Introduction To General, Organic, And Biochemistry
12th Edition
ISBN: 9781337571357
Author: Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
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.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
22:22 Tue 11 Jan
* 84%
Done
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
Classify each of the following reactions as a substitution, elimination or addition reaction:
Br
Нeat
(a)
Br2
+
HBr
Br
CN
(b)
+
CN
+
Br
Br
(c)
+
Br2
Br
Citronellol ((3R)-3,7-dimethyloct-6-en-1-ol, C10H20O) is an organic fragrance found in the oil extracted from lemon grass.
a) Name the two functional groups present in the molecule.
b) When a few drops of bromine dissolved in hexane is added to a sample of citronellol the brown colour of the bromine rapidly disappears.
i. What type of chemical reaction has occurred?
ii. Draw the structure of the product formed.
iii. Name the product.
c) The product formed when citronellol is heated with a mixture of potassium dichromate and sulfuric acid gives a yellow/orange precipitate when shaken with Brady’s reagent (2,4-dinitrophenylhydrazine). It also shows a positive result with Fehling’s solution.
i. What type of chemical reaction has occurred ?
ii. What type of functional group is present in the product?
d) Explain the type of stereoisomerism which may occur in citronellol.
Chapter 16 Solutions
Introduction To General, Organic, And Biochemistry
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
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
- Intramolecular H-bonding (IHB) are interactions that occur within one single molecule. IHB is also known as chelation, since it involves ring formation. Which of the following is (are) stabilized by IHB? * QH Çi OH -NO2 (a) Cl-Ç–Ç–H (b) či ÓH OH (с) CH, —С—СH—С—ОС,Н, CH,OH (d) | CH,OH D B Aarrow_forwardThis molecule is a(n): HC = CH – CH3 | НаС — сн — сHз O amine O alkene O alkane O etherarrow_forwardEach member of the following set of compounds is an amine; that is, each contains a nitrogen atom bonded to one, two, or three carbon groups (Section 10.4B). Which structural formulas represent the same compound, and which represent constitutional isomers? (a) (c) (e) NH₂ -on (g) (g) N|H Η 342 Chapter 11 Alkanes H-N Η (b) NH₂ (d) a NH NH₂ (f) - (h) N II H NH₂arrow_forward
- Rank the compounds in order of increasing oxidation state (most reduced to most oxidized) for the carbon atom indicated in red (C*). H3C Ο Ο Ο Ο ||| < | < || || < | < ||| || < ||| < | ||| < || < | Ö: I H H3C Ö: II :O: I H₂C H H III :O Iarrow_forwardThe structure of Corticosterone is shown here. ОН H3C НО. H3C Corticosterone DOES NOT contain: an alkene group a ketone group O an ether group O an alcohol grouparrow_forwardDraw the structure of an alkane with molecular formula C7H16 that contains (a) one 4° carbon; (b) only 1° and 2° carbons; (c) 1°, 2°, and 3° hydrogens.arrow_forward
- 11-58 (Chemical Connections 11A) How many rings in te trodotoxin contain only carbon atoms? How many contain nitrogen atoms? How many contain two oxygen atoms?arrow_forward13-38 (Chemical Connections 13A) What is meant by the term biodegradable?arrow_forward13-39 (Chemical Connections 13B) What is a carcinogen What kind of carcinogen is found in cigarette smoke?arrow_forward
- 11-63 (Chemical Connections 11C) In what way do Fre- ons negatively affect the environment?arrow_forward13-52 2,6-Di-/ezY-butyl-4-methylphenol (BHT, Section 13-4C) is an antioxidant added to processed foods to “retard spoilage.” How does BHT accomplish this goal?arrow_forward13-31 What structural features are common to vitamin E, BHT, and BHA (the three antioxidants presented in Section 13-40?arrow_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
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher: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
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Acid-Base Titration | Acids, Bases & Alkalis | Chemistry | FuseSchool; Author: FuseSchool - Global Education;https://www.youtube.com/watch?v=yFqx6_Y6c2M;License: Standard YouTube License, CC-BY