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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: cfr on November 09, 2010, 07:48:45 PM

Title: sn1 and sn2 reactions
Post by: cfr on November 09, 2010, 07:48:45 PM

hello,
i have some lab questions that I am confused about I hope you can help.

i have to arrange halides in order of decreasing reactivity toward ethanol silver nitrate

1-chlorobutane
2-chlorobutane
2-chloro-2-methylpropane
allyl chloride
benzyl chloride
chlorobenzene

also for reactivity with sodium iodide

1-bromobutane
2-bromobutane
2-bromo-2-methylpropane
allyl bromide
benzyl bromide
bromobenzene

thank you

Title: Re: sn1 and sn2 reactions
Post by: discodermolide on November 12, 2010, 10:01:52 AM

Quote from: cfr on November 09, 2010, 07:48:45 PM

hello,
i have some lab questions that I am confused about I hope you can help.

i have to arrange halides in order of decreasing reactivity toward ethanol silver nitrate

1-chlorobutane
2-chlorobutane
2-chloro-2-methylpropane
allyl chloride
benzyl chloride
chlorobenzene

also for reactivity with sodium iodide

1-bromobutane
2-bromobutane
2-bromo-2-methylpropane
allyl bromide
benzyl bromide
bromobenzene

thank you

These are all nucleophillic displacement reactions. The order is the same for both nucleophiles, nitro and iodide.
To start you off, chloro/bromobenzene is the least reactive towards both reagents

Title: Re: sn1 and sn2 reactions
Post by: Modestus on November 13, 2010, 01:50:51 PM

I might be able to give a hint, go back and look at the mechanisms in your text book and pay particular attention to steric crowding and the stability of carbon cations; also, it's always helped me to draw out the molecule. If that doesn't really help, post again and call me butt head. I'd be happy to explain in greater detail.  ;D