The structure of the major product obtained from ( R , R ) isomer of the amine is to be drawn. Concept introduction: In Hoffman’s elimination reaction, the less substituted alkene as the more favourable product, whereas according to Zaitsev rule more substituted alkenes are considered as more favourable product. The notations E or Z are used to describe the geometry around the double bond of an alkene, whereas nomenclature cis or trans is used to describe the relative configurations ( R or S ) . In the cis or trans compound, the molecular formula remains same but arrangement of the atoms in space is different. Cis or trans and E or Z are not interrelated to each other.

Question

Draw the structure of the product obtained when this amine is treated with excess iodomethane and then heated with Ag0 (Hoffman elimination) ball & stick labels • Consider EZ stereochemistry of alkenes. • Draw only the elimination product, do not the leaving group. • In cases where there is more than one answer, just draw one. ChemDoodle

Answer 1

Question

Chapter 19.15, Problem 19.22P

(a)

Interpretation Introduction

Interpretation:

The structure of the major product obtained from (R,R) isomer of the amine is to be drawn.

Concept introduction:

In Hoffman’s elimination reaction, the less substituted alkene as the more favourable product, whereas according to Zaitsev rule more substituted alkenes are considered as more favourable product. The notations E or Z are used to describe the geometry around the double bond of an alkene, whereas nomenclature cis or trans is used to describe the relative configurations (R or S). In the cis or trans compound, the molecular formula remains same but arrangement of the atoms in space is different. Cis or trans and E or Z are not interrelated to each other.

(b)

Interpretation Introduction

Interpretation:

The formation of the Zaitsev product using stereochemical drawings of the transition states are to be shown.

Concept introduction:

In Hoffman’s elimination reaction, the less substituted alkene as the more favourable product, whereas according to Zaitsev rule more substituted alkenes are considered as more favourable product. The notations E or Z are used to describe the geometry around the double bond of an alkene, whereas nomenclature cis or trans is used to describe the relative configurations (R or S). In the cis or trans compound, the molecular formula remains same but arrangement of the atoms in space is different. Cis or trans and E or Z are not interrelated to each other.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

Draw the structure of the product obtained when this amine is treated with excess iodomethane and then heated with Ag0 (Hoffman elimination) ball & stick labels • Consider EZ stereochemistry of alkenes. • Draw only the elimination product, do not the leaving group. • In cases where there is more than one answer, just draw one. ChemDoodle

What kinds of halides cannot be used to alkylate an amine? Why not? a.Tertiary halides form alkenes on elimination. b.Aryl halides unless activated by electron-withdrawing groups c.Halides with beta-alkyl groups are sterically hindered. d. all of the above

Why can you not use this reaction to make a secondary amine? a) Alkyl halides are weak electrophiles.b) Primary amines are weak nucleophiles.c) The primary amine is too nucleophilic, so over-reaction will occur.d) The secondary amine product is more nucleophilic than the primary amine reactant, so over-reaction will occur.