ps4 - formed. Draw the structures of the two products. (3)...

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
Chemistry 3590 Honors Organic Chemistry I PROBLEM SET #4 FALL, 2009 Please answer problems 42, 43, 45, 59 and 60 in Chapter 4 of Bruice, and the following questions: (1) Reaction of either 1-butene or 2-butene with HCl gives the same product, by way of the same intermediate. Yet the reaction of 1-butene with HCl is faster than that of 2-butene. (a) Explain the difference in reaction rate between 1-butene and 2-butene. (b) Using your explanation in (a), try to predict which would be more reactive towards HCl: cis -2-butene or trans -2-butene. (2) When 3-deuterio-1-methyl-1-cyclohexene undergoes hydroboration-oxidation (i.e., using borane in diethyl ether followed by alkaline hydrogen peroxide), two different isotopically labelled alcohols are
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: formed. Draw the structures of the two products. (3) Compounds A and B each have the molecular formula C 8 H 14 . Both A and B react with HBr to afford the same compound C , having the formula C 8 H 15 Br. Both A and B react with hydrogen in the presence of platinum to afford cyclooctane. What are the structures of A , B , C ? (4) Using the curved arrow formalism, propose a mechanism for the following reaction: N H N Br H Br + Br 2 (5) As you know, Adolph von Baeyer incorrectly predicted that cyclopentane would be more stable than cyclohexane, based on the regular polygon model. Using what youve learned in class about Van der Waals and torsional interactions, calculate the strain energy in the planar form of cyclopentane....
View Full Document

This note was uploaded on 11/10/2009 for the course CHEM 1570-001 taught by Professor Tadhgbegley during the Fall '08 term at Cornell University (Engineering School).

Ask a homework question - tutors are online