Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
expand_more
expand_more
format_list_bulleted
Question
Chapter 5, Problem 5.68P
Interpretation Introduction
Interpretation: The models of compound A and compound B are to be drawn and the given observation is to be explained. The allene in mycomycin is to be located and whether mycomycin is chiral or achiral is to be determined.
Concept introduction: Allenes are the compounds in which two adjacent double bonds share common carbon atom. These are also known as cumulative dienes. Cumulative dienes are different from conjugated dienes because conjugated dienes comprise double bonds separated by one single bond.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
30. How many chirality centers exist on the following molecule?
A. 4
B. 5
C. 6
D. 7
1. What is the relationship between the following two compounds?
a.stereoisomersb.identicalc.constitutional isomers
2. Assign the absolute configuration of the chirality center as R or S.
Because there is usually slow interconversion between the two isomeric forms at room temperature.
Because there is usually rapid interconversion between the two isomeric forms at room temperature.
Because chirality only exists with the tetrahedral carbon atoms.
Because four bonds a are needed to define a stereogenic center.
Chapter 5 Solutions
Organic Chemistry
Ch. 5 - Prob. 5.1PCh. 5 - Prob. 5.2PCh. 5 - Draw the mirror image of each compound. Label each...Ch. 5 - Prob. 5.4PCh. 5 - Prob. 5.5PCh. 5 - Prob. 5.6PCh. 5 - The facts in section 5.4A can be used to locate...Ch. 5 - Prob. 5.8PCh. 5 - Prob. 5.9PCh. 5 - Prob. 5.10P
Ch. 5 - Prob. 5.11PCh. 5 - Prob. 5.12PCh. 5 - Label each compound as R or S.Ch. 5 - Prob. 5.14PCh. 5 - Prob. 5.15PCh. 5 - Prob. 5.16PCh. 5 - Prob. 5.17PCh. 5 - Prob. 5.18PCh. 5 - Prob. 5.19PCh. 5 - Prob. 5.20PCh. 5 - Prob. 5.21PCh. 5 - Prob. 5.22PCh. 5 - Prob. 5.23PCh. 5 - Which of the following cyclic molecules are meso...Ch. 5 - Prob. 5.25PCh. 5 - Prob. 5.26PCh. 5 - The amino acid (S)-alanine has the physical...Ch. 5 - Prob. 5.28PCh. 5 - Prob. 5.29PCh. 5 - Prob. 5.30PCh. 5 - Prob. 5.31PCh. 5 - Prob. 5.32PCh. 5 - Prob. 5.33PCh. 5 - Prob. 5.34PCh. 5 - Prob. 5.35PCh. 5 - Prob. 5.36PCh. 5 - Prob. 5.37PCh. 5 - Determine if each compound is identical to or an...Ch. 5 - Prob. 5.39PCh. 5 - Locate the stereogenic centers in each compound. A...Ch. 5 - Prob. 5.52PCh. 5 - Prob. 5.41PCh. 5 - Prob. 5.42PCh. 5 - Prob. 5.43PCh. 5 - Prob. 5.44PCh. 5 - Prob. 5.45PCh. 5 - Label each stereogenic center as R or S. a. c. e....Ch. 5 - Prob. 5.47PCh. 5 - Prob. 5.48PCh. 5 - Prob. 5.49PCh. 5 - Prob. 5.50PCh. 5 - Prob. 5.51PCh. 5 - Prob. 5.53PCh. 5 - Prob. 5.54PCh. 5 - Prob. 5.55PCh. 5 - Draw all possible stereoisomers for each...Ch. 5 - Prob. 5.57PCh. 5 - 5.59 Explain each statement by referring to...Ch. 5 - Prob. 5.59PCh. 5 - Prob. 5.60PCh. 5 - Prob. 5.61PCh. 5 - Prob. 5.62PCh. 5 - Prob. 5.63PCh. 5 - Prob. 5.64PCh. 5 - Prob. 5.65PCh. 5 -
5.67 Artemisinin and mefloquine are widely used...Ch. 5 - 5.68 Saquinavir (trade name Invirase) is a...Ch. 5 - Prob. 5.68PCh. 5 - Prob. 5.69PCh. 5 - Prob. 5.70PCh. 5 - Prob. 5.71PCh. 5 - Problem 5.73 An acid-base reaction of with a...
