This chapter continues the expansion of organic synthesis begun in Chapter 7. We

Question

This chapter continues the expansion of organic synthesis begun in Chapter 7. We still have very few reactions for making molecules at our disposal, basically just additions and the El, E2, S_N1, and S_N2 reactions. Nonetheless, it is possible to devise simple routes to target molecules and even to craft a few multistep sequences. Propose a synthesis of each of the following compounds starting with 2-bromobutane. If you propose a reaction that will give a mixture of products, be sure to all products from that reaction. 2-butene 2-butanol butane 2-methoxybutane Predict the product(s) for each of the reactions shown. Indicate the pathway (S_N1, S_N2, E1, or E2) formation of each product.

Explanation / Answer

8.2

a) elimination reaction of 2-bromobutane gives trans 2-butene (major), cis 2-butene and 1-butene. trans 2-butene is major because cis 2-butene is less stable due to steric hinderence and 1-butene is least stable because it is least substituted product.

b). Heating 2-bromo butane (chiral racemic) with water gives racemic 2- butanol through SN1 (carbocation mechanism) or SN2 (transition state).

c) 1-butene and 2-butene obtained in (a) is hydrogenated catalytically H2/ Pd/C to give n-butane.

d) SN2 reaction of 2-bromo butane with sodium methoxide results in racemic 2-methoxy butane.

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