a. CH3CH₂-C=C-CH₂CH₂CH3 ·00 C=C b. c. HC=C–CH,CH,–C=C–CH3 (HO)

Provide the major substitution product for the following reaction.

Draw the organic product(s) of the following reaction. H Aqueous H2SO4 H2N-N- ethanol

Draw the principal organic product of the following reaction. OEt OEt 1. NaOEt 2. H,C- 1. NaOEt — Br 2. Br H3O+ Δ

Show reagents and experimental conditions you might use to convert propyne into each product. (Some of these syntheses can be done in one step; others require two or more steps.)

S14

draw the products that could be formed in a reactionof benzene with 2hno3 in the presence of concentrated sulfuric acid

3. Ethanoic acid (vinegar) when diluted to low concentrations by water can be prepared from ethene by a) reduction with H2, followed by reaction with a strong oxidizer b) addition of HCL followed by reaction with H20 c) addition of H20 followed by reaction with a strong oxidizer d) addition of Br2 e) followed by reduction with H2

Draw the overall reaction of 1-butanol with HBr and H2SO4 to form 1-bromobutane.

In the acid catalyzed dehydration of 2,2-dimethyl-1-cyclohexanol, draw all possible alkenes, including those resulting from rearrangement.