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 28P
A certain species of grasshopper secretes an allenic substance of molecular formula
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The following is a structural diagram for penicillin G, an antibiotic compound with outstanding antibacterial activity. It is obtained from the
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HO H H H
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Compounds Y and Z both have the formula C₂H18.
Both Y and Z react with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2-methyloctane.
The heat of hydrogenation of Y is less than that of Z.
Y and Z each undergo hydroboration/oxidation to give a primary alcohol (OH attached to a primary carbon).
What is the structure of Y?
• In cases where there is more than one answer, just draw one.
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Reaction of butane (CH 3CH 2CH 2CH 3) with Cl 2 in the presence of light forms two different alkyl chlorides that have molecular formula C 4H 9Cl. Draw the structures of both alkyl chlorides.
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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- Compounds X and Y have the formula C6H₁2. Both X and Y react with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2-methylpentane. The heat of hydrogenation of X is less than that of Y. X and Y react with HBr to form a mixture of the same bromoalkanes, and they both undergo hydroboration/oxidation to give a mixture of the same alcohols. What is the structure of Y? • In cases where there is more than one answer, just draw one. MAVI Sn [F ? ChemDoodlearrow_forwardCompounds X and Y have the formula C6H12. Both X and Y react with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2-methylpentane. The heat of hydrogenation of X is less than that of Y. X and Y react with HBr to form a mixture of the same bromoalkanes, and they both undergo hydroboration/oxidation to give a mixture of the same alcohols. What is the structure of Y? • In cases where there is more than one answer, just draw one. + ChemDoodlearrow_forwardCompounds A and B are isomers of the molecular formula C9H19Br. Both yield the same alkene C in an elimination reaction. Hydrogenation of C yields the product 2,3,3,4 tetramethyl pentane. What are the structures of A, B, and C?arrow_forward
- Vanillin, C8H8O3, is the active ingredient in vanilla flavoring. It contains a six-membered aromatic ring with an aldehyde group on carbon 1, an alkoxy group (ether) on carbon 3, and a hydroxyl group (alcohol) on carbon 4. Draw the structure of vanillin.arrow_forwardOne mole of an unknown hydrocarbon, compound C, in the presence of a platinum catalyst, adds 98.9 L of hydrogen, measured at 744 mm Hg and 22 degrees C , to form a saturated alkane which contains one ring. When one mole of compound C is reacted with ozone, followed by reduction with (CH3)2S , four moles of only one product was formed, whose condensed molecular formula is CHO -CHO. Give the structure of compound C. Explain your reasoningarrow_forwardHydrocarbon X has the formula C6H12.X reacts with one molar equivalent of hydrogen in the presence of a palladium catalyst to form a product having 12 primary hydrogens.Treatment of X with ozone followed by zinc in aqueous acid gives a mixture two aldehydes.What is the structure of X?arrow_forward
- Compound A has the molecular formula C7H12. Hydrogenation of compound A produces 2-methylhexane. Hydroboration-oxidation of compound A produces an aldehyde. Draw the structure of compound A.arrow_forwardDraw the structures of the following molecules: (a) Biacetyl, C4H6O2, a substance with the aroma of butter; it contains no rings or carbon-carbon multiple bonds. (b) Ethylenimine, C2H5N, a substance used in the synthesis of melamine polymers; it contains no multiple bonds. (c) Glycerol, C3H8O3, a substance isolated from fat and used in cosmetics; it has an -OH group on each carbon.arrow_forwardFormaldehyde, H2C=O, is known to all biologists because of its usefulness as a tissue preservative. When pure, formaldehyde trimerizes to give trioxane, C3H6O3, which, surprisingly enough, has no carbonyl groups. Only one monobromo derivative (C3H5BrO3) of trioxane is possible. Propose a structure for trioxane.arrow_forward
- In an advanced synthetic chemistry experiment, a researcher prepares a compound, ZY-7, by reacting a ketone (C5H10O) with hydroxylamine (NH2OH), followed by heating in the presence of an acid catalyst. The resulting compound, ZY-7, is then treated with a solution of sodium nitrite (NaNO2) and hydrochloric acid (HCl) at low temperature. Identify the class of compound that ZY-7 most likely belongs to after this series of reactions." A) Amide B) Oxime C) Nitro compound D) Diazonium salt E) Ester Don't use chatgpt please provide valuable answerarrow_forwardButylated hydroxytoluene (BHT) is a common preservativeadded to cereals and other dry foods. Its systematic name is 1-hydroxy-2,6-di-tert-butyl-4-methylbenzene (where “tert-butyl”is 1,1-dimethylethyl). Draw the structure of BHT.arrow_forwardCompounds X and Y have the formula C6H12- Both X and Y react with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2-methylpentane. The heat of hydrogenation of X is less than that of Y. X and Y react with HBr to form a mixture of the same bromoalkanes, and they both undergo hydroboration/oxidation to give a mixture of the same alcohols. What is the structure of Y? In cases where there is more than one answer, just draw one. n. n [ ]# ChemDoodleⓇ zaarrow_forward
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