Interpretation:
The mechanism of the given reaction between 1,4-pentadiene and N- bromosuccinimide (NBS), initiated by photochemical energy is to be proposed.
Concept introduction:
舧 Electrophiles are electron-deficient species, which has positive or partially positive charge. Lewis acids are electrophiles, which accept electron pair.
舧 Nucleophiles are electron-rich species, which has negative or partially negative charge. Lewis bases are nucleophiles, which donate electron pair.
舧 Free radical is an atom, molecule or ion that has an unpaired electron, which makes it highly chemically reactive.
舧 Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.
舧 Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.
舧 Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.
舧 The reaction in which there is addition of hydrogen molecule is called hydrogenation reaction.
舧
舧 Hydrogenation with platinum as a catalyst is used to convert unsaturated carbohydrates to saturated hydrocarbons
舧 Oxidation of
舧 Ozonolysis helps convert the carbon – carbon double bonds to carbon – oxygen double bond (carbonyl compounds).
舧 Dimethyl sulfide is used as a reducing agent that decomposes the intermediate formed into the carbonyl group.
舧 NBS (nitro-bromo succinimide) is a special reagent used for bromination of allylic carbocations.
舧 Bromine replaces the hydrogen attached to the carbon adjacent to the carbon bearing double bond.
舧 This method of using NBS can produce allylic bromides without bromine reacting with the double bond.
舧 Dehydration of a primary alcohol in the presence of a mineral acid like concentrated sulfuric acid results in the formation of alkene via E2 elimination.
舧 Allylic bromination is the replacement of the hydrogen bonded to the carbon adjacent to the carbon bearing double bond. N-bromosuccinimide is the reagent that can replace bromine gas, since bromine can replace the double bonds.
舧 Electrophilic addition reactions of alkadienes result in formation of products with different stereoisomers.
Want to see the full answer?
Check out a sample textbook solutionChapter 13 Solutions
Organic Chemistry
- predict the product of the following reaction and write the mechanismarrow_forwardGive a detailed reaction mechanism for the reaction expected to occur when 2-bromo-2-methylpentane is heated with sodium methoxide. Draw clear structural formulas of all relevant species and use curved arrows to represent electron flow. Discuss the stability of the final compoundarrow_forwardShow how free-radical halogenation might be used to synthesize the followingcompounds. In each case, explain why we expect to get a single major product.(a) 1-chloro-2,2-dimethylpropane (neopentyl chloride)arrow_forward
- provide a mechanism that explains the formation of the major product of the reaction. Please use resonance structures to explain the regiochemistry of this reaction and provide a detailed mechanism of this reaction.arrow_forwardConsider the reaction shown below. Provide a complete arrow-pushing mechanism that accounts for the formation of the product.arrow_forwardProvide the final product and mechanism for the following reactionsarrow_forward
- Consider the following statement in reference to SN1, SN2, E1, and E2 reactions of haloalkanes. To which mechanism(s), if any, does the statement apply? Involves a carbocation intermediatearrow_forwardWrite arrow-pushing mechanisms for the following reaction. Make sure that your mechanisms explain the observed stereochemistry of the transformations, if relevant.arrow_forwardShow the mechanism and give the products for the following reaction. Pay attention to regio/stereo-chemistry.arrow_forward
- Give the product and mechanism for the following intramolecular reaction. Be sure to include all mechanism arrows, lone pairs, and formal charges. The product is an ether.arrow_forwardSuggest a mechanism for reactions 1,2,3,4 of the following series of reactionsarrow_forwardProvide the necessary sequence of reactions to generate the products below from their respective starting materials.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning