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

a) Put these three common types of carbonyl compound in order of decreasing reactivity ester amide acid chloride b) For the least reactive, show the interconversion to its other resonance form: How does this electron delocalisation make it stable? c) For the most reactive, draw the mechanism of its undergoing hydrolysis (reaction with H2O): Why makes this type of carbonyl so reactive to nucleophiles?

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

a) Put these three common types of carbonyl compound in order of decreasing reactivity ester amide acid chloride b) For the least reactive, show the interconversion to its other resonance form: How does this electron delocalisation make it stable? c) For the most reactive, draw the mechanism of its undergoing hydrolysis (reaction with H2O): Why makes this type of carbonyl so reactive to nucleophiles?

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.

When the (R,R) isomer of the amine shown is treated with an excess of methyl iodide, then silver oxide, then heated, the majorproduct is the Hofmann product.) Some Zaitsev product is also formed. It has the (E) configuration. When the same amine is treated with mCPBA and heated, theZaitsev product has the (Z) configuration. Use stereochemical drawings of the transition states to explain these observations