For each reaction, give the expected substitution product, and predict whether the mechanism will be predominantly first order (SN1) or second-order (SN2). (a) isobutyl bromide + sodium methoxide

Predict the product(s) and provide the mechanism for each of the following reactions. (a) (b) LOCH₂CH3 HI HBr ? ?

5) Draw out the mechanism for the reaction given below, then generate a text description of the mechanism. OH excess

(a) Draw the mechanism for the formation of both of the enols that can be formed from A (use acetic acid & AcOH as the source of the protons) (b) Draw the mechanism of reaction of this enol with bromine to give product B

(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.

3) Predict the product for the following reaction. (CH3)2CHOH

(c) Compound 2F shown below is a tetra-substituted cyclooctatetraene. After heating 2F at 160 degree for 6 hours, researchers observed the formation of an isomer of 2F. Draw the isomer structure and provide a plausible mechanism to explain the formation of the isomers. 2F

(a) What product would you expect from cleavage of tetrahydrofuran with HI? (b) Outline a mechanism for the reaction.