5-Bromouracil causes mutations in DNA. Reason for this should be determined. Concept introduction: A parent DNA molecule consists of two poly nucleotide chains held together by bonds between complementary nitrogen bases. A base is nitrogen containing heterocyclic compound which is found in DNA and RNA. There are mainly five nitrogen bases. (1) Adenine (2) Guanine (3) Cytosine (4) Thymine (5) Uracil In DNA Adenine always makes a double bond with Thymine ( A = T ) and cytosine always makes triple bond with guanine ( G ≡ C ) Enol is a tautomer which exhibiting a special type of functional isomerism namely tautomerism. Tautomerism is a special type of functional isomerism in which isomers are in dynamic equilibrium with each other. Mutation is the process that results in change in the sequence of the DNA, and the compound which causes mutation is known as mutagenic compound.

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 26, Problem 36P

Interpretation Introduction

Interpretation:

5-Bromouracil causes mutations in DNA. Reason for this should be determined.

Concept introduction:

A parent DNA molecule consists of two poly nucleotide chains held together by bonds between complementary nitrogen bases.

A base is nitrogen containing heterocyclic compound which is found in DNA and RNA.

There are mainly five nitrogen bases.

(1) Adenine

(2) Guanine

(3) Cytosine

(4) Thymine

(5) Uracil

In DNA Adenine always makes a double bond with Thymine (A=T) and cytosine always makes triple bond with guanine (G≡C)

Enol is a tautomer which exhibiting a special type of functional isomerism namely tautomerism.

Tautomerism is a special type of functional isomerism in which isomers are in dynamic equilibrium with each other.

Mutation is the process that results in change in the sequence of the DNA, and the compound which causes mutation is known as mutagenic compound.

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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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