Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 19, Problem 19.58AP
Interpretation Introduction
Interpretation:
The compounds A, B, and C from the given reaction observation are to be stated.
Concept introduction:
In
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Propylene oxide is a chiral molecule. Hydrolysis of propylene oxide gives propylene glycol, another chiral molecule.
A. Provide a mechanism for the acid-catalyzed hydrolysis of pure (R)-propylene oxide (treatment with H2SO4/H2O), showing the correct stereochemistry.
B. Provide a mechanism for the treatment of pure (R)-propylene oxide with NaOH in water (base-catalyzed hydrolysis), showing the correct stereochemistry.
C. Explain why acid-catalyzed hydrolysis of optically active propylene oxide gives a product with a rotation in the opposite direction from the product of the base catalyzed hydrolysis.
Write out all the isomers of the compound with molecular formula C4H10O
Select the normal/ primaryisomer and treat it with conc. H2SO4 and heat. Identify the reaction and give the product ‘A’ from it.
Treatment of ‘A’ with HCl/H2O gives ‘B’
Treatment of ‘A’ with cold KMnO4/ -OH gives ‘C’
Treatment of ‘A’ with Hot KMnO4/-OH gives ‘D’ followed by acidification of the mixture to give ‘E’
A certain compound of molecular formula C19H38 was isolated from fish oil and from plankton. On hydrogenation it gave 2,6,10,14-tetramethylpentadecane. Ozonolysis gave (CH3)2C O and a 16-carbon aldehyde. What is the structure of the natural product? What is the structure of the aldehyde?
Chapter 19 Solutions
Organic Chemistry
Ch. 19 - Prob. 19.1PCh. 19 - Prob. 19.2PCh. 19 - Prob. 19.3PCh. 19 - Prob. 19.4PCh. 19 - Prob. 19.5PCh. 19 - Prob. 19.6PCh. 19 - Prob. 19.7PCh. 19 - Prob. 19.8PCh. 19 - Prob. 19.9PCh. 19 - Prob. 19.10P
Ch. 19 - Prob. 19.11PCh. 19 - Prob. 19.12PCh. 19 - Prob. 19.13PCh. 19 - Prob. 19.14PCh. 19 - Prob. 19.15PCh. 19 - Prob. 19.16PCh. 19 - Prob. 19.17PCh. 19 - Prob. 19.18PCh. 19 - Prob. 19.19PCh. 19 - Prob. 19.20PCh. 19 - Prob. 19.21PCh. 19 - Prob. 19.22PCh. 19 - Prob. 19.23PCh. 19 - Prob. 19.24PCh. 19 - Prob. 19.25PCh. 19 - Prob. 19.26PCh. 19 - Prob. 19.27PCh. 19 - Prob. 19.28PCh. 19 - Prob. 19.29PCh. 19 - Prob. 19.30PCh. 19 - Prob. 19.31PCh. 19 - Prob. 19.32PCh. 19 - Prob. 19.33PCh. 19 - Prob. 19.34PCh. 19 - Prob. 19.35PCh. 19 - Prob. 19.36PCh. 19 - Prob. 19.37PCh. 19 - Prob. 19.38PCh. 19 - Prob. 19.39PCh. 19 - Prob. 19.40APCh. 19 - Prob. 19.41APCh. 19 - Prob. 19.42APCh. 19 - Prob. 19.43APCh. 19 - Prob. 19.44APCh. 19 - Prob. 19.45APCh. 19 - Prob. 19.46APCh. 19 - Prob. 19.47APCh. 19 - Prob. 19.48APCh. 19 - Prob. 19.49APCh. 19 - Prob. 19.50APCh. 19 - Prob. 19.51APCh. 19 - Prob. 19.53APCh. 19 - Prob. 19.54APCh. 19 - Prob. 19.55APCh. 19 - Prob. 19.56APCh. 19 - Prob. 19.57APCh. 19 - Prob. 19.58APCh. 19 - Prob. 19.59APCh. 19 - Prob. 19.60APCh. 19 - Prob. 19.61APCh. 19 - Prob. 19.62APCh. 19 - Prob. 19.63APCh. 19 - Prob. 19.64APCh. 19 - Prob. 19.65APCh. 19 - Prob. 19.66APCh. 19 - Prob. 19.67APCh. 19 - Prob. 19.68APCh. 19 - Prob. 19.69APCh. 19 - Prob. 19.70APCh. 19 - Prob. 19.71APCh. 19 - Prob. 19.72AP
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
- Compound A has the formula C9H19Cl. B is a C9H19Br compound.A and B undergo base-promoted E2 elimination to give the same alkene C as the major product as well as different minor products.C reacts with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2,6-dimethylheptane.Addition of HCl to C yields A as the major product.Propose structures for A and B.arrow_forwardβ-ocimene is a pleasant smelling hydrocarbon found in the leaves of a certain herbs. It has a molecular formula C10H16 and a UV absorption λmax 232nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis β-ocimene followed by the treatment with zinc and acetic acid produces the following fragments:arrow_forwardCompound X is optically inactive and has the formula C 16H 16Br 2. On treatment with strong base, X gives hydrocarbon Y, C 16H 14. Compound Y absorbs 2 equivalents of hydrogen when reduced over a palladium catalyst and reacts with ozone to give two fragments. One fragment Z, is an aldehyde with formula C 7H 6O. The other fragment is glyoxal, (CHO)2. Which of the following answers is correct? Select all that are correct.arrow_forward
