Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 14.3, Problem 5P
Interpretation Introduction
Interpretation:
A mechanism for the inter-conversion of 1,2 adduct and 1,4 adduct formed by the reaction of HBr with 1,3-butadiene which are in equilibrium at 40°C is to be proposed.
Concept introduction:
The mechanism of the interconversion required takes place through i) ionization of the halide to yield an allyl carbocation b) resonance delocalization to yield a different allyl carbocation c) attack of bromide ion on both carbocations.
To propose:
A mechanism for the inter-conversion of 1,2 adduct and 1,4 adduct formed by the reaction of HBr with 1,3-butadiene which are in equilibrium at 40°C.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Addition of one mole of HCl to isoprene gives 4-chloro-2-methyl-2-butene as the major product. Propose a mechanism for this addition and account for its regioselectivity.
Acid-catalyzed dehydration of neopentyl alcohol, (CH3)3CCH2OH, yields 2-methyl-2- butene as the major product. Outline a mechanism showing all steps in its formation.
Propose the structures for hydrocarbons (and give the organic reaction) that give the following products on oxidative cleavage with KMnO 4 or O 3 .
Chapter 14 Solutions
Organic Chemistry
Ch. 14.1 - Prob. 1PCh. 14.2 - Give the structures of both 1, 2 and 1, 4 adducts...Ch. 14.2 - Prob. 3PCh. 14.2 - Give the structures of both 1, 2 and 1, 4 adducts...Ch. 14.3 - Prob. 5PCh. 14.3 - Prob. 6PCh. 14.5 - Predict the product of the following Diels–Alder...Ch. 14.5 - Prob. 8PCh. 14.5 - Which of the following dienes have an s-cis...Ch. 14.5 - Predict the product of the following Diels–Alder...
Ch. 14.6 - Prob. 11PCh. 14.6 - Prob. 12PCh. 14.7 - Prob. 13PCh. 14.7 - Prob. 14PCh. 14.8 - Which of the following compounds would you expect...Ch. 14.SE - Prob. 16VCCh. 14.SE - Show the product of the Diels–Alder reaction of...Ch. 14.SE - Prob. 18VCCh. 14.SE - Prob. 19VCCh. 14.SE - Prob. 20MPCh. 14.SE - Prob. 21MPCh. 14.SE - In light of your answer to Problem 14-21 propose...Ch. 14.SE - Luminol, which is used by forensic scientists to...Ch. 14.SE - Prob. 24MPCh. 14.SE - Give IUPAC names for the following compounds:Ch. 14.SE - Prob. 26APCh. 14.SE - Prob. 27APCh. 14.SE - Electrophilic addition of Br2 to isoprene...Ch. 14.SE - Prob. 29APCh. 14.SE - Prob. 30APCh. 14.SE - Predict the products of the following...Ch. 14.SE - 2,3-Di-tert-butyl-1,3-butadiene does not undergo...Ch. 14.SE - Prob. 33APCh. 14.SE - Prob. 34APCh. 14.SE - Prob. 35APCh. 14.SE - Prob. 36APCh. 14.SE - Rank the following dienophiles in order of their...Ch. 14.SE - Prob. 38APCh. 14.SE - Prob. 39APCh. 14.SE - Prob. 40APCh. 14.SE - Although the Diels–Alder reaction generally...Ch. 14.SE - Prob. 42APCh. 14.SE - Tires whose sidewalls are made of natural rubber...Ch. 14.SE - Prob. 44APCh. 14.SE - Prob. 45APCh. 14.SE - Prob. 46APCh. 14.SE - Would you expect allene, H2C = C = CH2, to show a...Ch. 14.SE - The following ultraviolet absorption maxima have...Ch. 14.SE - Prob. 49APCh. 14.SE - -Ocimene is a pleasant-smelling hydrocarbon found...Ch. 14.SE - Draw the resonance forms that result when the...Ch. 14.SE - Prob. 52APCh. 14.SE - Treatment of 3,4-dibromohexane with strong base...Ch. 14.SE - Prob. 54APCh. 14.SE - Prob. 55APCh. 14.SE - Prob. 56APCh. 14.SE - Prob. 57APCh. 14.SE - Prob. 58APCh. 14.SE - Hydrocarbon A, C10H14, has a UV absorption at...Ch. 14.SE - Prob. 60APCh. 14.SE - Prob. 61APCh. 14.SE - Prob. 62APCh. 14.SE - Prob. 63APCh. 14.SE - Prob. 64APCh. 14.SE - The double bond of an enamine (alkene + amine) is...Ch. 14.SE - Prob. 66AP
Knowledge Booster
Similar questions
- Enamines normally react with methyl iodide to give two products: one arising from alkylation at nitrogen and the second arising from alkylation at carbon. For example, Heating the mixture of C-alkylation and N-alkylation products gives only the product from C-alkylation. Propose a mechanism for this isomerization.arrow_forwardBicyclo-2,5-heptadiene can be prepared in two steps from cyclopentadiene and vinyl chloride. Provide a mechanism for each step.arrow_forward5. Compound A, C 10H 18O, undergoes reaction with dilute H 2SO 4 at 50 °C to yield a mixture of two alkenes, C 10H 16. The major alkene B, gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Which of the following reactions are correct.arrow_forward
- When 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_forwardUsing benzene and any necessary organic or inorganic reagents, suggest efficient syntheses of (a) Isobutylbenzene, C6H5CH2CH(CH3)2 (b) (2,2-Dimethylpropyl)benzene, C6H5CH2C(CH3)3arrow_forwardGive the major product of the monobromination of n-butane (or butane) in the presence of light or heat. Propose a mechanism for this reaction and name the product. Provide 2 reactions in the termination step.arrow_forward
- the organic compound 2-heptanone, belonging to the ketone family, is responsible for the strong penetrating odor in Roquefort cheeses. Starting from acetylene as the starting reagent, propose a synthesis line with the reaction mechanisms involved for the synthetic obtaining of 2-heptanone and use it as a food additive in analogous cheeses.arrow_forwardBased on what you know about the relative stabilities of alkyl radicals and benzylic radicals, predict the product of addition of HBr to 1-phenylpropene in the presence of a free-radical initiator. Propose a mechanism for this reaction.arrow_forwardCompound A, C 10H 18O, undergoes reaction with dilute H 2SO 4 at 50 °C to yield a mixture of two alkenes, C 10H 16. The major alkene B, gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Which of the following reactions are correct. Can be more than one answerarrow_forward
- Give a proposal on the synthesis methods of CoSO4.7H2Oarrow_forwardPredict the products for the hydrohalogenation reaction of 1-methyl-1,3-cyclohexadiene with 1 equivalent of HBr in thermodynamic conditions.arrow_forward(2E,4Z,6Z,8E)-decatetraene has been cyclized to give 7,8-dimethy-1,3,5-cyclooctatriene. Predict the manner of ring-closure conrotatory or disrotatory for both thermal and photochemical reactions, and predict the stereochemistry of product in each case. Show how to get the answerarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning