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EGB 2022M Short Answer (Topics 1-5)

1. (8 marks)

(i) Specify which of the following species are nucleophiles, and which are electrophiles. (4 marks)

H₂O, HO^-, ⁺CH₃, NH₃, HCl, CH₃OH, H⁺, R(C=O)OR’

(ii) Which is likely to be the most nucleophilic and the most electrophilic? (2 marks)

(iii) Rank the following in order of increasing leaving group ability i.e., from the highest to lowest pK_aH. (2 marks)

H₂O, Cl^-, R^-, HO^-

2. Consider orbital hybridisation to explain why borane (BH₃) is electrophilic. (8 marks)

3. The compound shown below binds to a protein. State the non-covalent interaction that is likely to dominate between the protein and three parts of the compound. Each interaction should be different, and you should identify the functional group of each part of the compound you choose, in addition to the amino acids that typically form these interactions. (8 marks)

PRR 2022M Short Answer (Topics 6-8)

4.

(i) Indicate whether each pair of structures shown below represent enantiomers, diastereomers, or are the same. (6 marks)

(ii) State which C atoms in Compound A are stereocenters and assign the absolute configuration for each. (2 mark)