)terpenoids

Question 25

When soaps disperse in water,the long hydrocarbon tails cluster together in a hydrophobic ball,while the ionic heads on the surface of the cluster stick out into the water.These spherical clusters are called:

A)fatty acid esters
B)triacylglycerols
C)lipid bilayers
D)micelles

Question 26

Cell membranes,which form an effective barrier to the passage of ions and other components into and out of the cell,are:

A)fatty acid esters
B)tricacylglycerols
C)lipid bilayers
D)micelles

Question 27

Exhibit 27-4
Draw the structures of the major organic product(s) you would expect to obtain from reaction of androsterone with each of the following reagents.
NaH,then CH₃I

Question 28

Exhibit 27-4
Draw the structures of the major organic product(s) you would expect to obtain from reaction of androsterone with each of the following reagents.
PCC

Question 29

In humans,most steroids function as:

A)enzymes
B)hormones
C)nucleic acids
D)proteins

Question 30

Explain why soaps produce a scum when used in hard water (water containing divalent ions such as magnesium and calcium).

Question 31

Draw and name the product of the complete reaction of the following with glycerol.Atoms other than hydrogen and oxygen are labeled.

Question 32

Abietic acid is an example of:

A)a monoterpene
B)a sesquiterpene
C)a diterpene
D)a sesterterpene

Question 33

Exhibit 27-4
Draw the structures of the major organic product(s) you would expect to obtain from reaction of androsterone with each of the following reagents.
NaBH₄,ethanol

Question 34

A group of C₂₀ lipids that contain a five-membered ring with two long side chains.

A)sphingolipids
B)prostaglandins
C)phosphoglycerides
D)terpenoids

Question 35

Exhibit 27-3
Indicate by asterisks the stereogenic centers present in each of the indicated terpenes.
linalool

Question 36

Chemically,these are triacylglycerols,triesters of glycerol with three long-chain carboxylic acids.

A)waxes
B)fats and oils
C)fatty acids
D)soaps

Question 37

Suggest a mechanism by which caryophyllene is transformed into humulene by treatment with acid.

Question 38

Draw the most stable chair conformation of terpin hydrate.

Question 39

Exhibit 27-4
Draw the structures of the major organic product(s) you would expect to obtain from reaction of androsterone with each of the following reagents.
CH₃COCl,pyridine

Question 40

Mixtures of esters of long-chain carboxylic acids with long-chain alcohols are called:

A)waxes
B)fats and oils
C)fatty acids
D)soaps

Question 41

Using a condensed formula,draw the product of the complete reaction of the following with the 30-carbon saturated straight chain alcohol,triacontanol.Atoms other than hydrogen and oxygen are labeled.

Question 42

Which of the following would be the general structure of a phospholipid?

A)
B)
C)
D)All of these could be a phospholipid depending on the identity of the R groups.

Question 43

Which of the following would have the highest melting point? Atoms other than carbon and hydrogen are labeled.

A)
B)
C)
D)All have about the same melting point.

Question 44

Describe how a micelle and cell membrane are similar.

Question 45

Which of the following correctly does not correctly describe the composition of a phosphatidylethanolamine?

A)Glycerol residue
B)Phosphate group
C)One fatty acid residue
D)Ethanolamine residue
E)All of the above

Question 46

The following compound could be classified as all of the following except which one? ​ ​

A)Phospholipid
B)Glycerophosopholipid
C)Sphingomyelin
D)Phosphodiester

Question 47

The following generalized structure is that of a:

A)prostaglandin
B)thromboxane
C)leukotriene

Question 48

Which of the following is common to both glycerophospholipids and sphingomyelins?

A)Phosphatidic acid
B)Sphingosine
C)Phosphate
D)Choline

Question 49

Which of the following types/classes of compounds are derived from the following structure?

A)Thromboxanes
B)Leukotrienes
C)Prostaglandins
D)Eicosanoids
E)All are derived from this structure.

Question 50

Examine the following structure.Atoms other than carbon and hydrogen are labeled. This substance:

A)is a saturated fatty acid.
B)would be found in animal fat.
C)could react with glycerol to form a triacylglycerol.
D)could react with a long chain alcohol to form a wax.
E)All of the above characterize this structure.

Question 51

Examine the following structure.Atoms other than carbon and hydrogen are labeled. Which of the following does not characterize this structure?

A)Polyunsaturated fatty acid
B)Cis fatty acid
C)Omega-6 fatty acid
D)Essential in the human diet
E)All of the above characterize this structure.

Question 52

Write the saponification reaction of glyceryl monooleate distearate with aqueous NaOH.

Question 53

Which feature is common to all lipids?

A)Contain carbonyl groups
B)Fused rings
C)Polar character
D)Solubility in nonpolar solvents
E)Ester linkages

Question 54

Classify the following structure.

A)wax
B)fat
C)oil
D)soap