Question

5di. In a synthesis experiment, benzoyl chloride was reacted with benzylamine to form N-benzylbenzamide. Answer the following questions. a. N-benzylbenzamide produced three peaks on its spectrum. In no particular order, these were m/z = 105, 211 and 77. Classify the fragments or compounds that are responsible for these three peaks. b. Justify why it is often the case that products from reactions must be recrystallised. c. The acid chloride, benzoyl chloride, was reacted with the amine, benzylamine, whilst sodium carbonate was present. Why was this important? Refer to the mechanism of the reaction in your justification. d. During the work up stage of this experiment, the product was washed with HCl and then deionised water. What was/were the reason(s) for this? ii. The table below represents the N-benzylbenzamide Carbon 13 Nuclear Magnetic Resonance data. Complete the table by first assigning a functional group to each corresponding carbon peak, then forecast the appearance of each signal in each department spectra for N-benzylbenzamide. Assignment: Dept 135: Dept 90: Dept 45: Carbon 13 NMR peak shift ?/ppm: Multiplicities: 167.44 S 138.27 S 134.40 S 131.54 D 128.77 D 128.58 D 127.89 D 127.59 D 127.02 D 43.98 T iii. Including the type of bending/stretch mode, assign each peak in the following table to a type of functional group. Present already are some of the Infrared spectra frequencies for N-benzylbenzamide. Type of bending/stretch mode: Functional group assigned to the peak: Frequency of the peak (in cm-1) 690 725 1640 2930 3060 3270

5di. In a synthesis experiment, benzoyl chloride was reacted with benzylamine to form N-benzylbenzamide. Answer the following questions.

a. N-benzylbenzamide produced three peaks on its spectrum. In no particular order, these were m/z = 105, 211 and 77. Classify the fragments or compounds that are responsible for these three peaks.
b. Justify why it is often the case that products from reactions must be recrystallised.
c. The acid chloride, benzoyl chloride, was reacted with the amine, benzylamine, whilst sodium carbonate was present. Why was this important? Refer to the mechanism of the reaction in your justification.
d. During the work up stage of this experiment, the product was washed with HCl and then deionised water. What was/were the reason(s) for this?

ii. The table below represents the N-benzylbenzamide Carbon 13 Nuclear Magnetic Resonance data.

Complete the table by first assigning a functional group to each corresponding carbon peak, then forecast the appearance of each signal in each department spectra for N-benzylbenzamide.

Assignment: Dept 135: Dept 90: Dept 45: Carbon 13 NMR peak shift ?/ppm: Multiplicities:
167.44 S
138.27 S
134.40 S
131.54 D
128.77 D
128.58 D
127.89 D
127.59 D
127.02 D
43.98 T

iii. Including the type of bending/stretch mode, assign each peak in the following table to a type of functional group. Present already are some of the Infrared spectra frequencies for N-benzylbenzamide.

Type of bending/stretch mode: Functional group assigned to the peak: Frequency of the peak (in cm-1)
690
725
1640
2930
3060
3270

5di. In a synthesis experiment, benzoyl chloride was reacted with benzylamine to form N-benzylbenzamide. Answer the following questions.

a. N-benzylbenzamide produced three peaks on its spectrum. In no particular order, these were m/z = 105, 211 and 77. Classify the fragments or compounds that are responsible for these three peaks.
b. Justify why it is often the case that products from reactions must be recrystallised.
c. The acid chloride, benzoyl chloride, was reacted with the amine, benzylamine, whilst sodium carbonate was present. Why was this important? Refer to the mechanism of the reaction in your justification.
d. During the work up stage of this experiment, the product was washed with HCl and then deionised water. What was/were the reason(s) for this?

ii. The table below represents the N-benzylbenzamide Carbon 13 Nuclear Magnetic Resonance data.

Complete the table by first assigning a functional group to each corresponding carbon peak, then forecast the appearance of each signal in each department spectra for N-benzylbenzamide.

Assignment: Dept 135: Dept 90: Dept 45: Carbon 13 NMR peak shift ?/ppm: Multiplicities:
167.44 S
138.27 S
134.40 S
131.54 D
128.77 D
128.58 D
127.89 D
127.59 D
127.02 D
43.98 T

iii. Including the type of bending/stretch mode, assign each peak in the following table to a type of functional group. Present already are some of the Infrared spectra frequencies for N-benzylbenzamide.

Type of bending/stretch mode: Functional group assigned to the peak: Frequency of the peak (in cm-1)
690
725
1640
2930
3060
3270

Added by Monique R.

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