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 has the greatest molar heat of combustion?  

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

Which of the statements below correctly describes the chair conformations of   

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 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  

Name the structure.  

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

Which compound has the highest pKa?