zn, ch3cooh with halides

[BrownieDDD]

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Dat destroyer Orgo


1,2-dibromocyclohalide -----> cyclopentane

which reagent is the best for the conversion?

a) -OH
b) Zn, Ch3COOH
c) Na, NH3
d) ch30- / ch3oh
e) (ch3)3co-k+ / (ch3)3coh

answer: b

i've never seen this reaction in my life....does anyone have a link to where i can find this online? or any insight???

 

[sacapuntas]

1,2- dibromocyclohalide...is that supposed to be 1,2 dibromocyclopentane or am I having a brain fart?

If it is 1,2 dibromocyclopentane, the bromines are replaced with hydrogen, a reduction. You just have to chose the best reducing agent and B is the only option...at least that is what I think but I haven't done o-chem 2 and don't have DAT destroyer anymore to check this so that is somewhat of a guess.

 

[Tangymoose]

a) -OH
This will cause an alcohol to form (SN reactions)

b) Zn, Ch3COOH
Reducer. Usually anything with Zn + acid is a reducer. This reaction is similar to the Clemmensen reduction.

c) Na, NH3
Also a reducer but only reduces alkyne to trans alkene. Its a "weak" reducer

d) ch30- / ch3oh
CH3O- is a strong base. More likely to undergo elimination.

e) (ch3)3co-k+ / (ch3)3coh
I'm guessing elimination because of the bulky, strong base.

You can answer this question purely by process of elimination. Only 2 answers are actually reducers, which we are looking for since the answer ends in -ane.

 

[Tunaman]

Destroyer year this came from & problem #?

 

[BrownieDDD]

sorry yes i messed up the reagent: it's 1,2-dibromocyclopentane --> pentane

Dat destroyer Orgo odyssey Ch. 5 # 4 (2012) edition