Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
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.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
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.
OH OH O
OH-C-C-C-C-OH
H H
Tartaric acid, shown above, is a dihydroxycarboxylic acid. How many chiral centers does it
possess?
OA) 0
OB) 1
Oc) 2
OD) 3
O E) 4
Which, if any, of the following are geometric isomers?
28
étv
Aa
MacBook Air
DII
F2
F3
F4
F5
F6
F7
F8
F9
F10
@
%23
$
%
&
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
Chapter 27 Solutions
Organic Chemistry
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...
Additional Science Textbook Solutions
Find more solutions based on key concepts
Determine [OH], [H+], and the pH of each of the following solutions. a. 1.0 M KCl b. 1.0 M KC2H3O2
Chemistry
141. Design a device that uses as electrochemical cell to determine amount of
in a sample water Describe, in...
Chemistry: Structure and Properties (2nd Edition)
Determine [OH], [H+], and the pH of each of the following solutions. a. 1.0 M KCl b. 1.0 M KC2H3O2
Chemistry
Practice Problem ATTEMPT
Write the rate expressions for each of the following reactions:
(a)
(b)
(c)
Chemistry
Describe the orbitals used in bonding and the bond angles in the following compounds: a. CH3O b. CO2 c. H2CO d....
Organic Chemistry (8th Edition)
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 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)CH3arrow_forwardClassify the structures as being either an enantiomer, diastereomer or diastereomer/epimer of D-glucose. Structure A: CH H- -OH Structure B: но- H- H- OH Structure C: H- он H- -H D-Glucose: OH || CH CH CH он H- он но -H H- он но он но но- H- но H- OH OH но -- H- -H H -Ç-H Structure A: OH Structure B: OH Structure C: OHarrow_forwardTwo sugars differing in configuration at a single asymmetric carbon atom are known as epimers. D-mannose is a C-2 epimer of glucose (Structure I), while D-galactose is a C-4 epimer of glucose. Structure Il and IIl are H- -OH но- -H H OH HO H но- H HO H H -OH H- -OH HO OH H -OH H- -OH H OH HO. HO, OH II II Which of the following represents an aldopentose? OH H O HO O HO H но н HO H но- HO H HO H HO- H OH H OH H OH H OH OH HO Он of но" HO O OH он III IV These are chemical messengers that are secreted by endocrine glands and carried through the bloodstream to target tissues. prostaglandin deoxysugar glycoside hormones Which of the following is NOT correctly paired? cellulose: beta-1,4-glycosidic linkage amylose: alpha-1,4-glycosidic linkage chitosan: alpha-1,4-glycosidic linkage cellubiose: beta-1,4-glycosidic linkagearrow_forward
- (d) Draw the structure of the expected product when monosaccharide B undergo mutarotation upon dissolving in water in the presence of Tollens reagent (AGNO3, NHẠOH). он OH O. OH OH OH monosaccharide Barrow_forward4. Identify the component monosaccharides of each of the following compounds and describe the type of glycosidic linkage in each. Но он Но OH HO он Но- Но- (a) OH (c) CH,OHO. (b) CH2OHO Lon OH HO H ČHOH H OH ÓH ОНarrow_forwardDraw and name the seven aldehydes and ketones with the formula C5H10O. Which are chiral?arrow_forward
- 17-74 Glucose, C6H12O6, contains an aldehyde group but exists predominantly in the form of the cyclic hemiacetal shown here. We will discuss this cyclic form of glucose in Chapter 20. A cyclic hemiacetal is formed when the —OH group of one carbon bonds to the carbonyl group of another carbon. (a) Which carbon in glucose provides the —OH group and which provides the —CHO group? (b) Draw the alternative chair confirmations of D-glucose and state which of the two is the more stable.arrow_forward15-30 (Chemical Connections 15A) What does it mean to say that a drug is chiral? If a drug is chiral, will it be optically active? That is, will it rotate the plane of polarized light?arrow_forwardEleostearic acid, C18H30O2, is a rare fatty acid found in the tung oil used for finishing furniture. On ozonolysis followed by treatment with zinc, eleostearic acid furnishes one part pentanal, two parts glyoxal (OHC-CHO), and one part 9-oxononanoic acid [OHC(CH2)7CO2H]. What is the structure of eleostearic acid?arrow_forward
- D The following disaccharide contains a(n) (blank]-glycosidic linkage. HO CH₂OH ОН Oa-1,4 OB-1,4 a-1,6 O B-1,6 0 OH Question 6 double bond ssignments/syllabus ester bond ether bond amide bond HO A glycosidic bond between two monosaccharides can also be classified as a(n) [blank). OH OH Melebi OH MacBook Proarrow_forwardThe amino acid threonine has two chiral centers. The stereoisomer found in proteins has the configuration 2S,3R about the two chiral centers. Draw (a) a Fischer projection of this stereoisomer and (b) a three-dimensional representationarrow_forwardO O NaOME, HOMearrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Chapter 4 Alkanes and Cycloalkanes Lesson 2; Author: Linda Hanson;https://www.youtube.com/watch?v=AL_CM_Btef4;License: Standard YouTube License, CC-BY
Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License