Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Textbook Question
Chapter 2.7, Problem 2.15P
Arrange the
- (a) 2-Methylbutane, 2,2-dimethylpropane, and pentane
- (b) 3,3-Dimethylheptane, 2,2,4-trimethylhexane, and nonane
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Chapter 2 Solutions
Organic Chemistry
Ch. 2.2 - Do the line-angle formulas in each pair represent...Ch. 2.2 - Draw line-angle formulas for the three...Ch. 2.3 - Write IUPAC names for these alkanes.Ch. 2.4 - Combine the proper prefix, infix, and suffix and...Ch. 2.4 - Write the molecular formula, IUPAC name, and...Ch. 2.4 - Write molecular formulas for each bicycloalkane,...Ch. 2.4 - Prob. 2.7PCh. 2.5 - For 1,2-dichloroethane: (a) Draw Newman...Ch. 2.5 - Following is a chair conformation of cyclohexane...Ch. 2.5 - Draw the alternative chair conformation for the...
Ch. 2.5 - Draw a chair conformation of...Ch. 2.6 - Which cycloalkanes show cis, trans isomerism? For...Ch. 2.6 - Following is a planar hexagon representation for...Ch. 2.6 - Here is one cis,trans isomer of...Ch. 2.6 - Prob. AQCh. 2.6 - Prob. BQCh. 2.6 - Prob. CQCh. 2.7 - Arrange the alkanes in each set in order of...Ch. 2 - Write a line-angle formula for each condensed...Ch. 2 - Write the molecular formula of each alkane.Ch. 2 - Using parentheses and subscripts, provide an even...Ch. 2 - Which statements are true about constitutional...Ch. 2 - Prob. 2.20PCh. 2 - Each member of the following set of compounds is...Ch. 2 - Each of the following compounds is an amine...Ch. 2 - Each of the following compounds is either an...Ch. 2 - Draw structural formulas and write IUPAC names for...Ch. 2 - Draw structural formulas for all of the following....Ch. 2 - Write IUPAC names for these alkanes and...Ch. 2 - Write structural formulas and line-angle formulas...Ch. 2 - Explain why each is an incorrect IUPAC name and...Ch. 2 - For each IUPAC name, draw the corresponding...Ch. 2 - Write the IUPAC name for each compound.Ch. 2 - Prob. 2.31PCh. 2 - Torsional strain resulting from eclipsed CH bonds...Ch. 2 - How many different staggered conformations are...Ch. 2 - Consider 1-bromopropane, CH3CH2CH2Br. (a) Draw a...Ch. 2 - Consider 1-bromo-2-methylpropane and draw the...Ch. 2 - trans-1,4-Di-tert-butylcyclohexane exists in a...Ch. 2 - From studies of the dipole moment of...Ch. 2 - Prob. 2.38PCh. 2 - Following are the alternative chair conformations...Ch. 2 - Prob. 2.40PCh. 2 - Prob. 2.41PCh. 2 - Draw line-angle formulas for the cis and trans...Ch. 2 - Name and draw structural formulas for all...Ch. 2 - Using a planar pentagon representation for the...Ch. 2 - Gibbs free energy differences between...Ch. 2 - Prob. 2.46PCh. 2 - Calculate the difference in Gibbs free energy in...Ch. 2 - Draw the alternative chair conformations for the...Ch. 2 - Use your answers from Problem 2.48 to complete the...Ch. 2 - There are four cis,trans isomers of...Ch. 2 - Draw alternative chair conformations for each...Ch. 2 - 1,2,3,4,5,6-Hexachlorocyclohexane shows cis,trans...Ch. 2 - Prob. 2.53PCh. 2 - What generalization can you make about the...Ch. 2 - What unbranched alkane has about the same boiling...Ch. 2 - Complete and balance the following combustion...Ch. 2 - Following are heats of combustion per mole for...Ch. 2 - Following are structural formulas and heats of...Ch. 2 - Without consulting tables, arrange these compounds...Ch. 2 - Which would you predict to have the larger (more...Ch. 2 - Following are structural formulas for 1,4-dioxane...Ch. 2 - Following is a planar hexagon representation of...Ch. 2 - On the left is a stereorepresentation of glucose...Ch. 2 - Prob. 2.64PCh. 2 - Prob. 2.65P
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- Give the molecular, structural and displayed formulae of the following molecules: (a) 2,2-dimethylpropane (b) 3-bromo-2, 4, 4-trimethyloctanearrow_forwardTRUE 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.arrow_forward3. Identify to which class of compound/functional group each of the following belongs. ( (a) OH CH3-C-CH2CH3 CH3 Class: (b) CI C-CH3 Class:arrow_forward
- 4. Which of the following has a higher boiling point? Explain your answer:(a) 2-propanol or 2-butanol(b) Dimethyl ether or ethanolarrow_forwardGive brief explanation.arrow_forwardWhich of the following substances exist as can cis–trans isomers? Draw both isomers for those that do.(a) 2,3-Dimethylpent-2-ene (condensed structures only)(b) 2-Methylhex-2-ene (both condensed and line structures)(c) Hex-2-ene (line structures only)arrow_forward
- Draw both condensed and line structures corresponding to the following IUPAC names:(a) 3-Methylhept-1-ene (b) 4,4-Dimethylpent-2-yne(c) 2-Methylhex-3-ene (d) 1,3,3-Trimethylcyclohexenearrow_forwardThe melting points and boiling points of two isomeric alkanes are as follows: CH3(CH2)6CH3, mp = -57 °C and bp = 126 °C; (CH3)3CC(CH3)3, mp = 102 °C and bp = 106 °C. (a) Explain why one isomer has a lower melting point but higher boiling point. (b) Explain why there is a small difference in the boiling points of the two compounds, but a huge difference in their melting points.arrow_forwardIndicate whether each statement is true or false. (a) Alkanesdo not contain any carbon–carbon multiple bonds.(b) Cyclobutane contains a four-membered ring. (c) Alkenescontain carbon–carbon triple bonds. (d) Alkynes containcarbon–carbon double bonds. (e) Pentane is a saturatedhydrocarbon but 1-pentene is an unsaturated hydrocarbon.(f) Cyclohexane is an aromatic hydrocarbon. (g) The methylgroup contains one less hydrogen atom than methane.arrow_forward
- Ethanol (CH3CH2OH) and dimethyl ether (CH3OCH3) are constitutional isomers. (a) Predict which of the two has the higher boiling point. (b) Predict which of the two is more soluble in water.arrow_forwardGive the correct IUPAC name for the compound with the following structural formula. CH3 (a) 2-ethyl-1,4-dimethylcyclopentane (b) 3-ethyl-1,4-dimethylcyclohexane (c) 1-ethyl-2,5-dimethylcyclohexane (d) 2-ethyl-1,4-dimethylcyclohexane (e) cyclic-2-ethyl-1,4-dimethylhexane CH2CH3 CH3 a b d earrow_forward2.24 The general molecular formula for alkanes is C„H2n+2. What is the general molecular formula for: (a) Cycloalkanes (b) Alkenes (c) Alkynes (d) Cyclic hydrocarbons that contain one double bondarrow_forward
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