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 28, Problem 28.9P
Interpretation Introduction
Interpretation:
The structure of compound A is to be drawn which is formed by heating the given compound at
Concept introduction:
Electrocyclic reactions are pericyclic reactions which take place by concerted mechanism. These reactions involve ring opening or ring closure in a conjugated polyene.
In conrotatory reactions, the end group atomic orbital rotates in a clockwise direction.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Compound P (C2H4) which is an alkene undergoes reaction with HCl to produce compound Q (C2H5Cl). Reaction of compound Q with benzene in the presence of AlCl3 as catalyst produces compound R. Then, nitration of compound R in the presence ofnH2SO4 produces two compounds, S and T. But when compound R is reacted with a hot acidified solution of alkaline KMnO4 gives compound U. Deduce the structure of compounds P to U.
Stearolic acid, C18H32O2, yields stearic acid on catalytic hydrogenation and undergoes oxidative cleavage with ozone to yield nonanoic acid and nonanedioic acid. What is the structure of stearolic acid?
An optically active monoterpene (compound A) with molecular formula C10H18O undergoes catalytic hydrogenation to form an optically inactive compound with molecular formula C10H20O (compound B). When compound B is heated with acid, followed by reaction with O3 and then with dimethyl sulfide, one of the products obtained is 4-methylcyclohexanone. Give possible structures for compounds A and B.
Chapter 28 Solutions
Organic Chemistry
Ch. 28 - Prob. 28.1PCh. 28 - Prob. 28.2PCh. 28 - Prob. 28.3PCh. 28 - Prob. 28.4PCh. 28 - Prob. 28.5PCh. 28 - Prob. 28.6PCh. 28 - Prob. 28.7PCh. 28 - Prob. 28.8PCh. 28 - Prob. 28.9PCh. 28 - Prob. 28.10P
Ch. 28 - Prob. 28.11PCh. 28 - Prob. 28.12PCh. 28 - Prob. 28.13PCh. 28 - Prob. 28.14PCh. 28 - Prob. 28.15PCh. 28 - Prob. 28.16PCh. 28 - Prob. 28.17PCh. 28 - Prob. 28.18PCh. 28 - Prob. 28.19PCh. 28 - Prob. 28.20PCh. 28 - Prob. 28.21PCh. 28 - Prob. 28.22PCh. 28 - Prob. 28.23PCh. 28 - Prob. 28.24PCh. 28 - Prob. 28.25PCh. 28 - Prob. 28.26PCh. 28 - Prob. 28.27PCh. 28 - Prob. 28.28PCh. 28 - Prob. 28.29APCh. 28 - Prob. 28.30APCh. 28 - Prob. 28.31APCh. 28 - Prob. 28.32APCh. 28 - Prob. 28.33APCh. 28 - Prob. 28.34APCh. 28 - Prob. 28.35APCh. 28 - Prob. 28.36APCh. 28 - Prob. 28.37APCh. 28 - Prob. 28.38APCh. 28 - Prob. 28.39APCh. 28 - Prob. 28.40APCh. 28 - Prob. 28.41APCh. 28 - Prob. 28.42APCh. 28 - Prob. 28.43APCh. 28 - Prob. 28.44APCh. 28 - Prob. 28.45APCh. 28 - Prob. 28.46APCh. 28 - Prob. 28.47APCh. 28 - Prob. 28.48APCh. 28 - Prob. 28.49APCh. 28 - Prob. 28.50APCh. 28 - Prob. 28.51APCh. 28 - Prob. 28.52APCh. 28 - Prob. 28.53APCh. 28 - Prob. 28.54APCh. 28 - Prob. 28.55AP
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
- Provide the structure of the major organic product of the following reaction and? explain the stereochemistry which results in this product. 2-Pentanol reacting with 1.) PBr3, pyridine 2.) NaCNarrow_forwardAn organic compound A which has a characteristic odour is treated with 50% NaOH to give B (C7H8O)and C which is a sodium salt of an organic acid . Oxidation of B gives back A. Heating C with soda lime yields an aromatic hydrocarbon D . Deduce the structures of A,B,C and Darrow_forwardCompound A reacts with 1 molar equivalent(s) of hydrogen upon catalytic hydrogenation. A undergoes reaction with ozone, followed by Zn treatment, to give: Propose a structure for A.arrow_forward
- Several steps in the synthesis of optically active duloxetine, an antidepressant sold under the trade name Cymbalta, are shown. Identify the structure of intermediates A–C and the final product duloxetine, including stereochemistry, in this reaction sequence.arrow_forwardTwo isomers, A and B, of molecular formula C5H8 undergo catalytic hydrogenation with hydrogen gas and palladium on carbon to form the same C5H10 product. On ozonolysis followed by treatment with hydrogen peroxide (H2O2), isomer A gave a product of molecular formula C5H8O4 that has two carboxylic acid groups in it whereas isomer B gave a product of molecular formula C5H8O3 that contains a carboxylic acid group and a ketone group. Which of the following isomeric pairs best match this data?arrow_forwardTwo isomers, A and B, of molecular formula C5H8 undergo catalytic hydrogenation with hydrogen gas and palladium on carbon to form the same C5H10 product. On ozonolysis followed by treatment with hydrogen peroxide (H2O2), isomer A gave a product of molecular formula C5H8O4 that has two carboxylic acid groups in it whereas isomer B gave a product of molecular formula C5H8O3 that contains a carboxylic acid group and a ketone group. What is the isometric pair of A and B that corresponds?arrow_forward
- An organic compound A of unknown structure was found to have a molecular formula C8H16. When A was poured in water and heated, compound B having a molecular formula C8H18O was formed. B upon heating with sulfuric acid was converted to C as the major product which is identical to A. Ozonolysis of C gave one molecule each of two different products D and E, both having a molecular formula C4H8O. Write the reactions involved and determine the structure of A,B,C,D and E.arrow_forwardCompound A, C9H16 reacts with 1 molar equivalent(s) of hydrogen on catalytic hydrogenation. A undergoes reaction with ozone, followed by Zn treatment. What is the structure for A?arrow_forwardChemical compound A is an alkene that when treated with ozone followed by treatment of Zn in HOAc produces only (CH3CH2CH2) 2C = O. What is the structure of A? If A is reacted with peroxyacetic acid, what product would be obtained? Write the corresponding structure. Is this substance optically active? Please include a detailed explanation.arrow_forward
- Deduce the structure of compound C.arrow_forwardA hydrocarbon (X), with the molecular formula: C8H14 is reduced in presence of sodium and liquid ammonia to give the only product (Y) with the molecular formula: C8H16. Compounds X and Y both resulting 2,5-dimethylhexane when treated with hydrogen and platinum catalyst (H2/Pt). As a result of the oxidative cleavage of compound Y (by using KMnO4 / H2SO4), a single carboxylic acid derivative with C4H8O2 molecular formula is formed. Again, as a result of the reaction of Y with perbenzoic acid, the chiral compound C8H14O is observed, but the reaction of compound Y with bromine gives the achiral C8H14Br2 as the product.arrow_forwardGive the process of Determining the Mechanism and Stereochemistry inNucleophilic Substitution ?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
