Introduction to General, Organic and Biochemistry
11th Edition
ISBN: 9781285869759
Author: Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher: Cengage Learning
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Chapter 11, Problem 11.32P
11-32 Calculate the actual C-C-C bond angles in planar (a) cyclopropane and (b) cyclopentane and com pare them with optimal bond angles.
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3-35
Each of the following descriptions applies to more than one alkane. In each case, draw and name two structures that match
the description.
(a) an isopropylheptane
(d) a trans-dihalocyclopentane
(b) a diethyldecane
(e) a (2,3-dimethylpentyl)cycloalkane
(c) a cis-diethylcyclohexane
(f) a bicyclononane
Draw an expanded structural formula of pent-1-en-3-yne/ CH3-CC-CH=CH2 and then label each carbon. Indicate the longest and shortest C-H bond and predict the C—C single bond that has the highest BDE(bond dissociation energy).
Are the C¬C bonds cyclopropane weaker than those in cyclohexane?
Chapter 11 Solutions
Introduction to General, Organic and Biochemistry
Ch. 11.2 - Prob. 11.1PCh. 11.3 - Prob. 11.2PCh. 11.3 - Prob. 11.3PCh. 11.4 - Problem 11-4 Write the molecular formula and IUPAC...Ch. 11.6 - Problem 11-5 Write the molecular formula and IUPAC...Ch. 11.7 - Prob. 11.6PCh. 11.8 - Prob. 11.7PCh. 11.9 - Prob. 11.8PCh. 11.10 - Prob. 11.9PCh. 11 - Answer true or false. A hydrocarbon is composed...
Ch. 11 - 11-11 Define: Hydrocarbon Alkane Saturated...Ch. 11 - 11-12 Why is it not accurate to describe an...Ch. 11 - 11-13 What is meant by the term line-angle formula...Ch. 11 - Prob. 11.14PCh. 11 - Write the molecular formula for each alkane.Ch. 11 - Answer true or false. Constitutional isomers have...Ch. 11 - Which statements are true about constitutional...Ch. 11 - Prob. 11.18PCh. 11 - Each member of the following set of compounds is...Ch. 11 - Prob. 11.20PCh. 11 - 11-21 In the six following sets, which pairs of...Ch. 11 - Draw line-angle formulas for the nine...Ch. 11 - Answer true or false. The parent name of an alkane...Ch. 11 - Prob. 11.24PCh. 11 - Among the ingredients listed in one commercial...Ch. 11 - Prob. 11.26PCh. 11 - Answer true or false. Cycloalkanes are saturated...Ch. 11 - Prob. 11.28PCh. 11 - Prob. 11.29PCh. 11 - Prob. 11.30PCh. 11 - Prob. 11.31PCh. 11 - 11-32 Calculate the actual C-C-C bond angles in...Ch. 11 - Prob. 11.33PCh. 11 - 11-34 What structural feature of cycloalkanes...Ch. 11 - Prob. 11.35PCh. 11 - 11-36 Name and draw structural formulas for the...Ch. 11 - Name and draw structural formulas for the six...Ch. 11 - 11-38 Why is equatorial methylcyclohexane more...Ch. 11 - Prob. 11.39PCh. 11 - Consider a cyclohexane ring substituted with one...Ch. 11 - Prob. 11.41PCh. 11 - In Problem 11-22, you drew structural formulas for...Ch. 11 - Which unbranched alkane (Table 11-4) has about the...Ch. 11 - Prob. 11.44PCh. 11 - Prob. 11.45PCh. 11 - Prob. 11.46PCh. 11 - Prob. 11.47PCh. 11 - 11-48 How are the boiling points of hydrocarbons...Ch. 11 - Answer true or false. Combustion of alkanes is an...Ch. 11 - 11-50 Write balanced equations for the combustion...Ch. 11 - The heat of combustion of methane, a component of...Ch. 11 - 11-52 Draw structural formulas for these...Ch. 11 - Prob. 11.53PCh. 11 - 11-54 Complete and balance the equation for the...Ch. 11 - Name and draw structural formulas for all pos...Ch. 11 - Prob. 11.56PCh. 11 - Prob. 11.57PCh. 11 - 11-58 (Chemical Connections 11A) How many rings in...Ch. 11 - Prob. 11.59PCh. 11 - Prob. 11.60PCh. 11 - Prob. 11.61PCh. 11 - 11-62(Chemical Connections 11C) What are Freons?...Ch. 11 - 11-63 (Chemical Connections 11C) In what way do...Ch. 11 - (Chemical Connections 11C) What are HFCs and...Ch. 11 - Prob. 11.65PCh. 11 - Prob. 11.66PCh. 11 - Which of the following compounds can exist as...Ch. 11 - Prob. 11.68PCh. 11 - Dodecane, C12H26, is an unbranched alkane Predict...Ch. 11 - Prob. 11.70PCh. 11 - Prob. 11.71PCh. 11 - Prob. 11.72PCh. 11 - As stated in Section 11-9, the wax found in apple...Ch. 11 - Prob. 11.74P
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- 12-31 Cyclodecene exists as both cis and trans isomers. Draw line-angle formulas for each isomer, showing the configuration of the double bond in each.arrow_forward11-38 Why is equatorial methylcyclohexane more stable than axial methylcyclohexane?arrow_forwardIf you examine the structural formulas for the following cycloalkenes, you will see that the configuration of the double bond is cis in each. Cyclopentene Cyclohexene Cycloheptene All attempts to synthesize these cycloalkenes in which the double bond has a trans configuration have failed. Apparently, it is impossible to have a trans configuration in these cycloalkenes. Offer an explanation for why this is so.arrow_forward
- Dodecane, C12H26, is an unbranched alkane Predict the following: Will it dissolve in water? Will it dissolve in hexane? Will it burn when ignited? Is it a liquid, solid, or gas at room temperature and atmospheric pressure? Is it more or less dense than water?arrow_forward11-13 What is meant by the term line-angle formula as applied to alkanes and cycloalkanes?arrow_forwardFrom the data in Figure 4-12 and Table 4-1, estimate the percentages of molecules that have their substituents in an axial orientation for the following compounds: (a) Isopropylcyclohexane (b) Fluorocyclohexane (c) Cyclohexanecarbonitrile, C6H11CNarrow_forward
- 12-77 Show how to convert cyclopentene into these compounds. 1,2-Dibromocyclopentane Cyclopentanol Iodocyclopentane Cyclopentanearrow_forwardFollowing is the structural formula of hexabromocyclododecane. This compound was at one time used as a flame retardant in polystyrene foam insulation in buildings, but has now been banned because it had been shown to be toxic to aquatic organisms, and can disrupt thyroid hormone levels in laboratory test animals. In addition, it persists in the environment. Show how this flame retardant could be synthesized from a cycloalkatriene and write the structural formula and IUPAC name of this starting material. Br Hexabromocyclododecanearrow_forwardDraw structural formulas for all possible carbocations formed by the reaction of each alkene with HC1. Label each carbocation as primary, secondary, or tertiary. ch3 I ch3ch,c=chch3 ch3ch2ch=chch3arrow_forward
- 11-34 What structural feature of cycloalkanes makes cis- trans isomerism in them possible?arrow_forwardEstimate the heat released when ethene(CH2=CH2) reacts with HBr to giveCH3CH2Br. Bond enthalpies areC-H : 412 kJ/mol; C-C : 348 kJ/mol;C=C : 612 kJ/mol; C-Br : 276 kJ/mol;Br-Br : 193 kJ/mol; H-Br : 366 kJ/mol. Choose the correct answer:1. 1036 kJ/mol2. 58 kJ/mol3. 424 kJ/mol4. 200 kJ/mol5. 470 kJ/molarrow_forwardDraw the skeletal (line-bond) structure of (1R,2S)-1-bromo-2-methylcyclohexanearrow_forward
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