Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Question
Chapter 2, Problem 2.71P
Interpretation Introduction
Interpretation:
It is to be explained why alcohols having the same molecular formula differ significantly in their boiling points.
Concept introduction:
As the surface area increases, the boiling point increases due to increased strengths of intermolecular interactions. As the surface area increases, the ability of individual molecules to attract each other increases. Branching in molecules decreases the surface area, thereby decreasing the attractive forces between individual molecules. As a result, the boiling point decreases.
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Following are three alcohols with the molecular formula C4H10O. Their boiling points, from lowest to highest, are 82.3°C, 99.5°C, and 117°C. Which alcohol has which boiling point?
Why does styrene have a higher boiling point, 145 °C, than isopropanol, 83 °C? Explain
your answer by indicating the types and relative strengths of intermolecular forces present
in each compound (see the line structures given below).
HO
styrene
dipole moment = 0.13 D
isopropanol
dipole moment = 1.66 D
Dimethyl ether and ethanol both have the molecular formula C2H6O. Which would you predict have the higher boiling point? Why?
Chapter 2 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
Ch. 2 - Prob. 2.1PCh. 2 - Prob. 2.2PCh. 2 - Prob. 2.3PCh. 2 - Prob. 2.4PCh. 2 - Prob. 2.5PCh. 2 - Prob. 2.6PCh. 2 - Prob. 2.7PCh. 2 - Prob. 2.8PCh. 2 - Prob. 2.9PCh. 2 - Prob. 2.10P
Ch. 2 - Prob. 2.11PCh. 2 - Prob. 2.12PCh. 2 - Prob. 2.13PCh. 2 - Prob. 2.14PCh. 2 - Prob. 2.15PCh. 2 - Prob. 2.16PCh. 2 - Prob. 2.17PCh. 2 - Prob. 2.18PCh. 2 - Prob. 2.19PCh. 2 - Prob. 2.20PCh. 2 - Prob. 2.21PCh. 2 - Prob. 2.22PCh. 2 - Prob. 2.23PCh. 2 - Prob. 2.24PCh. 2 - Prob. 2.25PCh. 2 - Prob. 2.26PCh. 2 - Prob. 2.27PCh. 2 - Prob. 2.28PCh. 2 - Prob. 2.29PCh. 2 - Prob. 2.30PCh. 2 - Prob. 2.31PCh. 2 - Prob. 2.32PCh. 2 - Prob. 2.33PCh. 2 - Prob. 2.34PCh. 2 - Prob. 2.35PCh. 2 - Prob. 2.36PCh. 2 - Prob. 2.37PCh. 2 - Prob. 2.38PCh. 2 - Prob. 2.39PCh. 2 - Prob. 2.40PCh. 2 - Prob. 2.41PCh. 2 - Prob. 2.42PCh. 2 - Prob. 2.43PCh. 2 - Prob. 2.44PCh. 2 - Prob. 2.45PCh. 2 - Prob. 2.46PCh. 2 - Prob. 2.47PCh. 2 - Prob. 2.48PCh. 2 - Prob. 2.49PCh. 2 - Prob. 2.50PCh. 2 - Prob. 2.51PCh. 2 - Prob. 2.52PCh. 2 - Prob. 2.53PCh. 2 - Prob. 2.54PCh. 2 - Prob. 2.55PCh. 2 - Prob. 2.56PCh. 2 - Prob. 2.57PCh. 2 - Prob. 2.58PCh. 2 - Prob. 2.59PCh. 2 - Prob. 2.60PCh. 2 - Prob. 2.61PCh. 2 - Prob. 2.62PCh. 2 - Prob. 2.63PCh. 2 - Prob. 2.64PCh. 2 - Prob. 2.65PCh. 2 - Prob. 2.66PCh. 2 - Prob. 2.67PCh. 2 - Prob. 2.68PCh. 2 - Prob. 2.69PCh. 2 - Prob. 2.70PCh. 2 - Prob. 2.71PCh. 2 - Prob. 2.72PCh. 2 - Prob. 2.1YTCh. 2 - Prob. 2.2YTCh. 2 - Prob. 2.3YTCh. 2 - Prob. 2.4YTCh. 2 - Prob. 2.5YTCh. 2 - Prob. 2.6YTCh. 2 - Prob. 2.7YTCh. 2 - Prob. 2.8YTCh. 2 - Prob. 2.9YTCh. 2 - Prob. 2.10YTCh. 2 - Prob. 2.11YTCh. 2 - Prob. 2.12YTCh. 2 - Prob. 2.13YTCh. 2 - Prob. 2.14YTCh. 2 - Prob. 2.15YTCh. 2 - Prob. 2.16YTCh. 2 - Prob. 2.17YTCh. 2 - Prob. 2.18YTCh. 2 - Prob. 2.19YTCh. 2 - Prob. 2.20YT
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Similar questions
- Arrange these compounds in order of increasing boiling point (values in C are 42, 24, 78, and 118). (a) CH3CH2OH (b) CH3OCH3 (c) CH3CH2CH3 (d) CH3COOHarrow_forwardDraw Lewis structures and condensed structural formulas for the four alcohols with the molecular formula C4H10O. Classify each alcohol as primary, secondary, or tertiary. (Hint: First consider the connectivity of the four carbon atoms; they can be bonded either four in a chain or three in a chain with the fourth carbon as a branch on the middle carbon. Then consider the points at which the iOH group can be bonded to each carbon chain.)arrow_forwardThe boiling points of aldehydes and ketones is higher than that of alkanes but lower than that of alcohols. O True Falsearrow_forward
- Order the following hydrocarbons from lowest to highest boiling point: C2H6, C3H8, and C4H10.arrow_forwardthanol (CH3CH2OH) and dimethyl ether (CH3OCH3) are constitutional isomers. Q) Predict which of the two has the higher boiling pointarrow_forwardAll of the following alcohols have the same molecular formula (C5H120), but they have significantly different boiling points. Explain why. OH НО ОН 2-Methylbutan-2-ol Boiling point = 102 °C Pentan-1-ol Pentan-3-ol Boiling point = 136–138 °C Boiling point = 114–115 °Carrow_forward
- 分 Arrange the following compounds in order of decreasing boiling point (highest to lowest) Highest boiling point 1 | CH3CH2COOH ! CH3(CH2)2CH3 3 ! CH3(CH2)2OH 4 ! CH3C(CH3)2CH3 | CH3CH2CH3 Lowest Boiling pointarrow_forwardEthanol and dimethyl ether have the same molecular formula C2H6O. Ethanol is liquid at room teperature while dimethyl ether is gas. How is this possible? Explain.arrow_forwardWhich one of the following two compounds has the stronger IMF - and therefore the higher boiling point? Ne He Which one of the following two compounds has the stronger IMF - and therefore the higher boiling point? Cl2 MgS Which one of the following two compounds has the stronger IMF - and therefore the higher boiling point? NH3 methanearrow_forward
- 12. Write bond-line structural formulas for (a.) two primary alcohols, (b.) a secondary alcohol, and (c.) a tertiary alcohol-all having the molecular formula CaH100.arrow_forwardSelect the compound with the highest boiling point. I CH3CH2CH½CH2NH2 II CH3CH;NHCH,CH3 III CH3CH;NCH3 CH3arrow_forwardShow that the addition of each CH2 unit to an alcohol molecule changes the heat of combustion by: 2(C-H)+1(C-C)+1.5(O=O) – [2(C=O)+2(O-H)]arrow_forward
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