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Question 1 a) Benzenecarboxylic acid, commonly known as benzoic acid, has a pK, of 4.20. Find the pH of a 0.20 M solution of benzoic acid. b) Elemental analysis showed that a compound X had the empirical formula C6H7N. A simplified mass spectrum of X is shown below, together with an IR spectrum. 1.0 0.8 0.2 0.0 10 16 3500 m/2 Infrared Spectrum 2000 1500 77 1000 90 93 92 Mi: M Wy Wavenumbers (cm-1) i) Suggest chemical fragment identities for the mass spectrum peaks at m/z = 16 and m/z = 77 iv) A chemist reacted X with benzoyl chloride to produce a new organic compound, Y. Outline the mechanism of this reaction and clearly label compound Y. ii) Suggest chemical bond identities for the peaks at approx. (3400 and 3500) cm-¹ and (1500 and 1600) cm-¹. iii) Use your answers to i) and ii) to identify compound X and draw its structure. Include its IUPAC name. 10

Question 1 a) Benzenecarboxylic acid, commonly known as benzoic acid, has a pK, of 4.20. Find the pH of a 0.20 M solution of benzoic acid. b) Elemental analysis showed that a compound X had the empirical formula C6H7N. A simplified mass spectrum of X is shown below, together with an IR spectrum. 1.0 0.8 0.2 0.0 10 16 3500 m/2 Infrared Spectrum 2000 1500 77 1000 90 93 92 Mi: M Wy Wavenumbers (cm-1) i) Suggest chemical fragment identities for the mass spectrum peaks at m/z = 16 and m/z = 77 iv) A chemist reacted X with benzoyl chloride to produce a new organic compound, Y. Outline the mechanism of this reaction and clearly label compound Y. ii) Suggest chemical bond identities for the peaks at approx. (3400 and 3500) cm-¹ and (1500 and 1600) cm-¹. iii) Use your answers to i) and ii) to identify compound X and draw its structure. Include its IUPAC name. 10

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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Question 1 a) Benzenecarboxylic acid, commonly known as benzoic acid, has a pK₁ of 4.20. Find the pH of a 0.20 M solution of benzoic acid. b) Elemental analysis showed that a compound X had the empirical formula C6H₂N. A simplified mass spectrum of X is shown below, together with an IR spectrum. Relative Intensity 120 100 80 20 0.8 0.2 0.0 10 16 3500 20 30 3000 40 2500 50 m/z 60 Infrared Spectrum 2000 70 1500 77 80 1000 90 93 92 TR iv) A chemist reacted X with benzoyl chloride to produce a new organic compound, Y. Outline the mechanism of this reaction and clearly label compound Y. Wavenumbers (cm-1) i) Suggest chemical fragment identities for the mass spectrum peaks at m/z = 16 and m/z = 77 ii) Suggest chemical bond identities for the peaks at approx. (3400 and 3500) cm-¹ and (1500 and 1600) cm-¹. iii) Use your answers to i) and ii) to identify compound X and draw its structure. Include its IUPAC name. 10 500
Transcribed Image Text:Question 1 a) Benzenecarboxylic acid, commonly known as benzoic acid, has a pK₁ of 4.20. Find the pH of a 0.20 M solution of benzoic acid. b) Elemental analysis showed that a compound X had the empirical formula C6H₂N. A simplified mass spectrum of X is shown below, together with an IR spectrum. Relative Intensity 120 100 80 20 0.8 0.2 0.0 10 16 3500 20 30 3000 40 2500 50 m/z 60 Infrared Spectrum 2000 70 1500 77 80 1000 90 93 92 TR iv) A chemist reacted X with benzoyl chloride to produce a new organic compound, Y. Outline the mechanism of this reaction and clearly label compound Y. Wavenumbers (cm-1) i) Suggest chemical fragment identities for the mass spectrum peaks at m/z = 16 and m/z = 77 ii) Suggest chemical bond identities for the peaks at approx. (3400 and 3500) cm-¹ and (1500 and 1600) cm-¹. iii) Use your answers to i) and ii) to identify compound X and draw its structure. Include its IUPAC name. 10 500
Frequencies of important IR stretching vibrations CN (triple bond) CC (triple bond) C=C (aliphatic) C=N C=C (aromatic) C=0 C-O C-N O-H (alcohol) O-H (carboxylic acid) N-H C-H 2260-2220 2260-2100 1680-1600 1650-1550 1600 and 1500 1780-1650 1250-1050 1230-1020 3650-3200 3300-2500 3500 and 3400 3300-2700 Medium Medium to weak Medium Medium Strong to weak Strong Strong Medium Strong, broad Strong, very broad Medium. Broad Medium
Transcribed Image Text:Frequencies of important IR stretching vibrations CN (triple bond) CC (triple bond) C=C (aliphatic) C=N C=C (aromatic) C=0 C-O C-N O-H (alcohol) O-H (carboxylic acid) N-H C-H 2260-2220 2260-2100 1680-1600 1650-1550 1600 and 1500 1780-1650 1250-1050 1230-1020 3650-3200 3300-2500 3500 and 3400 3300-2700 Medium Medium to weak Medium Medium Strong to weak Strong Strong Medium Strong, broad Strong, very broad Medium. Broad Medium
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