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Unformatted text preview: NAME: K I? Y Chemistry 130B Exam I January 29, 1996 43'! 1% 1% ‘£ 1 4,3: NlX' ERLEUCHTUNG H6HERE AUSBEUTEN! Laisse tomber La Renaissance; occupe-tol pluth du rendement. 3167):ch cpunocoqauvo,noaucrre Stanton; Pcaxquu [ Forget enlightenment! Just get the yields up! ] I. Predict the major product(s) from each of the following. Be sure to
indicate stereochemistry where appropriate. (a)
/o O ,_ Kt-o/VV 5 ——-————" /\/\/
2. KH, Ne’f’ 5 Yﬂio
0 c H H
/0 .. H30’Mw, Hw H
b 2 ~45,“ gc' @H + ﬁr
. ' 0m 6
ll 3. Namﬂdﬁ @i‘”'"" Z
0 Z, 930m @143):
430190 (C) A
L MCPBA, and; ‘3 lo
W Z. Name, on”, A 5 W 0H 0H ll. When solid sodium ethoxide is added to a benzene solution of n-hexyl iodide, no reaction
takes place. However, if 10 mol % of 15-crown-5 ether is then added, a reaction occurs. 8 (a) In the space below, provide a brief explanation of these events.
The 0mm 0W 50lublli3% (The NA 061” 50% (rim m En’ W. mm m Malia/Jr Minna. H95) ( “1’34” ) ( rm 5% )
5 (b) Show the overall transformation in equation form.
——’————~—> + /
/\/\/\¢ PM 190,5 /\/\/\06r ( W)
l ) y I
3 (c) Draw the structure of 15-crown-5 ether. F 0 ’1
. o 3
L o 0
1 (d) What type of mechanism is involved in the reaction that occurs? 5 N Z (52)
1(9) The reaction that takes place is a ‘name reaction’. What is it? Will/MSM W synM lll. Provide the following information as it relates to the hypothetical 1H NMR
spectrum below. a) Label the bottom axis, including the numbers for each marker, and the units.
b) Identify the ‘standard’ peak present at the far right of the spectrum. 0) Label the upfield and downfield regions of the spectrum. d) What is the relative ratio of protons shown? 9) Label the multiplicity for each absorption. ) What functional group might give rise to a peak in the region labelled ‘B’? G) olefin
‘f 20 IV. Suggest a short synthesis of compound X starting with bromocyclopentane and using
any reagent of up to two carbon atoms. Q—Br L O—Mjéf'é,’ X 5 5 0H 5
1°) 1. qul ...
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This note was uploaded on 02/01/2011 for the course CHEM 109B taught by Professor Aue during the Winter '08 term at UCSB.
- Winter '08
- Organic chemistry