Concept explainers
Interpretation:
The mechanism for the given reaction of electrophilic addition of mixed halogen
Concept introduction:
In the halogen molecule, as both atoms are same, any halogen atom acts as an electrophile and gets attacked by the
The electrophilic addition of halogen molecule across the
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ORGANIC CHEM. PRIN AND MECHANISM LL+ AC
- Reaction of this bicycloalkene with bromine in carbon tetrachloride gives a trans dibromide. In both (a) and (b), the bromine atoms are trans to each other. However, only one of these products is formed. Which trans dibromide is formed? How do you account for the fact that it is formed to the exclusion of the other trans dibromide?arrow_forwardTreatment of 1,2-dibromoethane with the dithiolate dianion shown in the reaction below leads to two products as shown. Draw the structure for each molecular formula and provide a detailed mechanism for the formation of both products.arrow_forwardProvide the major product expected for the following reactions. Omit byproducts. Ignore stereochemistry. Hint: if more than one product is possible, draw only the one that fits in the context of this two-step scheme.arrow_forward
- Predict the major organic product for the following reaction sequence, and then determine the stereochemical nature of the final product.arrow_forwardb) Explain in detail what characteristics of the alkyl halide influence whether a mechanism will be SN1 or SN2. c) Explain in detail what characteristics of a nucleophile influence whether a reaction will be SN1 or SN2.arrow_forwardStrong support for the mechanism of the nucleophilic aromatic substitutionreaction that proceeds through a benzyne intermediate comes from the reaction shown here, in which bromobenzene is treated with KNH2 in the presence of cyclopentadiene. A product that is isolated has the formula C11H10. Draw the structure of that product and explain how it validates the production of a benzyne intermediate.arrow_forward
- Write down all possible alkene products from the following Elemination reaction (no mechanism is required) indicate which one will be major product. And explain it?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_forwardConsider the reaction scheme shown below. HCI [1] ОН (a) Provide a detailed mechanism for reaction [1].arrow_forward
- For each of the questions below – determine whether the following combinations of reactants, will react by substitution (SN1 or SN2 mechanism), elimination (E1 or E2 mechanism) or will not react under the conditions given. draw the final structure and explain the logic for each decision. There may be multiple possible options for some reactions. You must include all 4 aspects of these reactions, substrate, nucleophile, solvent and leaving group in the decisionarrow_forward1. Consider the following reaction. The reagent for the elimination/substitution reaction contains the following anions: Br and CN". он several products a) Define the reaction conditions for the reaction above. Explain in detail. b) Which of the anions will take part in the reaction? Explain. c) Provide the structures of all major products. Specify the stereochemistry where applicable and state the reaction type leading to each product. d) Provide a reaction mechanism for the formation of the products listed in c.arrow_forwardElectrophilic addition to an alkene proceeds via Markovnikov regiochemistry due to the formation of the more stable carbocation intermediate. In the case of conjugated dienes, that is dienes that are separated by one sigma bond, the carbocation that is formed is stabilized additionally by resonance. Addition of the nucleophile to the carbocation intermediate can therefore give two types of products: direct addition to the double bond, also called 1,2-addition, and conjugate addition to the resonance stabilized carbocation, also called 1,4-addition.Allylic carbocation stability is affected by both the nature of the carbocation (primary allylic, secondary allylic, or tertiary allylic) and by the degree of substitution of the double bond. The latter is typically the dominant effect and so a primary allylic carbocation with a trisubstituted double bond is more stable than a tertiary allylic carbocation with a monosubstituted double bond.Electrophilic addition to a conjugated diene is…arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning