The structures of the product when 1,3-butadiene reacts with the given dienophiles are to be given. Concept introduction: 舧 Diels–Alder is a type of organic reaction in which substituted alkene and conjugated diene react to form substituted cyclohexene derivative. It is a single step reaction. 舧 The general reaction of Diels–Alder is as follows: 舧 The Diels–Alder reaction is between a conjugate diene and a reactant containing double bond (dienophile) to form the product and the product is called adduct. 舧 Diels–Alder reactions are highly stereospecific. The configuration of dienophile is retained in the product and the reaction is syn addition. 舧 The dienes react with dienophiles in cis forms rather than trans forms. 舧 Endo and exo refers to the orientation of dienophile and its electron withdrawing group when it reacts with a diene in Diels–Alder reaction. 舧 The reaction with orientation of electron withdrawing group of dienophiles under the π orbitals of the diene, is Endo. 舧 The reaction with orientation of electron withdrawing group of dienophiles away from the π orbitals of the diene, is Exo 舧 Endo is favored in the transition state of Diels–Alder reaction because of its lower energy.

Question

Want to see the full answer?

Answer 1

Question

Chapter 13, Problem 40P

Interpretation Introduction

Interpretation:

The structures of the product when 1,3-butadiene reacts with the given dienophiles are to be given.

Concept introduction:

舧 Diels–Alder is a type of organic reaction in which substituted alkene and conjugated diene react to form substituted cyclohexene derivative. It is a single step reaction.

舧 The general reaction of Diels–Alder is as follows:

舧 The Diels–Alder reaction is between a conjugate diene and a reactant containing double bond (dienophile) to form the product and the product is called adduct.

舧 Diels–Alder reactions are highly stereospecific. The configuration of dienophile is retained in the product and the reaction is syn addition.

舧 The dienes react with dienophiles in cis forms rather than trans forms.

舧 Endo and exo refers to the orientation of dienophile and its electron withdrawing group when it reacts with a diene in Diels–Alder reaction.

舧 The reaction with orientation of electron withdrawing group of dienophiles under the π orbitals of the diene, is Endo.

舧 The reaction with orientation of electron withdrawing group of dienophiles away from the π orbitals of the diene, is Exo

舧 Endo is favored in the transition state of Diels–Alder reaction because of its lower energy.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Write structural formulas for the products that form when 1-butene reacts with each of the following reagents: (a) HI (b) H2, Pt (c) Dilute H2SO4, warm (d) Cold concentrated H2SO4 (e) Cold concentrated H2SO4, then H2O and heat (f) HBr (g) Br2 in CCl4 (h) Br2 in H2O (i) HCl (j) O3, then Me2S (k) OsO4, then NaHSO3/H2O (l) KMnO4, OH-, heat, then H3O+ (m) Hg(OAc)2 in THF and H2O, then NaBH4, OH- (n) BH3:THF, then H2O2, OH-

Give the structure, exclusive of stereochemistry, of the principal organic product formed on reaction of 2,3-dimethyl-1,3-butadiene with each of the following:(a) 2 mol H2, platinum catalyst(b) 1 mol HCl (product of 1,2-addition)(c) 1 mol HCl (product of 1,4-addition)(d) 1 mol Br2 (product of 1,2-addition)(e) 1 mol Br2 (product of 1,4-addition)(f) 2 mol Br2

(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.