Knowledge Booster
Similar questions
- Molnupiraviris a promising drug candidate that is discovered to treat patients with Covid-19. The drug is more advantageous than Remdesivir because it is administered orally. The structure of Molnupiraviris drawn below: *Figure in the screenshot* a. How many chirality centers exist on this drug? b. How many maximum numbers of stereoisomers with respect to chiral centers exist? c. Determine R/S configuration of each chiral centeronMolnupiravirby pointing to each chiral center with an arrow on the structure above d. Draw the enantiomer of Molnupiraviracross from it above e. MolnupiravirdestroysCorona virus by introducing error during viral RNA replication. If you were a physician, would you administer a pill that consists of a racemic mixture of Molnupiravirand its enantiomer to a covid positive patient? What would be your expectations? Give your reasons.arrow_forward1. Consider the following pairs of structures. Designate each chirality center as (R) or (5) and identify the relationship between them by describing them as representing enantiomers, diastereomers, constitutional isomers, or two molecules of the same compound. Use handheld molecular models to check your answers. HG (a) Br and and CH H,G H (b) and CH, Br Br 'F (k) and Br CI Br (e) and CH, CH, CH CH, CH, H- -H- CH and H- -Br (d) and FCH CH, CH, Br H CH, and (m) (e) and H. Br CH, and (m) and Br CH (o) and nd and and andarrow_forward) How many chiral centers are present in desosamine? How many stereoisomers are possible for it? How many pairs of enantiomers are possible for it?arrow_forward
- Find an example of a chiral molecule in biology whose enantiomers have markedly different functions. Where is the chiral center located, and how can it be identified? Find and include an image of its molecular structure. What function does the active enantiomer play biologically, and how is this function hindered or changed with the other enantiomer? Are there any synthetic considerations for this molecule?arrow_forwardA limited number of chiral compounds having no stereogenic centersexist. For example, although A is achiral, constitutional isomer B ischiral. Make models and explain this observation. Compoundscontaining two double bonds that share a single carbon atom are calledallenes. Locate the allene in the antibiotic mycomycin and decidewhether mycomycin is chiral or achiral.arrow_forwardJj.152.arrow_forward
- a) How many chiral centers exist in the following molecule structure A? b) How many possible stereoisomers would exist for structure A (including structure A) based on the correct number of chiral centersarrow_forwardIs methane chiral or achiral? Why? Give an example of an everyday object that is chiral and one that is achiral.arrow_forwardA. Give your comment(s) on the following questions below: 1. Are all chiral molecules enantiomers? Why or why not? 2. What is the difference between enantiomers and diastiomers ? 3. What are the differences between stereoisomers, structural isomers and constitutional isomers?arrow_forward
- 1. How many chiral centers available in this compound: а. 1 CH3 b. 2 с. 3 H CH3 d. 4 OCH3 2. How many stereoisomers are possible for the above compound in question 1: b. 2 с. 3 d. 4 a. 1arrow_forward1. Which of the following molecules are chiral? Identify the chirality center(s) in each. (a) -CH3 (b) -CH2CH2CH3 (c) CH3CH2 Toluene Coniine (from poison hemlock) H. Phenobarbital (tranquilizer) 2. A 1.50 g sample of coniine, the toxic extract of poison hemlock, was dissolved in 10.0 mL of ethanol and placed in a sample cell with a 5.00 cm pathlength. The observed rotation at the sodium D line was +1.21°. Calculate [a]p for coniine. 3. Rank the substituents in each of the following sets: (а) -Н, -ОН, -CH-CH3, -СH>СH,ОН (b) -СО-Н, -СО,CH3, -СH2ОH, -он (c) -CN, -CH2NH2, -CH2NHCH3, –NH2 (d) –SH, –CH2SCH3, –CH3, –SSCH3 4. Assign R,S configurations to the following molecules: (a) Br (b) H (c) NH2 H3C-CO2H HOC-CO2H CH3 NCC-CH3 H H 5. Assign R or S configuration to each chirality center in the following molecules: (a) Br (b) CH3 CH3 HaBr (c) HaCH3 BraH H3C" OH H CH3 OH CH3 OH Which of these compounds are enantiomers, and which are diastereomers? 6. Which of the following substances have meso…arrow_forwardaarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Macroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks Cole
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Brooks Cole