Destroyer Ochem Question

[Teeth12345]

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Hi,

I don't understand why the answer #168 is C. Wouldn't choice E also result in an E2 reaction that gives the less substituted alkene since the antiperiplanar H has to leave? Since the Br is at the end of the alkane chain, I thought that the less substituted alkene would always be formed.

Can someone please help with this? If you don't have the 2010 Destroyer, its #182 in the 2011 version.

Thanks

 

[wizi]

Hi,

I don't understand why the answer #168 is C. Wouldn't choice E also result in an E2 reaction that gives the less substituted alkene since the antiperiplanar H has to leave? Since the Br is at the end of the alkane chain, I thought that the less substituted alkene would always be formed.

Can someone please help with this? If you don't have the 2010 Destroyer, its #182 in the 2011 version.

Thanks

No, if you add C2H5OK, it would be SN2 because C2H5O-K+ is a strong base and nucleophile --> It can be either SN2 or E2. Plus, Br is on a primary carbon.

--> it def. goes for SN2 if you add C2H5OK.

 

[Teeth12345]

oooh ok, thanks!!