Another raw material for the production of hexamethylenediamine is butadiene derived from thermal and catalytic cracking of petroleum. Propose reagents and experimental conditions for the conversion of butadiene to hexamethylenediamine. CH,=CHCH=CH, CICH,CH=CHCH,CI Butadiene 1,4-Dichloro-2-butene N=CCH,CH=CHCH,C=N H,N(CH,),NH, 3-Hexenedinitrile 1,6-Hexanediamine (Hexamethylenediamine)

Another raw material for the production of hexamethylenediamine is butadiene derived from thermal and catalytic cracking of petroleum. Propose reagents and experimental conditions for the conversion of butadiene to hexamethylenediamine. CH,=CHCH=CH, CICH,CH=CHCH,CI Butadiene 1,4-Dichloro-2-butene N=CCH,CH=CHCH,C=N H,N(CH,),NH, 3-Hexenedinitrile 1,6-Hexanediamine (Hexamethylenediamine)

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions

Section: Chapter Questions

Problem 20.42P: Bicyclo-2,5-heptadiene can be prepared in two steps from cyclopentadiene and vinyl chloride. Provide...

See similar textbooks

Similar questions

Classify the following dienes and polyenes as isolated, conjugated, cumulated, or some combination of theseclassifications.(a) cycloocta-1,4-diene (b) cycloocta-1,3-diene (c) cyclodeca-1,2-diene(d) cycloocta-1,3,5,7-tetraene (e) cyclohexa-1,3,5-triene (benzene)
Classify the following dienes and polyenes as isolated, conjugated, cumulated, or some combination of theseclassifications. ) cycloocta-1,3,5,7-tetraene
What’s the role of NaBH4 in Oxymercuration-Demercuration of cyclohexene?
α-Terpinene, C10H16, is a pleasant-smelling hydrocarbon that has been isolated from oil of marjoram. On hydrogenation over a palladium catalyst, α-terpinene reacts with 2 molar equivalents of H2 to yield a hydrocarbon, C10H20. On ozonolysis, followed by reduction with zinc and acetic acid, α-terpinene yields two products, glyoxal and 6-methyl-2,5- heptanedione. (a) How many degrees of unsaturation does a-terpinene have? (b) How many double bonds and how many rings does it have? (c) Propose a structure for a-terpinene.
Classify the following dienes and polyenes as isolated, conjugated, cumulated, or some combination of theseclassifications. cyclohexa-1,3,-diiene (benzene)
Reaction of HBr with 3-methylcyclohexene yields a mixture of four products: cis-and trans-1-bromo-3-methylcyclohexane and cis-and trans-1-bromo-2-methylcyclohexane. The analogous reaction of HBr with 3-bromocyclohexene yields trans-1, 2-dibromocyclohexane as the soleproduct. Draw structures of the possible intermediates, and then explain why only a single product is formed in this reaction.
Show that the [4 + 4] cycloaddition of two butadiene molecules to give cycloocta1,5-diene is thermally forbidden but photochemically allowed
Both cis- and trans-2-methylcyclohexanol undergo dehydration in warm sulfuric acid to give 1-methylcyclohexene as the major alkene product. These alcohols can also be converted to alkenes by tosylation using TsCl and pyridine, followed by elimination using KOC(CH3)3 as a strong base. Under these basic conditions, the tosylate of cis-2-methylcyclohexanoleliminates to give mostly 1-methylcyclohexene, but the tosylate of trans-2-methylcyclohexanol eliminates to give only 3-methylcyclohexene. Explain how this stereochemical difference in reactants controls a regiochemical difference in the products of the basic elimination, but not in the acid-catalyzed elimination.
What would be the expected major product when cyclooctene reacts with Cl2 in aqueous solution with H2O as the solvent?
(a) Cyclohexa-1,3-diene can be converted into a tetrasubstituted haloalkane when reacted with bromine in ether. Write a balanced chemical equation for the reaction that occurs and state the expected observation. (b) Compound A and B are alkenes with the same molecular formula C5H10. Compound A is a branched-chain alkene while compound B is a straight-chain alkene. The reaction between compound A with hydrogen bromide produces major product C which is optically active. (i) Draw TWO (2) possible structures for compound B. (ii) Outline the mechanism for the reaction between compound A with hydrogen bromide to form major product C. (iii) Name the product formed when compound A undergoes bromination reaction.
The bicyclic alkene P can be prepared by thermal electrocyclic ring closure from cyclodecadiene Q or by photochemical electrocyclic ring closure from cyclodecadiene R. Draw the structures of Q and R, and indicate the stereochemistry of the process by which each reaction occurs.
draw structures for all the isolated, conjugated, and cumulated dienes of molecular formula C5H8.