HW17Key - Graded Homework Assignment#17 Answer Key Deadline...

Info icon This preview shows pages 1–2. Sign up to view the full content.

View Full Document Right Arrow Icon
Graded Homework Assignment #17 Answer Key Deadline : 9:00 a.m., Friday, 4/16/10 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This assignment is worth a total of 40 raw points. 1. (20 points; each box is worth 5 points) When an unknown hydrocarbon A (molecular formula C 8 H 14 ) is exposed to HCl, a single product, B (molecular formula C 8 H 15 Cl), can be isolated after the reaction is complete. B is optically inactive . When A is treated with BH 3 , followed by H 2 O 2 , NaOH, H 2 O, a mixture of two products, C and D , is isolated. C and D both have molecular formula C 8 H 16 O. The mixture of C and D is optically inactive, but when C and D are separated from each other, the isolated compounds are each optically active . Finally, when A is exposed to O 3 , followed by H 2 O 2 , the only product isolated is 6-oxooctanoic acid (structure shown below). Given this information, propose structures for the unknown compounds A , B , C , and D . Write your answers in the appropriate boxes in the reaction scheme provided below.
Image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 2
This is the end of the preview. Sign up to access the rest of the document.