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State the number of sets of equivalent hydrogens in each compound and the number of hydrogens in each set. (a) 3-Methylpentane (b) \(2,2,4\)-Trimethylpentane

Short Answer

Expert verified
Answer: (a) In 3-Methylpentane, there are four sets of equivalent hydrogens: - