Concept explainers
Interpretation:
The chain reaction mechanism for the formation of
Concept introduction:
Radical halogenation is the reaction in which hydrogen atoms of
At normal temperature and pressure, chlorine and methane do not react with each other. The reaction is initiated by light or heat. When exposed to light,
The reaction that is initiated by light is more efficient because a very small amount of light photons allows a large number of products to be formed.
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Organic Chemistry
- Ethane reacts with chlorine (Cl2) in the presence of ultra-violet (UV) light, to produce 1-chloropropane (CH3CH2Cl) and hydrogen bromide (HCl). As shown in the equation below.CH3CH3+ Cl2→ CH3CH2Cl+ HClDescribe the reaction mechanism of the reaction between ethane and chlorine to produce 1-chloroethane. The description should be detailed and must include the type of bond fission that takes place. You may sketch and insert suitable diagrams to aid your description if you wish.arrow_forwardConcentrated phosphoric acid and concentrated sulfuric acid are common choices for dehydrating alcohols. Concentrated hydrochloric acid is not. What problem might occur if concentrated hydrochloric acid were substituted for phosphoric acid in the cyclohexene synthesis? allylic chlorination of the cyclohexene product may occur chlorocyclohexane may form as a byproduct the equilibrium will now favor formation of cyclohexanol by Le Chatelier's Principle hydrochloric acid is a weaker acid than phosphoric acidarrow_forwardFree‑radical halogenation can occur with chlorine and a source of direct UV radiation or sunlight. Chlorination of 2,4‑dimethylpentane via radical halogenation leads to the formation of all three of the products shown. Estimate the relative percentages of each product that will be formed using this means of halogenation. Presume that 1 equivalent of chlorine is used.arrow_forward
- Elimination of HBr from 2-bromobutane affords a mixture of 1-butene and 2-butene. With sodium ethoxide as base, 2-butene constitutes 81% of the alkene products, but with potassium tert-butoxide, 2-butene constitutes only 67% of the alkene products. Offer an explanation for this difference.arrow_forwardDraw the mechanism for the conversion of propanedial (see Problem 7.43) in its keto form to its enol form under basic and acidic conditions. Do the same for the conversion from the enol form to the keto form.arrow_forwardWhen 2-bromo-2-methylbutane is treated with a base, a mixture of 2-methyl-2-butene and 2-methyl-1- butene is produced. When potassium hydroxide is the base, 2-methyl-1-butene accounts for 45% of the product mixture. However, when potassium tert-butoxide is the base, 2-methyl-1-butene accounts for 70% of the product mixture. What percent of 2-methyl-1-butene would be in the mixture if potassium propoxide were the base? base Br A. Less than 45% B. C. 45% Between 45% and 70% D. More than 70%arrow_forward
- The relative rates of reaction of ethane, toluene, and ethylbenzene with bromine atoms have been measured. The most reactive hydrocarbon undergoes hydrogen atom abstraction a million times faster than does the least reactive one. Arrange these hydrocarbons order of decreasing reactivity.arrow_forwardThe high reactivity of alkyl halides can be explained in terms of nature of C-X bond which is highly polarized covalent bond due to large difference in the electronegativities of carbon and halogen atom. This polarity is responsible for the nucleophilic substitution reactions of alkyl halides which mostly occur by Swa and Swa mechanisms. Sy reaction is a two-step process and in the first step, R-X ionizes to give carbocation (slow process). In the second step, the nucleophile attacks the carbocation from either side to form the product (fast process). In Swi reaction, there can be racemization and inversion. Swi reaction is favored by heavy (bulky) groups on the carbon atom attached to halogens. i.e., R,C-X>R;CH-X>R-CH,X>CH,X. In Sna reaction, the strong nucleophile OH attacks from the opposite side of the chlorine atom to give an intermediate (transition state) which breaks to yield the product (alcohol) and leaving (X) group. The alcohol has a configuration opposite to that of the…arrow_forwardSelect the correct isomer of 2-bromo-4-isopropyl-1-methylcyclohexane that, when subjected to ethoxide followed by hydrogenation, would yield a single isomer of 4-isopropyl-1- methylcyclohexane.arrow_forward
- Optically pure Compound 1 undergoes a reaction at room temperature with sodium methoxide (NaOCH3) in methanol to form a single isomer of Compound 2 as shown below: 3. The rate of the above reaction is determined experimentally to follow second-order kinetics. Give a fully labelled sketch of a reaction coordinate diagram for the reaction. 4. draw a mechanism on a piece of paper (using curly arrows) to show the formation of Compound 2 from Compound 1 including any activated complex.arrow_forwardAccount for the fact that the bicyclic ether (3) is formed from the trans isomer but not from the cis isomer.arrow_forwardWhich of the following molecules are likely to undergo a 1,2 alkyl shift during acid-catalyzed hydration? Mark all that apply. 2,3-dimethyl-1-butene 3,3-dimethyl-1-butene 2-methyl-1-butene 3-methyl-1-butenearrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning