EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
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The diagram shows the skeletal formula of cyclobutane.
The enthalpy change of formation of cyclobutane is +75.1 kJ mol-1. and the enthalpy
change of atomisation of graphite is +712 kJ mol-1.
The bond enthalpy of C-H is 390 kJ mol-1 and of H-H is 429 kJ mol-1.
What is the average bond enthalpy of the C-C bond in cyclobutane, rounded to the
nearest whole number?
A 236 kJ mol-
B 315 kJ mol-
C 342 kJ mol-
D
D 700 kJ mol-
5. Acetone and 2-propanol are chemically interconvertible. Reduction (by the addition of the equivalent of H2) of acetone yields 2-propanol. Conversely, oxidation (by the removal of the equivalent of H2) of 2-propanol yields acetone.
Is the evaporation data for these substances the same or different? If different, can you account for why this may be the case from a comparison of the Lewis structures of each substance and the IMFs present in each substance? Explain.
Structural Isomers: Alkanes
One of the reasons for the complexity of carbon compounds is that it can bond (catenate) with itself. Oils are mostly made up of hydrocarbons, for 'saturated' compounds, these obey the formula CnH2n+2. The empirical formula (unlike benzene) will vary with n. Now we have established C is tetrahedral, how many structural (skeletal) isomers can we find for n=6, hexane C6H14 ?
1) Sketch all the isomers. What procedure did you use to make sure you didn’t miss any ? Do you think you could you do this now for heptane C7H16 ?! (Hint: 9 different ‘skeletal’ topologies)
Note the number of possible isomers increases in highly exponential way. C10 – 75 isomers C15 – 4,347 isomers C20 - 366,319 isomers !!
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