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Chapter 7: Problem 31

Using your roadmap as a guide, show how to convert acetylene and bromoethane into 1-butene. All of the carbon atoms of the target molecule must be derived from the given starting materials. Show all intermediate molecules synthesized along the way.

Short Answer

Expert verified
Question: Outline the synthetic pathway to produce 1-butene from acetylene and bromoethane, showing all intermediate molecules. Answer: The synthesis of 1-butene from acetylene and bromoethane involves the following steps: 1. Convert acetylene to vinyl bromide by hydrobromination of acetylene with hydrobromic acid (HBr). 2. Convert bromoethane to ethylmagnesium bromide using a Grignard reaction with magnesium metal (Mg) in an ether solvent. 3. Form 1-butene by reacting vinyl bromide with ethylmagnesium bromide in a Grignard reaction.

Step by step solution

01

Acetylene to Vinyl Bromide

The first step is to convert acetylene (\(C_2H_2\)) to vinyl bromide (\(C_2H_3Br\)). We can achieve this by a hydrobromination reaction, where we add one mole of hydrobromic acid (\(HBr\)) across the triple bond of acetylene. This produces vinyl bromide: \( C_2H_2 + HBr \rightarrow C_2H_3Br \)
02

Bromoethane to Ethylmagnesium Bromide

In the second step, we will convert bromoethane (\(C_2H_5Br\)) into ethylmagnesium bromide (\(C_2H_5MgBr\)). This is achieved via a Grignard reaction, which involves the reaction of bromoethane with magnesium metal (\(Mg\)) in an ether solvent: \( C_2H_5Br + Mg \rightarrow C_2H_5MgBr \)
03

Formation of 1-Butene via Grignard Reaction

In the final step, we will convert vinyl bromide and ethylmagnesium bromide into 1-butene (\(C_4H_8\)). This can be achieved by the reaction between these two reactants in a Grignard reaction: \( C_2H_3Br + C_2H_5MgBr \rightarrow C_4H_8 + MgBr_2 \)
04

Overall Reaction

The overall reaction, which combines the three steps, can be represented as follows: \( C_2H_2 + HBr + C_2H_5Br + Mg \rightarrow C_4H_8 + MgBr_2 \) These are the key steps to convert acetylene and bromoethane into 1-butene, using all the carbon atoms from the given starting materials. Each step involved a sequence of reactions, and all intermediate molecules synthesized along the way were shown.

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Most popular questions from this chapter

Show how to convert 9-octadecynoic acid to the following. (a) \((E)-9-\) Octadecenoic acid (eliadic acid) (b) (Z)-9-Octadecenoic acid (oleic acid) (c) 9,10 -Dihydroxyoctadecanoic acid (d) Octadecanoic acid (stearic acid)

Complete each acid-base reaction and predict whether the position of equilibrium lies toward the left or toward the right. (a) $\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{CH}+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{O}^{-} \mathrm{Na}^{+} \underset{\mathrm{CH}_{3} \mathrm{CH}_{3} \mathrm{OH}}{\rightleftharpoons}$ (b) $\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{CCH}_{2} \mathrm{CH}_{2} \mathrm{OH}+\mathrm{Na}^{+} \mathrm{NH}_{2}{ }^{-} \underset{\mathrm{NH}_{3}(l)}{\rightleftharpoons}$ (c) $\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{C}^{-} \mathrm{Na}^{+}+\mathrm{CH}_{3} \mathrm{COH} \rightleftharpoons$ $$

Propose a synthesis of each compound starting from acetylene and any necessary organic and inorganic reagents. (a) 4-Octyne (b) 4-Octanone (c) cis-4-0ctene (d) trans-4-Octene (e) 4-Octanol (f) meso-4,5-0ctanediol

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Show how to prepare each compound from 1-heptene: (a) 1,2 -Dichloroheptane (b) 1-Heptyne (c) 1-Heptanol (d) 2-Octyne (e) cis-2-Octene (f) trans-2-Octene
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