Solved: Show how you would synthesize the following compounds, starting with acetylene

Chapter 0, Problem 9-37

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Show how you would synthesize the following compounds, starting with acetylene and any compounds containing no more than four carbon atoms. (a) hex-1-yne (b) hex-2-yne (c) cis-hex-2-ene (d) trans-hex-2-ene (e) 1,1-dibromohexane (f) 2,2-dibromohexane (g) pentanal, (h) pentan-2-one, (i) (j) meso-butan-2,3-diol (k) 2-methylhex-3-yn-2-ol 9-38 When treated with hydrogen and a platinum catalyst, an unknown compound X absorbs 5 equivalents of hydrogen to give n-butylcyclohexane. Treatment of X with an excess of ozone, followed by dimethyl sulfide and water, gives the following products: 1;2-3,4-dibromohexane CH3CH2CH2CH2CHO CH3CO