{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}


Nucleophilic_substitution - LCU Nucleophilic substitution...

Info iconThis preview shows pages 1–2. Sign up to view the full content.

View Full Document Right Arrow Icon
LCU Nucleophilic substitution and elimination – competing reactions Alkyl halides (halogenoalkanes) are R-X where X is Cl, Br, I 1 o , 2 o and 3 o refer to the number of carbon atoms attached to the α or head carbon that carries the halogen. Alternatively, it can be seen as the number of hydrogens attached to the α carbon. 1 o one C attached to α C two hydrogens 2 o two C attached to α C one hydrogen 3 o three C attached to α C no hydrogens F and Cl bonds with C are strongly polar and F and Cl alkyl halides have permanent dipoles. Br and I alkyl halides are less polar. As the halogen becomes bigger, the dipole is due more to the number of electrons present around the halogen atom (with I this is 53, a considerable amount of negativity). The basic reaction of alkyl halides is substitution where a negative ion attacks the alkyl halide. Fluoroalkanes are very unreactive despite having the largest dipole. Several reasons apply: overall reaction is endothermic due to strength of the C-F bond; that F is a poor leaving group because F - is a strong-ish base and forms a weak acid HF etc. The rate of reaction I>Br>Cl is related to activation energy. The C-I bond is weak and so activation energy to break it is low. Substitution reactions involve an attacking group and a leaving group. The attacking group is either a negative ion (anion) e.g. OH - and CN - or another group with an unbonded pair of electrons. There is a displacement series for the nucleophiles and leaving groups. Ones on the left will, as nucleophiles, displace those on the right as leaving groups.
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 2
This is the end of the preview. Sign up to access the rest of the document.

{[ snackBarMessage ]}