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SN1
(1) - two step process. rate=k[haloalkane]. best in polar protic solvent
Works with weak nucleophiles
favours tertiary (some secondary) haloalkanes - stable carbocation
racemisation: planar carbocation intermediate
![<p>(1) - two step process. rate=k[haloalkane]. best in polar protic solvent</p><p>Works with weak nucleophiles</p><p>favours tertiary (some secondary) haloalkanes - stable carbocation</p><p>racemisation: planar carbocation intermediate</p>](https://knowt-user-attachments.s3.amazonaws.com/9ad486da-67d0-4fe3-8a69-767776d721dc.jpg)
SN2
(2) - concerted process. rate=k[nucleophile][haloalkane]. best in polar aprotic solvent.
Inversion: 180degree attack to C-X sigma orbital
requires stong nucleophile
favours primary and secondary haloalkanes due to low steric interactions in trans state
![<p>(2) - concerted process. rate=k[nucleophile][haloalkane]. best in polar aprotic solvent.</p><p>Inversion: 180degree attack to C-X sigma orbital</p><p>requires stong nucleophile</p><p>favours primary and secondary haloalkanes due to low steric interactions in trans state</p>](https://knowt-user-attachments.s3.amazonaws.com/08b170ce-cdf1-4024-a262-5dc29828c9d0.jpg)
E1
(1) - two step process. rate=k[haloalkane]. best in polar protic solvent
favours formation of E-alkene (lower energy intermediate) and most substituted alkene
can use weak acid or bases
![<p>(1) - two step process. rate=k[haloalkane]. best in polar protic solvent</p><p>favours formation of E-alkene (lower energy intermediate) and most substituted alkene</p><p>can use weak acid or bases</p>](https://knowt-user-attachments.s3.amazonaws.com/f4e422e6-a121-48c0-acc2-7d5386bc7101.jpg)
E2
(2) - concerted process. rate=k[nucleophile][haloalkane]. best in polar aprotic solvent.
stereospecific - must go via antiperplanar trans state
regioselectivity is dependant on lareg/small base
favoursuse of strong bases
![<p>(2) - concerted process. rate=k[nucleophile][haloalkane]. best in polar aprotic solvent.</p><p>stereospecific - must go via antiperplanar trans state</p><p>regioselectivity is dependant on lareg/small base</p><p>favoursuse of strong bases</p>](https://knowt-user-attachments.s3.amazonaws.com/3e496f38-17dd-42b7-b0cd-a72b88e67c1b.jpg)
Regioselectivity
preferentially forming one structural isomer (regioisomer) over others
Polar protic solvents
Contain O-H or N-H bonds, allowing them to donate protons and form strong hydrogen bonds (aka. presence of an acidic hydrogen)
Polar aprotic solvents
Do not contain O-H or N-H bonds meaning they cannot donate protons but are still polar (there is an absence of an acidic hydrogen)