7.5 (a) Write equations to show how you expect compounds 7.24 to 7.28 to dissociate in aqueous solution. (b) Suggest how compound 7.29 will react with NaOH in aqueous solution. What salts would it be possible to isolate? (c) While it is convenient to draw the structures of compounds 7.24 to 7.28 as shown below, these suggest that the P and S atoms violate the octet rule. Redraw structures 7.24 and 7.25 so that the P atoms obey the octet rule. HO OH HO OH OH (7.24) (7.25) (7.26) OH H2N OH OH (7.27) (7.28) HO,C CO,H HO,C CO,H (7.29)

7.5 (a) Write equations to show how you expect compounds 7.24 to 7.28 to dissociate in aqueous solution. (b) Suggest how compound 7.29 will react with NaOH in aqueous solution. What salts would it be possible to isolate? (c) While it is convenient to draw the structures of compounds 7.24 to 7.28 as shown below, these suggest that the P and S atoms violate the octet rule. Redraw structures 7.24 and 7.25 so that the P atoms obey the octet rule. HO OH HO OH OH (7.24) (7.25) (7.26) OH H2N OH OH (7.27) (7.28) HO,C CO,H HO,C CO,H (7.29)

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter12: Structure Determination: Mass Spectrometry And Infrared Spectroscopy

Section12.SE: Something Extra

Problem 50AP

See similar textbooks

Similar questions

Which compound (i or ii) is the stronger base? Discuss your answer comprehensively by amongst other providing an acid base reaction for one of the compounds.
The cyclobutenyl dichloride below reacts with the powerful Lewis acid antimony pentafluoride in liquid SO2 at -75o to give a pale yellow solution that exhibits one singlet at 3.68 ppm in its 1H-NMR spectrum. The species in solution has been deduced to be the salt C8H12X2 where X is an hexahaloantimonate anion. Draw the cation part of the salt C8H12X2
Rank in order of Increasing Bronsted acidity the structures I, II and III.
1. Briefly discuss the important application of tris(triphenylphospine) chlorodium in organic chemistry.illustrating your answer with suitable example
A task is assigned to an undergraduate student to test two samples (known as compounds K and L) in the laboratory. She placed these two compounds through various scientific tests. She discovered that these compounds have the same molecular formula, C8H8O. When treated with 2,4-dinitrophenylhydrazine, all of these compounds produce brightly coloured precipitate, and both are reduced to an organic compound with the molecular formula C8H10O. However, compound K can be easily oxidized by chromic acid to formed compound N and vice versa for compound L. Furthermore, when both compounds reach with Fehling's solutions, they produce negative results. However, only compound K forms a silver mirror when it reacts with Tollen's reagent, and compound L does not. Identify the possible formulae for compounds K, L, and N by ignoring their possible isomerism. Indicate the formation of compound N from compound K. Predict the chemical reaction that occurs when compound L reacts with…
Provide the necessary product(s) (i), arrows (ii)and charges (iii).
Give the structure of compound 5 and compound 6
The Lewis structures of both pyridine and pyrrole have an electron pair on the nitrogen atom, suggesting that both substances might possess basic properties. However, the only pyridine reacts readily with HCl to form pyridinium chloride, while pyrrole is rather unreactive. Explain clearly, using relevant diagrams to illustrate/clarify your answer.
The following is an experimental account of the preparation of compound B from Phenylamine. 2cm3 of phenylamine are dissolved in 10cm3 of 0.5M hydrochloric acid in a test tube and cooled in an ice bath. 5cm3 of 0.2M sodium nitrate solution cooled to about 5o are added to the solution above and shaken. A salt A, C6H5N2Cl is formed, collected and dried. 1g of salt A is dissolved in 10cm3 of water, cooled and added drop by drop to a cold solution of 0.3g phenol in 5cm3 of 0.1M sodium hydroxide solution. B is precipitated, filtered, dried and the melting point determined. B is further crystallized twice and the melting point taken each time and found to be constant. Questions: (i) Give the name and suggest the colour of the precipitate B. Hence explain why it is necessary to recrystallize B several times. (ii) Why was it necessary to obtain a constant melting point for B?
The following is an experimental account of the preparation of compound B from Phenylamine. 2cm3 of phenylamine are dissolved in 10cm3 of 0.5M hydrochloric acid in a test tube and cooled in an ice bath. 5cm3 of 0.2M sodium nitrate solution cooled to about 5o are added to the solution above and shaken. A salt A, C6H5N2Cl is formed, collected and dried. 1g of salt A is dissolved in 10cm3 of water, cooled and added drop by drop to a cold solution of 0.3g phenol in 5cm3 of 0.1M sodium hydroxide solution. B is precipitated, filtered, dried and the melting point determined. B is further crystallized twice and the melting point taken each time and found to be constant. 1g of phenylamine yielded 1.2g of compound A. Calculate the percentage yield of the reaction.
The following is an experimental account of the preparation of compound B from Phenylamine. 2cm3 of phenylamine are dissolved in 10cm3 of 0.5M hydrochloric acid in a test tube and cooled in an ice bath. 5cm3 of 0.2M sodium nitrate solution cooled to about 5o are added to the solution above and shaken. A salt A, C6H5N2Cl is formed, collected and dried. 1g of salt A is dissolved in 10cm3 of water, cooled and added drop by drop to a cold solution of 0.3g phenol in 5cm3 of 0.1M sodium hydroxide solution. B is precipitated, filtered, dried and the melting point determined. B is further crystallized twice and the melting point taken each time and found to be constant. Why was it necessary to obtain a constant melting point for B?
The following is an experimental account of the preparation of compound B from Phenylamine. 2cm3 of phenylamine are dissolved in 10cm3 of 0.5M hydrochloric acid in a test tube and cooled in an ice bath. 5cm3 of 0.2M sodium nitrate solution cooled to about 5o are added to the solution above and shaken. A salt A, C6H5N2Cl is formed, collected and dried. 1g of salt A is dissolved in 10cm3 of water, cooled and added drop by drop to a cold solution of 0.3g phenol in 5cm3 of 0.1M sodium hydroxide solution. B is precipitated, filtered, dried and the melting point determined. B is further crystallized twice and the melting point taken each time and found to be constant. Give the structure of the product formed when an acidified solution of compound A is reacted with (i)Naphthalen-2-ol (2-naphthol) (ii) Sodium cyanide