Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 25, Problem 47P
Interpretation Introduction
Interpretation:
The possible structure of A and B should be identified from the given reaction sequence.
Concept introduction:
Ozonolysis:
Ozonolysis is a oxidising agent when
Dimethyl sulphide is used as reducing work up in the reaction.
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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.
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Chapter 25 Solutions
Organic Chemistry (8th Edition)
Ch. 25.1 - Prob. 1PCh. 25.3 - Which has a higher melting point, glyceryl...Ch. 25.3 - Draw the structure of an optically inactive fat...Ch. 25.3 - Draw the structure of an optically active fat...Ch. 25.5 - Do the identities of R1 and R2 in phosphatidic...Ch. 25.5 - Membranes contain proteins, Integral membrane...Ch. 25.5 - Prob. 8PCh. 25.5 - The membrane phospholipids in deer have a higher...Ch. 25.6 - Treating PGC2 with a strong base such as sodium...Ch. 25.7 - Mark off the isoprene units in menthol, -selinene,...
Ch. 25.7 - Prob. 13PCh. 25.7 - Prob. 14PCh. 25.8 - Propose mechanisms for the Claisen condensation...Ch. 25.8 - Prob. 16PCh. 25.8 - Propose a mechanism for the conversion of...Ch. 25.8 - Propose a mechanism for the biosynthesis of...Ch. 25.8 - Propose a mechanism for the conversion of the E...Ch. 25.8 - The fluoro-substitued geranyl pyrophosphate shown...Ch. 25.8 - Prob. 22PCh. 25.8 - Prob. 23PCh. 25.9 - Draw the individual 1,2-hydride and 1,2-methyl...Ch. 25.10 - Prob. 26PCh. 25.10 - Prob. 27PCh. 25.10 - The acid component of a cholesterol ester is a...Ch. 25.10 - Prob. 29PCh. 25.10 - Prob. 30PCh. 25 - Prob. 31PCh. 25 - An optically active fat, when completely...Ch. 25 - Prob. 33PCh. 25 - a. How many different triacylglycerols are there...Ch. 25 - Cardiolipins are found in heart muscles. Draw the...Ch. 25 - Nutmeg contains a simple, fully saturated...Ch. 25 - Draw the product that is obtained from the...Ch. 25 - Prob. 39PCh. 25 - Prob. 40PCh. 25 - Propose a mechanism for the biosynthesis of...Ch. 25 - 5-Androstene-3.17-dione is isomerized to...Ch. 25 - Prob. 44PCh. 25 - Eudesmol is a sesquiterpene found in eucalyptus....Ch. 25 - Prob. 46PCh. 25 - Prob. 47PCh. 25 - Diethylstilbestrol (DES) was given to pregnant...
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- Alcohol A (C10H18O) is converted to a mixture of alkenes B and C on being heated with potassium hydrogen sulfate (KHSO4). Catalytic hydrogenation of B and C yields the same product. Assuming that dehydration of alcohol A proceeds without rearrangement, deduce the structures of alcohol A and alkene C.arrow_forwardCompound A (C11H23Br) is a secondary alkyl halide. On being heated with a solution of sodium ethoxide in ethanol, compound A yielded a mixture of two alkenes B and C, each having molecular formula C11H22. Catalytic hydrogenation of the major isomer B or the minor isomer C gave only 3,5-diethylheptane. Draw structures for compounds A, B, and C consistent with these observations.arrow_forwardA, a compound with molecular formula C6H10, contains three methylene units. A reacts with one equivalent of H2 over Pd/C to yield B. A reacts with aqueous acid to form a single product, C, and undergoes hydroboration/oxidation to form a pair of enantiomers, D and E. Ozonolysis of A followed by reaction with dimethyl sulfide forms F with molecular formula C6H10O2. Provide structures for A–F.arrow_forward
- Compound A (C6H12O2) reacts with water, acid, and heatto yield compound B (C5H10O2) and compound C (CH4O).Compound B is acidic. Deduce possible structures of compounds A, B, and Carrow_forwardCompound A has the formula C8H8. It reacts rapidly with KMN04 to give CO2 and a carboxylic acid, B (C7H602), but reacts with only 1 molar equivalent of H2 on catalytic hydrogenation over a palladium catalyst. On hydrogenation under conditions that reduce aromatic rings, 4, equivalents of H2 are taken up and hydrocarbon C (C8H16) is produced. What are the structures of A, B, and C. .CO.H COH A A B C OH A CO2H A B QUESTION 6arrow_forwardCompound 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_forward
- An unknown hydrocarbon A with the formula C6H10 reacts with 1 molar equivalent of H2 over a palladium catalyst to give B C6H12 (Rxn 1). Hydrocarbon A also reacts with OsO4 to give the glycol C (Rxn 2). A gives 5-oxohexanal on ozonolysis (Rxn 3). Draw the structures of A, B, and C. Give the reactions.arrow_forwardCompound W has molecular formula C₁4H18 and reacts with H₂ to form X. Oxidative cleavage of W with O3 followed by CH3 SCH3 affords Y. What is the structure of W?arrow_forwardOn being heated with a solution of sodium ethoxide in ethanol, compound A (C7H15Br) yielded a mixture of two alkenes B and C, each having the molecular formula C7H14. Catalytic hydrogenation of the major isomer B or the minor isomer C gave only 3-ethylpentane. Suggest structures for compounds A, B, and C consistent with these observations.arrow_forward
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