INTRO.TO GENERAL,ORGAN...-OWLV2 ACCESS
12th Edition
ISBN: 9781337915977
Author: Bettelheim
Publisher: CENGAGE L
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Chapter 16, Problem 46P
17-54 Following is the structure of immunosuppressant FK-506, a molecule shown to disrupt calcineurin-mediated signal transduction in T-lymphocytes.
(a) There are three carbon—carbon double bonds present in this molecule. Which of the three has the potential for cis/trans isomerism? Assign a cis or trans con?guration to each carbon-carbon double bond that has this possibility.
(b) How many stereocenters are present in this molecule? How many stereoisomers are possible for it?
(c) Are there any aromatic components in this molecule?
(d) Consider the two carbon atoms marked with asterisks. Assign an R or S con?guration of each stereocenter.
(e) Because of the presence of a 21-member ring, this molecule is described as a macrocycle. This ring is fashioned by three types of bonds, several carbon-carbon bonds, one ester, one hemiacetal, and one amide. Locate the ester and the hemiacetal.
(f) Draw the structural formula of the long chain compound that would result if the hemiacetal were to be cleaved to an alcohol and a carbonyl group.
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Tamiflu®, the most effective antiviral drug used to treat avian influenza, has the following structure. Identify the indicated functional
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II
ÑH2
O 1= ketone; I| = amine; III = alkene
O 1 = ester; I| = amide; III = alkyne
O 1 = amine; || = amide; III = alkene
O 1 = amide; || = amine; III = alkene
O 1 = amine; I| = amine; III = aromatic
22:22 Tue 11 Jan
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Assignment 3 (3 of 9)
1.
Identify the functional groups in the following molecules:
(a)
(b)
(c)
H.
H
С—ОН
С-ОН
Н-С—ОН
C=C
H
H
HO-C-H
C-CH3
Н-С—ОН
Acrylic acid
(2 functional groups)
H-C-OH
Aspirin
(3 functional groups)
CH2OH
Glucose
(6 functional groups)
2.
Identify the carbon atoms in the following molecules as primary, secondary
tertiary, or quaternary:
(a)
CH3
(b)
CH3CHCH3
(c)
CH3 CH3
CH3CHCH2CH2CH3
CH3CH2CHCH2CH3
CH3CHCH,CCH3
ČH3
3.
Give IUPAC names for the following alkanes:
(a)
CH3
(b)
CH3
CH3CHCH2CH2CH3
CH3CH2ĊCH3
ČH3
(c) H3C CH3
(d)
CH2CH3 CH3
CH3CHCCH2CH2CH3
CH3CH2CHCH2CH2CHCH3
CH3
(e)
CH3 CH2CH3
(f) H3C CH3
CH3CH2CH2CHCH2CCH3
CH3C-CCH2CH2CH3
CH3
H3C CH3
4.
Draw structures for the following substances:
(a) 2-Methylheptane
(c) 4-Ethyl-3,4-dimethyloctane
(e) 1,1-Dimethylcyclopentane
(b) 4-Ethyl-2-methylhexane
(d) 2,4,4-Trimethylheptane
(f) 4-Isopropyl-3-methylheptane
(a) Draw a skeletal structure of the anabolic steroid 4-androstene-3,17-dione, also called "andro,"
from the following description. Andro contains the tetracyclic steroid skeieton with carbonyl
groups at C3 and C17, a double bond between C4 and C5, and methyl groups bonded to C10
and C13. (b) Add wedges and dashes for all stereogenic centers with the following information:
the configuration at C10 is R, the configuration at C13 is S, and all substituents at ring fusions are
trans to each other.
