Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 4, Problem 31P
A spiro ring junction is one where two rings that share no bonds originate from a single carbon atom.
(a) For the case of bicyclic spiranes of formula
(b) Write structures for other bicyclic molecules that fit this formula.
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This question is about the chemistry of alkenes, which are unsaturated hydrocarbons.
(a) State what is meant by the term unsaturated as applied to a hydrocarbon.
(1)
(b) An organic compound, X, is an unsaturated hydrocarbon with molecular formula
CH₂.
(i) Draw the displayed formulae and give the names of two molecules with
molecular formula C₂H, which are E/Z isomers.
(3)
Isomer 1
Isomer 2
Name:
Name:
TRUE OR FALSE
(a) Both ethylene and acetylene are planar molecules.
(b) An alkene in which each carbon of the double bond has two different groups bonded to it will show cis-trans isomerism.
(c) Cis-trans isomers have the same molecular formula but a different connectivity of their atoms.
(d) Cis-2-butene and trans -2-butene can be interconverted by rotation about the carbon–carbon double bond.
(e) Cis-trans isomerism is possible only among appropriately substituted alkenes.
(f) Both 2-hexene and 3-hexene can exist as pairs of cis-trans isomers.
(g) Cyclohexene can exist as a pair of cis-trans isomers.
(h) 1-Chloropropene can exist as a pair of cis-trans isomers.
A certain hydrocarbon has a molecular formula of C5H8. Which of the following is not a structural possibility for this hydrocarbon? (a) It is a cycloalkane. (b) It contains one ring and one double bond. (c) It contains two double bonds and no rings. (d) It is an alkyne.
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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- Distinguish between isomerism and resonance. Distinguish between structural and geometric isomerism. When writing the various structural isomers, the most difficult task is identifying which are different isomers and which are identical to a previously written structurethat is, which are compounds that differ only by the rotation of a carbon single bond. How do you distinguish between structural isomers and those that are identical? Alkenes and cycloalkanes are structural isomers of each other. Give an example of each using C4H8. Another common feature of alkenes and cycloalkanes is that both have restricted rotation about one or more bonds in the compound, so both can exhibit cis- trans isomerism. What is required for an alkene or cycloalkane to exhibit cis-trans isomerism? Explain the difference between cis and trans isomers. Alcohols and ethers are structural isomers of each other, as are aldehydes and ketones. Give an example of each to illustrate. Which functional group in Table 21-4 can be structural isomers of carboxylic acids? What is optical isomerism? What do you look for to determine whether an organic compound exhibits optical isomerism? 1-Bromo-1-chloroethane is optically active whereas 1-bromo-2-chloroethane is not optically active. Explain.arrow_forwardDraw the structure(s) of all of the branched alkene isomers, C6H12, that contain 2 methyl branches.arrow_forwardFor the following, you must draw an appropriate structure that has the chemical formula C5H7O2Cl with the indicated functional group(s) and/or property. In each case, identify any other functional groups in the molecule you draw, that were not indicated in the question. You may use Lewis or bond- line structures to draw your molecules. You may not use the same structure to answer more than 1 question. a) An acyclic molecule that cannot form hydrogen bonds with itself b) A tertiary chloride c) A cyclic etherarrow_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_forward(1) Write a complete chemical equation showing reactants, products, and catalysts needed (if any) for the following reaction and (2) Draw and name the organic compound found in every reaction. (a) Complete hydrogenation of 2-Methylhexa-1,5-diene (b) Complete halogenation (Br2) of 3-Ethyl-2,2-dimethylhept-3-ene (c) Reaction of (4E)-2.4-Dimethylhexa-1,4-diene with a mole of water (d) Reaction of cis-3,3-Dimethyl-4-propylocta-1,5-diene with two mole of HBr (e) Reaction of trans-1-Bromo-3-chlorocyclopentane with potassium hydroxide (f) Formation of Gilman reagent using isopropyl bromide (g) Ozonolysis of 3,3-Dimethyloct-4-yne (h) Complete halogenation (Cl2) of 3-Ethyl-5-methyl-1,6,8-decatriyne (i) Partial hydrogenation using Lindlar's Catalyst 2,2,5,5-Tetramethylhex-3-yne (i) Reaction of 3.4-Dimethylcyclodecyne with sodium amidearrow_forwardExcluding compounds that contain substituents on the rings, draw structures for the following bicyclic isomers of C6H10. One spiro alkane with the formula C6H10. One bridged alkane with the formula C6H10.arrow_forward
- 21.) Calculate the enthalpy of hydrogenation of benzene to cyclohexane from the following reactions A,H (kJ/mol) C6H6 (1) + 15/2 02 (g) → 6 CO2 (g) + 3 H20 (1) C6H12 (1) + 9 02 (g) → 6 CO2 (g) + 6 H20 (1) H2 (g) + ½ 02 (g) → H2O (1) -3268 -3920 -285.83 a.) -205 kJ/mol b.) -1507 kJ/mol c.) -938 kJ/mol d.) -366 kJ/molarrow_forwarda) True or false: Alkenes undergo addition reactions andaromatic hydrocarbons undergo substitution reactions.(b) Using condensed structural formulas, write the balancedequation for the reaction of 2-pentene with Br2and name the resulting compound. Is this an addition ora substitution reaction? (c) Write a balanced chemicalequation for the reaction of Cl2 with benzene to make paradichlorobenzenein the presence of FeCl3 as a catalyst. Isthis an addition or a substitution reaction?arrow_forward1. (a) Draw the structures of the eight isomeric pentyl alcohols, C3H11OH. (b) Name each by the IUPAC system and by the carbinol system. (c) Label each as primary, secondary, or tertiary, (d) Which one is isopentyl alcohol? tert-Pentyl alcohol? (e) Give the structure of a primary, a secondary, and a tertiary alcohol of the formula C,H13OH.arrow_forward
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