The natural product halomon could theoretically arise from another naturally occurring compound known as myrcene. To accomplish this, a biochemical process that could deliver the synthetic equivalent of BrCi to all three double bonds would be required. (Chem Comm. 2014, 50, 13725) (a) Using three molar equivalents of BrCl, please provide a mechanism to account for the formation of the bracketed structure (you do not need to show stereochemistry in this mechanism) HB == (3 equiv) myrcene balomon

(d) Ozonolysis of 3,4-dimethyl-3-hexene gives compound D. (i) Write the reaction step for the formation of D by including the appropriate reagents. (ii) The mass spectrum of compound D shows a fragment ion peak at m/z 57. Propose the structure of this fragment ion. (ii) Identify the more stable resonance of the proposed structure in (ii).

Answer ALL parts of this question. (a) If ethyne is treated according to the following scheme, the final product is trans-pent-2-ene, as shown: H- (c) C-H (i) NaNH, / NH, (ii) CH₂Br (iii) NaNH, / NH (iv) CH₂CH₂Br (v) Na/NH3 H₂C H H CH₂CH3 Show the structures of the intermediates formed after each of the first four steps and identify the mechanism involved in steps (ii) and (iv). (b) If cis-pent-2-ene was wanted as the final product, how would step (v) in the sequence above must be modified? | The alkene shown in part (a) of this question could also be made by treating 2-bromopentane with base. It would be the major product out of three possible alkenes that could form. Give the structures of the two other alkenes that would form and comment on why trans-pent-2-ene is the major one that forms here.

Rank the following elements by electron affinity, from most positive to most negative EA value. Iodine, Neon, Sulfer, Arsenic, Sodium.