Author: Anonymous

For the following problem, use a separate sheet of paper for your answer and then upload your answers at the following link: https://canvas.dccc.edu/courses/28473/assignments/574397 Your work must be shown for full credit.     A C8H14 hydrocarbon (A) is reduced by sodium in liquid ammonia to a single C8H16 product (B). Both compounds undergo hydrogenation (using a Pt catalyst) to give 2,5-dimethylhexane. Ozonolysis of B followed by oxidative workup with H2O2 produces a single C4H8O2 carboxylic acid. Reaction of B with peroxybenzoic acid (C6H5CO3H) gives a chiral C8H14O product (C), but reaction with bromine gives an achiral C8H14Br2 product (D). Draw the structures for A, B, C, and D and show how you arrived at your answers using chemical equations.

Please answer the following question once you have uploaded your free response answer through the following link. https://canvas.dccc.edu/courses/28473/assignments/574397 [Select]

Which of the following alkenes would react the slowest with HBr?  

Which has the greatest molar heat of combustion?  

The reaction of meso-1,2-dibromo-1,2-diphenylethane with base gives a cis-1,2-diphenyl alkene while reaction of RR or SS 1,2-dibromo-1,2-diphenylethane gives a trans-1,2-diphenyl alkene. These results suggest the reaction is:  

Which of the statements below correctly describes the chair conformations of   

Name the structure.  

Which of the following is true about the reaction of 3-bromo-2-methylpentane with potassium methoxide? I.  The reaction is E2 elimination with anti-periplanar substrate configurationII. The reaction is concertedIII. The reaction produces the less substituted alkene due to size of the baseIV. A favorable yield requires high concentration of 3-bromo-2-methylpentane and methanol as the solvent  

Which compound has the highest pKa?  

What is the degree of unsaturation for the molecular formula C9O2H11NBr2?