Interpretation:
Looking at the possible catrbocation intermediates produced during the addition of HCl to 1,3-pentadiene, which adduct 1,2- or 1,4- will be formed as the predominant product is to be stated.
Concept introduction:
Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of bromide ion on each of these forms leads to the formation of a mixture of 1,2- and 1,4-addition products. The more stable form of the allyl cation will yield the major product.
To state:
Which adduct, 1,2- or 1,4-, will be formed as the predominant product during the addition of HCl to 1,3-pentadiene, by looking at the possible catrbocation intermediates in the reaction.
Trending nowThis is a popular solution!
Chapter 14 Solutions
Organic Chemistry
- In light of the fact that tertiary alkyl halides undergo spontaneous dissociation to yield a carbocation plus halide ion (see Problem 10-45), propose a mechanism for the following reaction.arrow_forwardBr Brz CH3 CH3 H3C CH2CI2 H3C Br Electrophilic addition of bromine, Br2; to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl). In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br: :Br: .CH3 H3C H3C CH3 Br:arrow_forward8-) following reactions. Predict the major and minor products of the EtO CH;CH,CHCH, BuO, Brarrow_forward
- Topic: Reactions of benzene Starting from benzene, synthesize the following compounds. Write the complete reagent/s and intermediate product/s. The step by step mechanism (movement of arrow) is not necessary.arrow_forward14-22 In light of your answer to Problem 14-21 propose mechanisms for the reactions below. (a) ÇO2CH3 .CO2CH3 Heat + CO2 + `CO2CH3 ČO2CH3 (b) CH3 CH3 N' N. Heat + C=CH + N2 N. N' CH3 CH3arrow_forwardProvide the whole reaction mechanism (generation of electrophile, nucleophile, bond formation, bond breaking and movement of arrows) and the final product of the following reactions:arrow_forward
- Please send me the question in 30 minutes it's very urgent plzarrow_forwardWhen 1 mole of buta-1,3-diene reacts with 1 mole of HBr, both 3-bromobut-1-ene and 1-bromobut-2-ene are formed. Propose a mechanism to account for this mixture of products.arrow_forwardThe following series of reactions will yield 2) CI-CH2-CH2-C6H5 1) CH3CH2SH + N2OH O 2-chloro-4-ethyl-benzenesulfonic acid O CH;CH2-S-CH2CH2C6H5 O ortho-chloro-ethyl-benzene O 1-phenyl-3-chloro-propane O CH3CH2-O-CH2CH2C6H5arrow_forward
- The following flow chart connects three of the reactions we have discussed that involve carbocation intermediates. Each arrow may represent more than one elementary step in a mechanism.Arrows 1 and 2 summarize the conversion of alcohols to alkyl halides, 3 and 4 the dehydrohalogenation of an alkyl halide to an alkene by the E1 mechanism, and 1 and 4 the formation of an alkene by dehydration of an alcohol. The reaction indicated by arrow 5 constitutes a major focus of the next chapter. There we will explore reactions that give overall addition to the double bond by way of carbocation intermediates. One such process converts alkenes to alkyl halides (5 + 2), another converts alkenes to alcohols (5 + 6).What term best describes the relationship between an alkene and a carbocation? A. Isomers B. Resonance contributors C. Alkene is conjugate acid of carbocation D. Alkene is conjugate base of carbocationarrow_forwardsupply mechanisms for the following reactions showing all intermediates, all formal charges, and use arrows to show electron flowarrow_forwardPropose a reasonable mechanism for the reaction, drawing out Lewis structure, using arrows to show electron flow, clearly identifying the bond making/bond breaking steps, and proposing reasonable intermediates for the reaction.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning