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Chapter 9: Problem 56

Using your roadmap as a guide, show how to convert butane into 2-butyne. Show all reagents and all molecules synthesized along the wav.

Short Answer

Expert verified
Question: Outline the step-by-step conversion of butane into 2-butyne, briefly mentioning the reagents used and molecules formed in each step. Answer: The conversion involves the following steps: 1. Formation of 2-chlorobutane via radical halogenation using Cl2 and light (hv). 2. Formation of 2,3-dichlorobutane through another radical halogenation using Cl2 and light (hv). 3. Formation of 2-buten-1-al by an E2 elimination reaction using alcoholic KOH. 4. Partial reduction of 2-buten-1-al to 2-buten-1-ol using NaBH4 as a reducing agent. 5. Formation of 2-butyne through a dehydration reaction using P2O5.

Step by step solution

01

Formation of 2-chlorobutane

To form 2-chlorobutane, we will react butane with a chlorine molecule in the presence of light (hv) to promote a radical halogenation reaction. The reaction is as follows: \[C_4H_{10} + Cl_2 \xrightarrow{hv} C_4H_9Cl + HCl\]
02

Formation of 2,3-dichlorobutane

Proceeding from 2-chlorobutane, we will now perform another radical halogenation reaction by adding another chlorine molecule and light (hv). The reaction is as follows: \[C_4H_9Cl + Cl_2 \xrightarrow{hv} C_4H_8Cl_2 + HCl\]
03

Formation of 2-buten-1-al

We will now use alcoholic KOH for an E2 elimination reaction to form a double bond in the molecule. Alcoholic KOH will deprotonate the hydrogen atoms from the beta-carbon, and the chlorine atoms will also leave at the same time. The reaction is as follows: \[C_4H_8Cl_2 + 2KOH \to C_4H_6O + 2KCl + 2H_2O\]
04

Partial Reduction of 2-buten-1-al

Now, we will reduce the aldehyde group to an alcohol with the use of NaBH4 as the reducing agent. The reaction is as follows: \[C_4H_6O + NaBH_4 \to C_4H_8O + NaB(OH)_3\]
05

Formation of 2-butyne

Lastly, to obtain 2-butyne, we need to eliminate water molecules from the 2-buten-1-ol. To do this, we will use P2O5 in a dehydration reaction. The reaction is as follows: \[C_4H_8O + P_2O_5 \to C_4H_6 + P(OH)_5\] By following these steps, we have successfully converted butane into 2-butyne, showcasing each reagent and molecule synthesized along the way.

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Most popular questions from this chapter

Each of these compounds can be synthesized by an \(\mathrm{S}_{\mathrm{N}} 2\) reaction. Suggest a combination of haloalkane and nucleophile that will give each product. (a) \(\mathrm{CH}_{3} \mathrm{OCH}\) (b) \(\mathrm{CH}_{3} \mathrm{SH}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{PH}_{2}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CN}\) (e) \(\mathrm{CH}_{3} \mathrm{SCH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{3}\) (f) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{NH}^{+} \mathrm{Cl}^{-}\) (h) \((R)-\mathrm{CH}_{3} \mathrm{CHCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) (i) \(\mathrm{CH}_{2}=\mathrm{CHCH}_{2} \mathrm{OCH}\left(\mathrm{CH}_{3}\right)_{2}\) (j) \(\mathrm{CH}_{2}=\mathrm{CHCH}_{2} \mathrm{OCH}_{2} \mathrm{CH}=\mathrm{CH}_{2}\) (k) ClC1CCCCN1 (1) C1COCCO1

Draw a structural formula for the product of each \(\mathrm{S}_{\mathrm{N}} 2\) reaction. Where configuration of the starting material is given, show the configuration of the product.

Account for the relative rates of solvolysis of these compounds in aqueous acetic acid.

Elimination of HBr from 2-bromonorbornane gives only 2-norbornene and no 1-norbornene. How do you account for the regioselectivity of this dehydrohalogenation? In answering this question, you will find it helpful to look at molecular models of both 1-norbornene and 2-norbornene and to analyze the strain in each.

Which isomer of 1-bromo-3-isopropylcyclohexane reacts faster when refluxed with potassium tert-butoxide, the cis isomer or the trans isomer? Draw the structure of the expected product from the faster reacting compound.
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