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BIOC10001: Biological Chemistry 1A Data Handling
Assignment 2023-2024
Answers sheet

This answer sheet must be handed submitted via Blackboard by 14:00 (2 pm) on Friday 5th January 2024. Late submissions will attract a penalty. You can edit this file with Word/Office/most word processors. Please make sure you add your name above. Where you are asked to submit structures and/or mechanisms, if you prefer you can draw these out by hand and insert images into this document.
All questions contribute equal marks. This assignment contributes 10% to the overall Unit mark.

Question 1:
a. Answer: The IR spectrum represents: ……………………………………..
Explanation:

b. IR spectrum #2 Answer: ……………………………….
Explanation:

IR spectrum #3 Answer ………………………………
Explanation:

IR spectrum #4 Answer …………………………….
Explanation:

(c) Now draw the chemical mechanism for the reaction of compound A with compound B, naming the product formed. What pH conditions would favour this reaction

Question 2:
(a) Explain how these isomers could be distinguished by mass spectroscopy.
Answer:

(b). Show the structures of positive ion fragments of 2-heptanone that account for mass spectrum peaks of m/z=43 and m/z=99 respectively.
Answer:

Question 3:
(a)Interpret the IR spectrum, explaining which peaks arise from which functional groups in the compound.

(b)Explain the chemical shift, integral and multiplicity of each peak in the 1H NMR spectrum and the chemical shifts in the 13C NMR spectrum.

(c)Combine all of these data to describe a possible structure for the compound.

Question 4:
(a) Draw a predicted 1H NMR spectrum for Compound X. You should include peak integration data in your spectra.

(b) The researchers collect a 13C NMR spectrum of the isolated compound. They are surprised to discover that the spectrum lacks the expected peaks at 71.5 ppm, 20.6 ppm, and 16 ppm. Based on these findings draw a revised structure of the isolated compound and describe how it differs from compound X.

Question 5:
For the following incomplete mechanism of an enzymatic reaction:
(i)Identify the substrate/product components (1), (2) & (3).

(1) = …………………………………………….

(2)= …………………………………………….

(3)= ……………………………………………

(ii)Draw the structure of the modified form of the co-factor labelled (4).

(iii)Add curly arrows to the overall diagram to show the flow of electrons throughout this mechanism. (You can either add these to the figure or draw out the mechanism by hand and add the arrows, then upload a picture of your diagram).

Question 6:
a)Sketch the two additional tautomeric forms of this molecule.

b)Draw the 1H spectra of all three tautomeric forms.