Concept explainers
Interpretation:
The monochloride products of photochemical chlorination of heptane other than
Concept Introduction:
>The relative rates of replacement of different types of hydrogen atoms by a halogen in an
The product distribution depends on the relative rates and the number of equivalent sites of each type.
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- A chemist wanted to determine experimentally the relative ease of removing a hydrogen atom from a tertiary, a secondary, and a primary carbon by a chlorine radical. He allowed 2-methylbutane to undergo chlorination at 300 °C and obtained as products 36% 1-chloro-2-methylbutane, 18% 2-chloro-2-methylbutane, 28% 2-chloro-3-methylbutane, and 18% 1-chloro-3-methylbutane. What values did he obtain for the relative ease of removing a hydrogen atom from tertiary, secondary, and primary hydrogen carbons by a chlorine radical under the conditions of his experiment?arrow_forwardPhotochemical chlorination of 2,2,4-trimethylpentane gives four isomeric monochlorides. (a) Write structural formulas for these four isomers. (b) The two primary chlorides make up 65% of the monochloride fraction. Assuming that all the primary hydrogens in 2,2,4-trimethylpentane are equally reactive, estimate the percentage of each of the two primary chlorides in the product mixture.arrow_forwardWrite a pair of chain propagation steps for the radical bromination of propane to give 1-bromopropane. Then calculate ▲H° for each propagation step and for the overall reaction.arrow_forward
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- 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.arrow_forwardThe reaction of DBU with 2-bromoheptane gives two alkene products, what are they? Which of these would you expect to be the major product? Explain your answer.arrow_forwardA saturated hydrocarbon burns in oxygen to give carbon dioxide and water. Approximately twice as much CO2 as H2O (by weight) is produced by this combustion, the actual factor being 2.03. Light induced chlorination of the hydrocarbon by 2.0 equivalents of chlorine gives a mixture of mono-, di- and trichloro compounds, along with small amounts of higher chlorination products. Only one monochloro isomer is formed, but there are two dichloro isomers and three trichloro isomers produced in the reaction. Based on this information, you should be able to identify the hydrocarbon, and draw structural formulas for the chlorinated compounds.arrow_forward
- Does the data provide evidence for the claim that the reaction of Br2 with alkenes proceeds via anti‐addition? The mleting point of the product was found to be 234.5-235.5C chemical reaction: trans-stilbene+pyrimindine tribromide --->acetic acid 1,2-di bromo-1,2-diphenylethanearrow_forwardFree radical halogenation is used to replace one or more hydrogens on an alkane with one or more halogens (either chlorine or bromine). It is a substitution reaction. A student performs a free radical bromination on 3-methyl-pentane (5.88 g) to create the desired product of 3-bromo-3-methyl-pentane. The product mix, which hopefully contains almost all 3-bromo-3-methyl-pentane, is cleaned up by passing it through a gas chromoatograph, which separates out the 3-bromo-3-methyl-pentane from any undesired products made during the reaction (undesired products are created frequently in free radical halogenation). The initial product mix weighed 9.45 g; the purified 3-bromo-3-methyl-pentane weighed 7.21 g. What is the student's percent recovery?arrow_forwardWhy does deuterium add to C-1 rather than to C-4 in the preceding reaction? a. Why was DCl rather than HCl used in the reactionarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningMacroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks Cole