Chem 334 - Summer 1998 - Organic Chemistry I Dr. Carl C. Wamser

Answers for Chapter 9 Quiz (delivered by e-mail on 7/9)

To the Chemistry 334 class:

Below is the quiz for Chapter 9. The expectation is that you do your own work on this and return the answers to me by e-mail.

DO NOT return your answers by using the "reply" function, since that will send your answers to the whole discussion list. Double-check that the address for your e-mail answers is WamserC@pdx.edu

Return the answers no later than 7:00 pm this evening (Thurs, July 9).

I will post the answers shortly after that.

Note that all the answers can be done with words as opposed to structures.

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1. (5 points - 1/2 point each)

Indicate the products that would be expected when 2-propanol reacts with the following. In all cases, a reaction does occur. (You may need to look ahead in your text to determine correct names for some of the products.)

a) pyridinium chlorochromate - propanone

b) chromic acid - propanone

c) conc. sulfuric acid, 100o - propene

d) conc. hydrobromic acid - 2-bromopropane

e) methylmagnesium bromide - 2-propoxide + methane (an acid/base reaction)

f) phosphorus tribromide - 2-bromopropane

g) sodium metal - sodium 2-propoxide

h) sodium metal followed by methyl iodide - isopropyl methyl ether (or 2-methoxypropane)

i) t-butyl iodide - t-butyl isopropyl ether

j) p-toluenesulfonyl chloride - isopropyl p-toluenesulfonate

2a). (2 points)

Addition of methyllithium to cis-2,3-dimethyloxacyclopropane gives a compound with one stereocenter. Give the IUPAC name and predict the number of different stereoisomers formed and their relative abundance.

2b). (3 points)

Addition of ethyllithium to cis-2,3-dimethyloxacyclopropane gives a compound with two stereocenters. Give the IUPAC name and predict the number of different stereoisomers formed and their relative abundance.

(Note - the other two stereoisomers (R,R) & (S,S) could only come from additions to the trans isomer)