Show how you would use a Wittig reaction to synthesize 1-phenylbuta-1,3-diene.

(a) In an acid-catalyzed hydration, one of the following 10 carbon alkynes is expected to produce a single hydration product? Select the correct alkyne and draw the structure of the hydration product that is formed from this alkyne. (I) 2-decyne; (II) 3-decyne; (III) 4-decyne; (IV) 5-decyne; (V) none of these will give a single hydration product. (b) The reaction shown below gives Compound X as the major product. The mass spectrum of X is shown. Br2, H20 Compound X 100 - MS-IW-5644 80 60 40 - 20 - 20 40 60 80 100 120 140 160 180 200 220 m/z Considering the reactions of alkynes and the MS data, de duce which of following structures corresponds to X: Br Br HO, IV V I II II Support your answer with a reaction mechanism for fomation of X and identification of relevant peaks in the mass spectrum. 12 Relative Intensity

Provide the structure of the two organic product(s) which results when 2-bromo-2-methylbutane is treated with sodium ethoxide.

Cleavage of alkenes to carbonyl compounds (Ozonolysis, Periodate, KMnO4 reactions)

Enamines can serve as enolate surrogates in reactions at the a-carbon. In the reaction sequence, the structures of the enamine addition product – the initial zwitterion and its neutral tautomer – are shown. Draw the structures of the two reactants forming these intermediates, and draw the structure of the final product, obtained via hydrolysis of the neutral intermediate. initial zwitterionic intermediate neutral intermediate tautomerization Reactants H,0 hydrolysis product Draw the two reactants. Draw the hydrolysis product. Select Draw Rings More Erase Select Draw Rings More Erase H H

Show how the reaction of an allylic halide with a Grignard reagent might be used to synthesize the following hydrocarbons.(a) 5-methylhex-1-ene