ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
6th Edition
ISBN: 9781260826791
Author: SMITH
Publisher: MCG
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Chapter 26.9, Problem 20P
Interpretation Introduction

Interpretation: The structure of 2-ketohexose is to be determined.

Concept introduction: The aldehyde carbonyl group and ketone carbonyl group reduces to alcohol on reaction with NaBH4. The C=O group changes to COH on reduction.

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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]
PROBLEM 4 Solved Show how 1-butanol can be converted into the following compounds: a. PROBLEM 5+ b. d. -C= N
Which alkene is the major product of this dehydration? OH H2SO4 heat

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