ORGANIC CHEMISTRY-EBOOK>I<
9th Edition
ISBN: 9781305084414
Author: McMurry
Publisher: INTER CENG
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Textbook Question
Chapter 27.6, Problem 9P
Lithocholic acid is an A–B cis steroid found in human bile. Draw lithocholic acid showing chair conformations, as in Figure 27-11, and tell whether the hydroxyl group at C3 is axial or equatorial.
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27. Which of the following statements about cholesterol is not correct?
CH3
CH3
H.
d
но
Cholesterol
(a) Cholesterol is a steroid that contains a tetracyclic ring system.
(b) Cholesterol is a steroid that contains 8 chiral carbons and can form 28 or 256 stereoisomers.
(c) Each atom or group attached to a ring-junction carbon (i.e., carbons a -e) is in a trans or axial
position. Because of this the tetracyclic ring system is mostly flat.
(d) Cholesterol is used to synthesized vitamin D, bile acids, sex hormones, and adrenocorticoid
hormones.
(e) Cholesterol is not found in the cell membranes of animals.
2. The following diagram shows the straight-chain structure of an N-acetyl aminoheptose that is found in certain plants including avocado (Persea Americana).
CHOH
CH2OH
CH,OH
O:
O:
HO-
но
-HO-
HO H
но
-HO-
H-
NHAC
NHAC
ACHN
OH HN
H-
HO-
HO
CH2OH
CHOH
CH20H
HO
HO.
Structure B
Structure C
Structure A
OH
OH
CHOH
CH2OH
CH OH
HO H
HO H
HO-
H OH
HO-
HO
H-
-NHAC
ACHN-
ACHN
HO-
H OH
HO
ČHOH
CH2OH
CH2OH
Structure D
Structure E
Structure F
Which of the Fischer projections (A-F) matches the skeletal formula shown?
Structure A
Structure B
Structure C
Structure D
Structure E
O Structure F
(1 mark)
王
HI
Draw all the possible stereoisomerism for following structures. Label the chiral centre
with an asterisk (*) if any.
(a)
CНICOОH)(NH)CH-COOH
(b)
(CH3)2C=C(COOH)CH(NO2)CH3
Chapter 27 Solutions
ORGANIC CHEMISTRY-EBOOK>I<
Ch. 27.1 - Carnauba wax, used in floor and furniture...Ch. 27.1 - Draw structures of glyceryl tripalmitate and...Ch. 27.2 - Prob. 3PCh. 27.2 - Write the saponication reaction of glyceryl...Ch. 27.4 - Prob. 5PCh. 27.5 - Prob. 6PCh. 27.5 - Prob. 7PCh. 27.6 - Draw the following molecules in chair...Ch. 27.6 - Lithocholic acid is an A–B cis steroid found in...Ch. 27.7 - Prob. 10P
Ch. 27.SE - Prob. 11VCCh. 27.SE - Propose a biosynthetic pathway for the...Ch. 27.SE - Identify the following fatty acid, and tell...Ch. 27.SE - Prob. 14MPCh. 27.SE - Prob. 15MPCh. 27.SE - Prob. 16MPCh. 27.SE - Prob. 17APCh. 27.SE - Fats can be either optically active or optically...Ch. 27.SE - Prob. 19APCh. 27.SE - Show the products you would expect to obtain from...Ch. 27.SE - Draw a Newman projection along the C2-C3 bond of...Ch. 27.SE - The plasmalogens are a group of lipids found in...Ch. 27.SE - Prob. 23APCh. 27.SE - Prob. 24APCh. 27.SE - Prob. 25APCh. 27.SE - Prob. 26APCh. 27.SE - Prob. 27APCh. 27.SE - Prob. 28APCh. 27.SE - Prob. 29APCh. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Prob. 34APCh. 27.SE - Draw the most stable chair conformation of...Ch. 27.SE - Draw the most stable chair conformation of...Ch. 27.SE - Prob. 37APCh. 27.SE - Prob. 38APCh. 27.SE - Prob. 39APCh. 27.SE - What product would you obtain by reduction of...Ch. 27.SE - Prob. 41APCh. 27.SE - Eleostearic acid, C18H30O2, is a rare fatty acid...Ch. 27.SE - Prob. 43APCh. 27.SE - Prob. 44APCh. 27.SE - Propose a synthesis of diethylstilbestrol (Problem...Ch. 27.SE - Prob. 46APCh. 27.SE - Cembrene, C20H32, is a diterpenoid hydrocarbon...Ch. 27.SE - α-Fenchone is a pleasant-smelling terpenoid...Ch. 27.SE - Prob. 49APCh. 27.SE - Propose a mechanism for the biosynthesis of the...
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