As a scientist working in a government lab, you have been given full control over the production of a new compound. The compound was isolated from the Eastern cypress tree, a tree which grows throughout 75% of the world and reaches maturity in 2-3 years. It was found that only the needles contain the compound of interest (shown to the right).

Choose whether you would extract from the natural source

or chemically synthesize the compound. Explain and justify three reasons that support the choice you made and one reason, that is different than anything you mentioned, why your choice might not be the best – detail required in all answers. (9 marks)

An unknown compound, A, was isolated from the bark of a conifer tree growing in northern British Columbia. This compound, C_8H_14, was found to be optically active because of two stereo genic carbon atoms. When it was hydrogenated with a platinum catalyst, compound B (C_8H_16) was formed. Hot, basic permanganate solution oxide/ed A to two different compounds: C (CH_2O_2) and D (C_7H_12O). Compound C was not optically active and had a very strong and broad IR absorption centred around 3000 cm and a strong medium width JR absorption centred at 1750 cm^-1. Compound D had a strong IR absorption at 1730 cm^-1. It was still optically active, with two stereo genic carbon atoms. Deduce possible structures for compounds A, B, C, and D. Give the reasons for your choices. Note that there may be more than one correct answer for A, B, and D.

Multiple choice. An optically active compound has the formula C3H14. The compound is hydrogenated with excess hydrogen in the preserve of Pd catalyst. The new compound is not optically active. Which of these structures could be the compound? Explain your choice for part A.

(i) See the NMR spectrum[A]. The unknown compound is an aromatic compound whose molecular formula is C_8H_9Br. Draw the structure of the unknown and name the compound based on its NMR spectrum. Explain the reasons that support your conclusion. (ii) See the spectra [B]. Determine the structure and write name of the unknown compound based on its IR, NMR ad Mass spectra in [B]. Explain the reasons that support your conclusion. There are many ways to prepare alcohols. The following reactions show some of methods to synthesize alcohols. Fill in blanks [A] - [E] with appropriate reagent(s)/compounds to complete each reaction.