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A neutral compound A (C7H5N) is reduced to compound B (C7H9N) which is insoluble in water but dissolves in dilute hydrochloric acid. Compound B reacts with cold nitrous acid to produce compound C (C7H8O) with the evolution of a colourless gas. Oxidation of compound C produces compound D (C7H6O2). Compound D is also obtained when compound A is boiled with dilute sulphuric acid. Compound D reacts with phosphorus (V) chloride to produce compound E (C7H5ClO). Compound E reacts with compound C to produce compound F (C14H12O2) which is an ester. (a) Draw the structural formula of all the compounds A-F.  (b) Write a complete equation for the formation of compound B.  (c) Write a complete equation for the formation of compound C.  (d) Write a complete equation for the reactions that occur for compound D when compound A is boiled with dilute sulphuric acid.  (e) Write a complete equation for the formation of compound E.  (f) Write a complete equation for the formation of compound F. (g) Give the IUPAC name of compound A.  (h) Give the IUPAC name of compound B.  (i) Give the IUPAC name of compound C.  (j) Give the IUPAC name of compound D.  (k) Give the IUPAC name of compound E.

A neutral compound A (C7H5N) is reduced to compound B (C7H9N) which is insoluble in water but dissolves in dilute hydrochloric acid. Compound B reacts with cold nitrous acid to produce compound C (C7H8O) with the evolution of a colourless gas. Oxidation of compound C produces compound D (C7H6O2). Compound D is also obtained when compound A is boiled with dilute sulphuric acid. Compound D reacts with phosphorus (V) chloride to produce compound E (C7H5ClO). Compound E reacts with compound C to produce compound F (C14H12O2) which is an ester. (a) Draw the structural formula of all the compounds A-F.  (b) Write a complete equation for the formation of compound B.  (c) Write a complete equation for the formation of compound C.  (d) Write a complete equation for the reactions that occur for compound D when compound A is boiled with dilute sulphuric acid.  (e) Write a complete equation for the formation of compound E.  (f) Write a complete equation for the formation of compound F. (g) Give the IUPAC name of compound A.  (h) Give the IUPAC name of compound B.  (i) Give the IUPAC name of compound C.  (j) Give the IUPAC name of compound D.  (k) Give the IUPAC name of compound E.

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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A neutral compound A (C7H5N) is reduced to compound B (C7H9N) which is insoluble in water but dissolves in dilute hydrochloric acid. Compound B reacts with cold nitrous acid to produce compound C (C7H8O) with the evolution of a colourless gas. Oxidation of compound C produces compound D (C7H6O2). Compound D is also obtained when compound A is boiled with dilute sulphuric acid. Compound D reacts with phosphorus (V) chloride to produce compound E (C7H5ClO). Compound E reacts with compound C to produce compound F (C14H12O2) which is an ester.

  1. (a) Draw the structural formula of all the compounds A-F. 
  2. (b) Write a complete equation for the formation of compound B. 
  3. (c) Write a complete equation for the formation of compound C. 
  4. (d) Write a complete equation for the reactions that occur for compound D when compound A is boiled with dilute sulphuric acid. 
  5. (e) Write a complete equation for the formation of compound E. 
  6. (f) Write a complete equation for the formation of compound F.
  7. (g) Give the IUPAC name of compound A. 
  8. (h) Give the IUPAC name of compound B. 
  9. (i) Give the IUPAC name of compound C. 
  10. (j) Give the IUPAC name of compound D. 
  11. (k) Give the IUPAC name of compound E. 

 

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