Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 4, Problem 35P
Interpretation Introduction
Interpretation:
The structure, IUPAC name and the reaction to form the given
Concept introduction:
Addition reaction: It is the reaction in which unsaturated bonds are converted into saturated molecules by the addition of molecules.
Hydrogenation of alkenes or
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draw structural formulas for all isomeric alkanes with molecular formula C7H16. Predict which isomer has the lowest boiling point and which has the highest boiling point.
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
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• In cases where there is more than one answer, just draw one.
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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.
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Chapter 4 Solutions
Organic Chemistry
Ch. 4 - Prob. 1PPCh. 4 - Which structure does not represent...Ch. 4 - Prob. 3PPCh. 4 - Draw bond-line formulas for all of the isomers of...Ch. 4 - Prob. 5PPCh. 4 - Draw bond-line formulas and give IUPAC...Ch. 4 - Draw bond-line formulas and give IUPAC...Ch. 4 - Practice Problem 4.8 Give names for the following...Ch. 4 - Prob. 9PPCh. 4 - Prob. 10PP
Ch. 4 - Prob. 11PPCh. 4 - Give the structures and IUPAC names for all the...Ch. 4 - Prob. 13PPCh. 4 - Practice Problem 4.14 Show by a calculation (using...Ch. 4 - Practice Problem 4.15 Write structures for the cis...Ch. 4 - Practice Problem 4.16
(a) Write structural...Ch. 4 - Practice Problem 4.17 Write a conformational...Ch. 4 - Practice Problem 4.18
(a) Write the two...Ch. 4 - Prob. 19PPCh. 4 - Practice Problem 4.20 (a) What is the index of...Ch. 4 - Practice Problem 4.21
Zingiberene, a fragrant...Ch. 4 - Practice Problem 4.22 Carbonyl groups also count...Ch. 4 - Prob. 23PCh. 4 - Give systematic IUPAC names for each of the...Ch. 4 - Prob. 25PCh. 4 - Write the structure and give the IUPAC systema.tic...Ch. 4 - 4.27. Write the structure(s) of the simplest...Ch. 4 - Prob. 28PCh. 4 - 4.29. Write structures for the following...Ch. 4 - Prob. 30PCh. 4 - A spiro ring junction is one where two rings that...Ch. 4 - 4.32. Tell what is meant by a homologous series...Ch. 4 - Four different cycloalkenes will all yield...Ch. 4 - 4.34. (a) Three different alkenes yield...Ch. 4 - Prob. 35PCh. 4 - Prob. 36PCh. 4 - 4.37. Write the structures of two chair...Ch. 4 - Prob. 38PCh. 4 - Without referring to tables, decide which member...Ch. 4 - Prob. 40PCh. 4 - 4.41. Which compound would you expect to be the...Ch. 4 - Prob. 42PCh. 4 - 4.43. Write the two chair conformations of each of...Ch. 4 - Provide an explanation for the surprising fact...Ch. 4 - Prob. 45PCh. 4 - 4.46. Specify the missing compounds and/or...Ch. 4 - Consider the cis and trans isomers of...Ch. 4 - Prob. 48PCh. 4 - Open the energy-minimized 3D Molecular Models on...Ch. 4 - 4.50. Open the 3D Molecular Models on the book’s...Ch. 4 - 4.51. Open the 3D Molecular Model on the book’s...Ch. 4 - 1. The predominant conformation for D-glucose is...Ch. 4 - Prob. 2LGPCh. 4 - When 1,2-dimethylcyclohexene is allowed to react...Ch. 4 - Prob. 4LGP
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- Alkenes can be converted to alcohols by reaction with mercuric acetate to form a β-hydroxyalkylmercury(II) acetate compound, a reaction called oxymercuration. Subsequent reduction with NaBH4 reduces the C–Hg bond to a C–H bond, forming the alkyl alcohol, a reaction called demercuration. Draw the structures of the Hg-containing compound(s) and the final alcohol product(s) formed in the following reaction sequence, omitting byproducts. If applicable, draw hydrogen at a chirality center and indicate stereochemistry via wedge-and-dash bonds.arrow_forwardAlkenes can be converted to alcohols by reaction with mercuric acetate to form a β-hydroxyalkylmercury(II) acetate compound, a reaction called oxymercuration. Subsequent reduction with NaBH4 reduces the C–Hg bond to a C–H bond, forming the alkyl alcohol, a reaction called demercuration. Draw the structures of the Hg-containing compound(s) and the final alcohol product(s) formed in the following reaction sequence, omitting byproducts. If applicable, draw hydrogen at a chirality center and indicate stereochemistry via wedge-and-dash bonds.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_forward
- explain structural isomerism in aliphatic alkanes and geometric isomerism in alkenes. Describe structural isomerism and the different types that exist. With the aid of diagrams use the molecular formulae C5H12 and C5H10 to explain structural isomerism in aliphatic alkanes and alkenes. Describe geometric isomerism. With the aid of diagrams use the molecular formula C5H10 to explain geometric isomerism in alkenes.arrow_forwardConsider the following reactions: When C5H12 is reacted with Cl2(g) in the presence of ultraviolet light, four different monochlorination products form. What is the structure of C5H12 in this reaction? When C4H8 is reacted with H2O, a tertiary alcohol is produced as the major product. What is the structure of C4H8 in this reaction? When C7H12 is reacted with HCl, 1-chloro-1-methylcyclohexane is produced as the major product. What are the two possible structures for C7H12 in this reaction? When a hydrocarbon is reacted with water and the major product of this reaction is then oxidized, acetone (2-propanone) is produced. What is the structure of the hydrocarbon in this reaction? When C5H12O is oxidized, a carboxylic acid is produced. What are the possible structures for C5H12O in this reaction?arrow_forwardCompounds 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. 1998) 0▾ + n [F ChemDoodle aarrow_forward
- 8 5 Alkenes are unsaturated hydrocarbons. They show structural isomerism. Alkenes take part in addition reactions and form polymers. (a) Structural isomers have the same molecular formula but different structural formulae. Give an example of structural isomerism. molecular formula . two structural formulae (b) Ethene reacts with each of the following. Give the name and structural formula of each product. (i) steam name of product structure of product (ii) hydrogen name of product structure of productarrow_forwardCompound 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_forwardWrite the balanced chemical equation for the complete combustion of ethane. Reactants Products C2H6 (g) + → Formulate (skeletal formula) the main products for the oxidation and dehydration reactions of the following compound: Reactant Oxidation product Dehydration products | OH CH3―CH2―CH―CH2―CH3arrow_forward
- Name and draw structural formulas for all alkenes with the molecular formula C5H10. As you draw these alkenes, remember that cis and trans isomers are different compounds and must be counted separatelyarrow_forwardWhat is the structure of a compound with the formula C7H14O that has an ether and cyclobutane ring, including its IUPAC name? In addition, what is the structure of the compound with the formula C7H14O that does NOT contain the functional groups: epoxide, ether, cycloalkane, alcohol, alkene. Indicate the functional groups used that are present in the structure made for this compound.arrow_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
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