The given observations are to be explained by the halogenation mechanism. Concept Introduction: ▸ Keto and enol form of carbonyl compounds are constitutional isomers. Inter-convertible keto and enol forms are tautomer. ▸ An enol and enolates can be formed by replacing the hydrogen at the α carbon. ▸ The α hydrogen can undergo halogen substitution at the α carbon in the presence of an acid and a base. ▸ When halogen substitution reaction takes place in the presence of an acid it is called as acid catalyzed halogenation reaction. ▸ When halogen substitution reaction takes place in the presence of a base it is called as base prompted halogenation reaction. ▸ In the base prompted halogenation reaction and acid catalyzed halogenation reaction slows rates are independent from the concentration of the halogens. ▸ The equimolar mixture of two enantiomers are called a racemic mixture. ▸ Racemization takes place at α hydrogen in the presence of acids or bases.

Question

bre The reaction sequence shown in Scheme 5 demonstrates the synthesis of a substituted benzene derivative Q. wolsd works 2 NH2 NaNO2, HCI (apexe) 13× (1 HNO3, H2SO4 C6H5CIN2 0°C HOTE CHINO₂ N O *O₂H ( PO Q Я Scheme 5 2 bag abouoqmics to sounde odi WEIC (i) Draw the structure of intermediate O. [2 marks] to noitsmot od: tot meinedogm, noit so oft listsb ni zaupaib bas wa (ii) Draw the mechanism for the transformation of aniline N to intermediate O. Spoilage (b) [6 marks] (iii) Identify the reagent X used to convert compound O to the iodinated compound [tom E P. vueimado oilovonsa ni moitos nolisbnolov ayd toes ai tedw nisiqx (iv) Identify the possible structures of compound Q. [2 marks] [2 marks] [shom 2] (v) bus noires goiribbeolovo xnivollot adj to subora sidab Draw the mechanism for the transformation of intermediate P to compound Q. [5 marks] vi (vi) Account for the regiochemical outcome observed in the reaction forming compound Q. [3 marks]

Answer 1

Question

Chapter 18, Problem 5PP

Interpretation Introduction

Interpretation:

The given observations are to be explained by the halogenation mechanism.

Concept Introduction:

▸ Keto and enol form of carbonyl compounds are constitutional isomers. Inter-convertible keto and enol forms are tautomer.

▸ An enol and enolates can be formed by replacing the hydrogen at the α carbon.

▸ The α hydrogen can undergo halogen substitution at the α carbon in the presence of an acid and a base.

▸ When halogen substitution reaction takes place in the presence of an acid it is called as acid catalyzed halogenation reaction.

▸ When halogen substitution reaction takes place in the presence of a base it is called as base prompted halogenation reaction.

▸ In the base prompted halogenation reaction and acid catalyzed halogenation reaction slows rates are independent from the concentration of the halogens.

▸ The equimolar mixture of two enantiomers are called a racemic mixture.

▸ Racemization takes place at α hydrogen in the presence of acids or bases.

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bre The reaction sequence shown in Scheme 5 demonstrates the synthesis of a substituted benzene derivative Q. wolsd works 2 NH2 NaNO2, HCI (apexe) 13× (1 HNO3, H2SO4 C6H5CIN2 0°C HOTE CHINO₂ N O *O₂H ( PO Q Я Scheme 5 2 bag abouoqmics to sounde odi WEIC (i) Draw the structure of intermediate O. [2 marks] to noitsmot od: tot meinedogm, noit so oft listsb ni zaupaib bas wa (ii) Draw the mechanism for the transformation of aniline N to intermediate O. Spoilage (b) [6 marks] (iii) Identify the reagent X used to convert compound O to the iodinated compound [tom E P. vueimado oilovonsa ni moitos nolisbnolov ayd toes ai tedw nisiqx (iv) Identify the possible structures of compound Q. [2 marks] [2 marks] [shom 2] (v) bus noires goiribbeolovo xnivollot adj to subora sidab Draw the mechanism for the transformation of intermediate P to compound Q. [5 marks] vi (vi) Account for the regiochemical outcome observed in the reaction forming compound Q. [3 marks]

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