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

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ii,iii,iv

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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