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DIRECTIONS: The following questions are based on topics covered in class. Read the problems carefully and follow directions. Make sure everything is CLEARLY LABELED. Synthetic analysis. Predict the products, showing proper stereochemistry where appropriate, of the following reactions of 1-hexyne. (a) 1 equiv HBr, CCI4 (b) 1 equiv. Cl2, CC14 (c) 2 Lindlar catalyst CH3(CH2)3CECH (d) 1. NaNH2, NH3 2. CH3Br, THF (e) H20, H2S04 HgSO4

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(a) 1 equiv HBr, ccl4 H3C(H2Ca C-CH2 Br (b) 1 equiv. Cl2, CCl4 H3C(H2C)3 Cl CI H3C(H2C)3 H H2 Lindlar catalyst CH3(CH2)3CCH d

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