Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 11, Problem 32P
What compound of molecular formula
What two compounds of molecular formula
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Compound A has the molecular formula C14H25Br and was obtained by reaction of sodium acetylide (HC≡CNa) )with 1,12-dibromododecane. On treatment of compound A with sodium amide, it was converted to compound B (C14H24). Ozonolysis of compound B gave the diacid HO2C(CH2)12CO2H. Catalytic hydrogenation of compound B over Lindlar palladium gave compound C (C14H26), while hydrogenation over platinum gave compound D (C14H28). Sodium-ammonia reduction of compound B gave compound E (C14H26). Both C and E yielded O═CH(CH2)12CH═O on ozonolysis. Assign structures to compound A through E so as to be consistent with the observed transformations.
(a) Chromic acid oxidation of 4-tert-butyl-1,2-dimethylbenzene yielded a single compound having the molecular formula C12H14O4. What was this compound?(b) What product is expected from chromic acid oxidation of 2,3-dihydroindene?
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 11 Solutions
Organic Chemistry - Standalone book
Ch. 11.1 - Prob. 1PCh. 11.1 - Prob. 2PCh. 11.2 - The two compounds shown differ by a factor of 60...Ch. 11.2 - Prob. 4PCh. 11.2 - Prob. 5PCh. 11.2 - Prob. 6PCh. 11.3 - Prob. 7PCh. 11.3 - Prob. 8PCh. 11.3 - Evaluate 2,3,3-trimethyl-1-butene as a candidate...Ch. 11.4 - After heating a solution of allyl tert-butyl...
Ch. 11.5 - Prob. 11PCh. 11.6 - Prob. 12PCh. 11.8 - Prob. 13PCh. 11.9 - What dienes containing isolated double bonds are...Ch. 11.10 - Prob. 15PCh. 11.10 - Prob. 16PCh. 11.11 - Prob. 17PCh. 11.12 - Dicarbonyl compounds such as quinones are reactive...Ch. 11.12 - 2,3-Di-tert-butyl-1,3-butadiene is extremely...Ch. 11.12 - Methyl acrylate (H2C=CHCO2CH3) reacts with...Ch. 11.13 - Prob. 21PCh. 11.14 - What diene and dienophile could you use to prepare...Ch. 11.14 - Write equations in the synthetic direction for the...Ch. 11.16 - Prob. 24PCh. 11.16 - Prob. 25PCh. 11 - Write structural formulas for each of the...Ch. 11 - Give an acceptable IUPAC name for each of the...Ch. 11 - A certain species of grasshopper secretes an...Ch. 11 - Which of the following are chiral?...Ch. 11 - Describe the molecular geometry expected for...Ch. 11 - Prob. 31PCh. 11 - What compound of molecular formula C6H10 gives...Ch. 11 - Prob. 33PCh. 11 - Prob. 34PCh. 11 - Prob. 35PCh. 11 - Prob. 36PCh. 11 - Identify the more reactive dienophile in each of...Ch. 11 - Prob. 38PCh. 11 - Prob. 39PCh. 11 - Prob. 40PCh. 11 - Prob. 41PCh. 11 - Prob. 42PCh. 11 - Prob. 43PCh. 11 - Prob. 44PCh. 11 - Prob. 45PCh. 11 - Prob. 46PCh. 11 - Show how to prepare each of the following...Ch. 11 - Prob. 48PCh. 11 - Prob. 49PCh. 11 - Prob. 50PCh. 11 - Compound A was converted to compound B by the...Ch. 11 - Suggest reasonable explanations for each of the...Ch. 11 - Prob. 53PCh. 11 - Prob. 54PCh. 11 - Prob. 55DSPCh. 11 - Prob. 56DSPCh. 11 - Prob. 57DSPCh. 11 - Prob. 58DSPCh. 11 - Prob. 59DSP
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