- Compound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr), which reacts violently with D2O to give 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone (CH3COCH3) followed by hydrolysis gives D (C10H18O). Heating D with concentrated H2 SO4 gives E (C10 H16), which decolorizes two equivalents of Br2 to give F (C10H16 Br4). E undergoes hydrogenation with excess H2 and a Pt catalyst to give isobutylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughout.arrow_forward1. write out all the isomers of the compound with molecular formula C4H10O. 2. select the normal/primary isomer and treat it with conc.H2SO4 and heat to produce A. Identify the type of reaction 3. Treatment of A with HCl/H2O gives B and with cold KMnO4/ OH- gives C . Give the name and structures of A, B and C 4. Treatment of A with Hot KMnO4/OH- gives D followed by acidification of the mixture to give E. What is D and E ?arrow_forward-Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the molecular formula C10H16 and a UV absorption maximum at 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis of -ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments: (a) How many double bonds does -ocimene have? (b) Is -ocimene conjugated or nonconjugated? (c) Propose a structure for -ocimene. (d) Write the reactions, showing starting material and products.arrow_forward
- A step in a synthesis of PGE1 (prostaglandin E1, alprostadil) is the reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Propose a mechanism for formation of this bromolactone and account for the observed stereochemistry of each substituent on the cyclohexane ring. Alprostadil is used as a temporary therapy for infants born with congenital heart defects that restrict pulmonary blood flow. It brings about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and blood oxygenation.arrow_forwardFollowing is a retrosynthetic analysis for the synthesis of the herbicide (S)-Metolachlor from 2-ethyl-6-methylaniline, chloroacetic acid, acetone, and methanol. Show reagents and experimental conditions for the synthesis of Metolachlor from these four organic starting materials. Your synthesis will most likely give a racemic mixture. The chiral catalyst used by Novartis for reduction in Step 2 gives 80% enantiomeric excess of the S enantiomer.arrow_forwardAmines are converted into alkenes by a two-step process called Hofmann elimination. SN2 reaction of the amine with an excess of CH3I in the first step yields an intermediate that undergoes E2 reaction when treated with silver oxide as base. Pentylamine, for example, yields 1-pentene. Propose a structure for the intermediate, and explain why it readily undergoes elimination.arrow_forward
- Cembrene, C20H32, is a diterpenoid hydrocarbon isolated from pine resin. Cembrene has a UV absorption at 245 nm, but dihydrocembrene (C20H34), the product of hydrogenation with 1 equivalent of H2, has no UV absorption. On exhaustive hydrogenation, 4 equivalents of H2 react, and octahydrocembrene, C20H40, is produced. On ozonolysis of cembrene, followed by treatment of the ozonide with zinc, four carbonylcontaining products are obtained: Propose a structure for cembrene that is consistent with its formation from geranylgeranyl diphosphate.arrow_forward(R)-Pulegone is converted to (R)-citronellic acid by addition of HCl followed by treatment with NaOH. Propose a mechanism for each step in this transformation and account for the regioselectivity of HCl addition.arrow_forwardClopidogrel is the generic name for Plavix, a drug used to prevent the formation of blood clots in patients that have a history of heart attacks or strokes. A single enantiomer of clopidogrel can be prepared in three steps from the chiral αhydroxy acid A. Identify B and C in the following reaction sequence, and designate the conguration of the enantiomer formed by this route as R or S.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
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
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