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Unformatted text preview: Chapter 7 Dis ssion Section Problems I
l. Allylic halides have the following structure: we-.. cation I
b. Draw theiresonance structures of the allylic cations formed y ionization oftj following
c. Show the; products expected from SNI solvolysis of these h Iides in ethanol.
W 00 Cir Br (at) M
I BF 2. Predict the El products of elimination of the following compounds Label the majorl:uct. § ._
@ Br® © gCCH Br 3. CHALLENGE: D terium (D) is the isotope of hydrogen of mass nu ber 2 with a prot n and a
neutron' In its nu leus. The chemistry of deuterium Is nearly identic to the chemistry f
hydrogen except that the C- D bond Is slightly stronger than the I - H bond. Reacti n rates
tend to be lower if a C— D bond Is broken (as opposed to a C- H and) in a rate li/rTing step. This effect‘ Is called the kinetic isotope effect.
l a. Propose é mechanism to explain each product in the follovfing reaction.
I Lima—H olcolnql % ‘i' l. . l, elimImTIOﬂ subsnmlnoo
product product? - l . s l I
b. When the following deuterated compound reacts under
of formation of the substitution product' Is unchanged whit 1 ,"ie t l some conditions, the rate
he rate f formati n of the elimination product IS slowed by a factor of 7 Explain why e elimination rat is slower but the substitution rate Is unchanged. CD; ELI coféttcoLvar’se CDZZC-H-C £80m 4314
+ CH3 —EH——cD) YOK undnonq 3 c. A similar reaction takes place on heating the alkyl halide In an acetone/water mixture. ILO/ l
1 Br A Give a "\Lchanism for the formation of each product und these condition
predict how the rate of formation of each product will cha ge when the de halide reacts. Explain your prediction. 4. CHALLENGE: Wlten the following compound is treated with sodiu elimination pro cts are possible. Explain why the deuterated pro;
about a 7:1 rati . 5 CHALLENGE: Sotyolysis of bromomethylcyclopentane gives a camp 5 ‘ nd
erated methoxide in ethanol. two
uct predominat by H\qsc
/ \ ‘ ,H
‘H Iex product mixt e of the following ﬁve cofnpounds. Propose mechanisms to account for these products. Br
acme heat 0/0 ...
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- Winter '04
- Organic chemistry