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By Carey F., Sundberg R.

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The acidic reactions utilizing the general mechanism appear in Figure 3-26. Methanol and most primary alcohols follow an SN2 mechanism, while most other alcohols react by SN1. The SN1 reactions may involve rearrangement such as a hydride shift. Don’t forget that SN2 mechanisms involve an inversion of configuration. Chapter 3: Alcohols and Ethers: Not Just for Drinking and Sleeping Figure 3-26: General ROH + H+ steps for the conversion of an alco- ROH2 hol to an + + Xalkyl halide. R ROH2 R+ + H2O RX Figure 3-27 illustrates two examples using HCl/ZnCl2.

Backside attack occurs. ✓ Rearrangement is not possible. ✓ Polar aprotic solvents promote this type of reaction. Chapter 2: Remembering How We Do It: Mechanisms SN2 reactions lead to an inversion of stereochemistry. Nucleophilicity is decreased by protic solvents in SN2 reactions. The presence of a polar aprotic solvent is a clue that the mechanism is SN2. The main features of an E1 mechanism are as follows: ✓ Reactivity increases in the order Me < 1° << 2° < 3°. ✓ The major product is the most substituted alkene.

This means that the tail of the curved arrow must be at a lone pair or a bonding pair. ) The head of the curved arrow indicates where a lone pair is going or where a bond will form. Getting Ready for Some Basic Moves The tail of a curved arrow has two possible positions, and the head of a curved arrow has two possible positions. This means that, in theory, four combinations are possible. These combinations are ✓ Bond → lone pair ✓ Bond → bond ✓ Lone pair → bond ✓ Lone pair → lone pair The last combination doesn’t work, at least not in a single step, because it tends to force an atom to exceed an octet.

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