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Chapter 1: Problem 74

When CCC(C)(C)C undergoes rearrangement, the major rearranged ion formed is likely to be

Short Answer

Expert verified
Answer: The major rearranged ion formed is: H H H | | | H-C-C=C | C-H | | H H and its SMILES notation is: CCC=C(C)C

Step by step solution

01

Convert SMILES notation to structural formula

Begin by converting the SMILES notation "CCC(C)(C)C" into a structural formula to help visualize the molecule: H H H | | | H-C-C-C-C-H | H-C-C-H | | H H
02

Identify the possible rearrangement mechanisms

The given hydrocarbon structure may undergo a variety of rearrangement mechanisms, such as 1,2-hydride shifts, 1,2-methyl shifts, or ring expansions. However, based on the structure of the given compound, the most likely rearrangement mechanism that can occur here is the 1,2-methyl shift (since there is no hydrogen atom present on the tertiary carbon atom and no ring to undergo ring expansion).
03

Analyze the 1,2-methyl shift process

A 1,2-methyl shift occurs when a methyl group moves from one carbon atom to an adjacent carbon atom, resulting in a rearranged ion formation. In this case, the methyl shift will occur at the tertiary carbon (the carbon with three other attached carbon atoms). The shift will result in a change in the hybridization state of the involved carbon atoms, from sp3 to sp2.
04

Determine the major rearranged ion formed

After the 1,2-methyl shift, the major rearranged ion formed will be the one that follows the migration of the methyl group from the tertiary carbon to one of its adjacent carbon atoms. The ion's structure will look like this: H H H | | | H-C-C=C | C-H | | H H
05

Write the SMILES notation for the major rearranged ion

Finally, we can write the SMILES notation for the major rearranged ion: CCC=C(C)C

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Most popular questions from this chapter

The correct increasing order of electron donating effect of \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-,\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-\) and \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\) groups when attached to benzene or unsaturated system is (a) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-<\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-<\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\) (b) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-<\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-<\mathrm{CH}_{3}-\mathrm{CH}_{2}-\) (c) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-<\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-<\mathrm{CH}_{3}-\mathrm{CH}_{2}-\) (d) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}<\mathrm{CH}_{3}-\mathrm{CH}_{2}-<\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\)

A meso compound (a) is an achiral molecule, which contain chiral carbons. (b) contains a plane of symmetry or a centre of symmetry. (c) is optically inactive due to internal compensation. (d) is characterized by all the above.

The boiling point of \(\mathrm{CH} 3 \mathrm{OH}\) is \(65^{\circ} \mathrm{C}\), while the boiling point of \(\mathrm{CH} 3 \mathrm{SH}\) is only \(6^{\circ} \mathrm{C}\). Explain this difference in boiling point.

Match the elements of Column I to elements of Column II. There can be single or multiple matches. Column I (a) Free radicals (b) Photochemical reaction (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CHCH}_{3}\) (d) No bond resonanceColumn II (p) halogenation of alkanes (q) homolytic cleavage (r) hyperconjugation (s) chain reaction

which of the following statements is not correct? (a) Resonance and tautomerism describe the same phenomenon. (b) A group with a + I effect, attached to a carbocation, increases the stability of the carbocation. (c) Weaker the acid, stronger is its conjugate base. (d) The \(-\mathrm{OH}\) and \(-\mathrm{NH}_{2}\) group attached to an aromatic ring exert \(+\mathrm{M}\) effect.
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