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Chapter 7: Problem 4

Draw a structural formula for a hydrocarbon with the given molecular formula that undergoes hydroboration-oxidation to give the indicated product. (a) \(\mathrm{C}_{7} \mathrm{H}_{10}\) O=CCC1CCC(O)C1 (b) \(\mathrm{C}_{7} \mathrm{H}_{12}\) O=[N+]([O-])C1CCC(CCO)C1

Short Answer

Expert verified
Question: Identify the hydrocarbon with the given molecular formula that can undergo hydroboration-oxidation to produce the following products: (a) O=CCC1CCC(O)C1 (b) O=[N+]([O-])C1CCC(CCO)C1 Answer: (a) The hydrocarbon with the molecular formula \(\mathrm{C}_{7} \mathrm{H}_{10}\) that can undergo hydroboration-oxidation to produce the given product is: C=CCC1CCC=C1 (b) The hydrocarbon with the molecular formula \(\mathrm{C}_{7} \mathrm{H}_{12}\) that can undergo hydroboration-oxidation to produce the given product is: C1CCC(CCO)C1

Step by step solution

01

We have been given the SMILES representation of the product and we can see that it has an alcohol functional group. Since hydroboration-oxidation results in the formation of alcohol, our goal is to identify an appropriate alkene in the hydrocarbon to perform the hydroboration-oxidation reaction. #Step 2: Work backwards from the product to hydrocarbon#

By keeping in mind the hydroboration-oxidation behaviour, we need to add a hydrogen atom to the alcohol group and remove the oxygen atom. This will lead us to the original alkene that would have undergone the hydroboration-oxidation reaction. #Step 3: Write the structural formula for the hydrocarbon#
02

Based on our analysis, the hydrocarbon with the molecular formula \(\mathrm{C}_{7} \mathrm{H}_{10}\) that can undergo hydroboration-oxidation to produce the given product is: C=CCC1CCC=C1 (b) \(\mathrm{C}_{7} \mathrm{H}_{12}\) O=[N+]([O-])C1CCC(CCO)C1 #Step 1: Analyze the product#

In this case, we have been given the SMILES representation of the product which has a nitrate functional group attached. Since hydroboration-oxidation results in the formation of alcohols, we need to identify the starting material that would have led to the formation of the given product with a nitrate functional group. #Step 2: Work backwards from the product to hydrocarbon#
03

By analyzing the product, we need to add an oxygen atom and a hydrogen atom to the nitrate group to convert it back into an alcohol group. We are not concerned with the nitrate group, as it is not a product of hydroboration-oxidation reactions. #Step 3: Write the structural formula for the hydrocarbon#

Based on our analysis, the hydrocarbon with the molecular formula \(\mathrm{C}_{7} \mathrm{H}_{12}\) that would have undergone hydroboration-oxidation to produce the given product is: C1CCC(CCO)C1

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Most popular questions from this chapter

Draw structural formulas for the major product(s) formed by reaction of 3 -hexyne with each of these reagents. (Where you predict no reaction, write NR.) (a) \(\mathrm{H}_{2}\) (excess)/ \(\mathrm{Pt}\) (b) \(\mathrm{H}_{2} /\) Lindlar catalyst (c) \(\mathrm{Na}\) in \(\mathrm{NH}_{3}(l)\) (d) \(\mathrm{BH}_{3}\) followed by \(\mathrm{H}_{2} \mathrm{O}_{2} / \mathrm{NaOH}\) (e) \(\mathrm{BH}_{3}\) followed by \(\mathrm{CH}_{3} \mathrm{COOH}\) (f) \(\mathrm{BH}_{3}\) followed by \(\mathrm{CH}_{3} \mathrm{COOD}\) (g) \(\mathrm{Cl}_{2}(1 \mathrm{~mol})\) (h) \(\mathrm{NaNH}_{2}\) in \(\mathrm{NH}_{3}(l)\) (i) \(\mathrm{HBr}(1 \mathrm{~mol})\) (j) \(\mathrm{HBr}(2 \mathrm{~mol})\) (k) \(\mathrm{H}_{2} \mathrm{O}\) in \(\mathrm{H}_{2} \mathrm{SO}_{4} / \mathrm{HgSO}_{4}\)

Using your reaction roadmap as a guide, show how to convert the starting trans-alkene to the cis-alkene in high yield. Show all intermediate molecules synthesized along the way.

Write the products of the following sequences of reactions. Refer to your reaction roadmap to see how the combined reactions allow you to "navigate"between the different functional groups. For example, in part (a) below, notice how the reaction sequence results in the conversion of an alkyne into a haloalkane in two steps.

Show how to convert 1-butyne to each of these compounds. (a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C}=\mathrm{C}^{-} \mathrm{Na}^{+}$ (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C}=\mathrm{CD}\) (c) *C=C(C)C (d) C=C(C)C

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