Chapter 16 Solutions
INTRO.TO GENERAL,ORGAN...-OWLV2 ACCESS
Ch. 16.2 - Problem 17-1 Wrtie the IUPAC name for each...Ch. 16.2 - Prob. 16.2QCCh. 16.2 - Prob. 16.3QCCh. 16.4 - Prob. 16.4QCCh. 16.4 - Prob. 16.5QCCh. 16.4 - Problem 17-6 Show the reaction of benzaldehyde...Ch. 16.4 - Problem 17-7 Identify all hemiacetals and acetals...Ch. 16.5 - Prob. 16.8QCCh. 16 - 17-9 Answer true or false. (a) The one aldehyde...Ch. 16 - Prob. 2P
Ch. 16 - 17-11 What is the difference in structure between...Ch. 16 - 17-12 Is it possible for the carbon atom of a...Ch. 16 - 17-13 Which compounds contain carbonyl groups?Ch. 16 - 17-14 Following are structural formulas for two...Ch. 16 - 17-15 Draw structural formulas for the four...Ch. 16 - Prob. 8PCh. 16 - Prob. 9PCh. 16 - 17-18 Draw structural formulas for these ketones....Ch. 16 - 17-19 Write the JUPAC names for these compounds.Ch. 16 - Prob. 12PCh. 16 - 17-2 1 Explain why each name is incorrect. Write...Ch. 16 - Prob. 14PCh. 16 - Prob. 15PCh. 16 - 17-24 In each pair of compounds, select the one...Ch. 16 - Prob. 17PCh. 16 - 17-26 Account for the fact that acetone has a...Ch. 16 - 17-27 Pentane, 1-butanol, and butanal all have...Ch. 16 - 17-28 Show how acetaldehyde can form hydrogen...Ch. 16 - 17-29 Why can’t two molecules of acetone form a...Ch. 16 - 17-30 Answer true or false. (a) The reduction of...Ch. 16 - 17-3 1 Draw a structural formula for the principal...Ch. 16 - Prob. 24PCh. 16 - 17-33 What simple chemical test could you use to...Ch. 16 - 17-34 Explain why liquid aldehydes are often...Ch. 16 - 17-35 Suppose that you take a bottle of...Ch. 16 - 17-36 Explain why the reduction of an aldehyde...Ch. 16 - Prob. 29PCh. 16 - Prob. 30PCh. 16 - Prob. 31PCh. 16 - Prob. 32PCh. 16 - Prob. 33PCh. 16 - Prob. 34PCh. 16 - Prob. 35PCh. 16 - Prob. 36PCh. 16 - Prob. 37PCh. 16 - Prob. 38PCh. 16 - 17-47 What is the characteristic structural...Ch. 16 - Prob. 40PCh. 16 - Prob. 41PCh. 16 - Prob. 42PCh. 16 - Prob. 43PCh. 16 - Prob. 44PCh. 16 - Prob. 45PCh. 16 - 17-54 Following is the structure of...Ch. 16 - Prob. 47PCh. 16 - Prob. 48PCh. 16 - Prob. 49PCh. 16 - Prob. 50PCh. 16 - Prob. 51PCh. 16 - 17-60 1-Propanol can be prepared by the reduction...Ch. 16 - Prob. 53PCh. 16 - 17-62 Show how to bring about these conversions....Ch. 16 - Prob. 55PCh. 16 - Prob. 56PCh. 16 - Prob. 57PCh. 16 - Prob. 58PCh. 16 - 17-67 Draw structural formulas for these...Ch. 16 - Prob. 60PCh. 16 - 17-69 Propanal (bp 49°C) and 1-propanol (bp 97°C)...Ch. 16 - 17-70 What simple chemical test could you use to...Ch. 16 - Prob. 63PCh. 16 - Prob. 64PCh. 16 - Prob. 65PCh. 16 - 17-72 The following molecule is an enediol; each...Ch. 16 - 17-73 Alcohols can be prepared by the...Ch. 16 - 17-74 Glucose, C6H12O6, contains an aldehyde group...Ch. 16 - Prob. 69PCh. 16 - Prob. 70PCh. 16 - Prob. 71PCh. 16 - 17-78 Complete the following equation for these...Ch. 16 - 17-79 Write an equation for each conversion. (a)...Ch. 16 - Prob. 74P
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