syn question

[datdat]

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this is from roadmap 3

it's hard to draw here but..

cyclopentane _Br + (CH3)3CO-Na+, (CH3)3COH --> cyclopentane==
|
CH3

(Br and CH3 is attached to C1 in cyclopentane)
and reacted w/ protic solvent and strong base ( i guess)
and it produces the product w/ c=c in C1 position in cyclopentane.

my question here is why not cyclopentene w/ methy attached to C1 like
---\\
--- /---CH3


it seems like base remove a H from CH3 but I think it can get rid of H from the ring so that it can form more substitued double bond..

can anyone help me out ?


why not cyclopentene--CH3?

 

[americanpierg]

this is from roadmap 3

it's hard to draw here but..

cyclopentane _Br + (CH3)3CO-Na+, (CH3)3COH --> cyclopentane==
|
CH3

(Br and CH3 is attached to C1 in cyclopentane)
and reacted w/ protic solvent and strong base ( i guess)
and it produces the product w/ c=c in C1 position in cyclopentane.

my question here is why not cyclopentene w/ methy attached to C1 like
---\\
--- /---CH3


it seems like base remove a H from CH3 but I think it can get rid of H from the ring so that it can form more substitued double bond..

can anyone help me out ?


why not cyclopentene--CH3?

i dont have the new destroyer with the roadmaps, and you equation doesnt make much sense... the methyl shouldn't have been cleaved off and the answer shouldn't be a cyclopentane nor a 1-methylcyclopentene. it should be a methylenecyclopentane. this occurs according to hoffman's rule and not zaitsev's rule because the base used is bulky and therefore sterically hindered. if they used CH3CH2O-Na+ in ethanol, then the answer would be a 1-methylcyclopentene



my question:

if it 1-methylpropanol is used, will substitution occur even if (CH3)3CO- Na+ is used (no solvent given)? ( will an ether form or will a propene form)??

 

[datdat]

because the base used is bulky and therefore sterically hindered. if they used CH3CH2O-Na+ in ethanol, then the answer would be a 1-methylcyclopentene



my question:

if it 1-methylpropanol is used, will substitution occur even if (CH3)3CO- Na+ is used (no solvent given)? ( will an ether form or will a propene form)??

got it..thanks...

as to your Q:

I think the alcohol will lose proton and form ether... am I right?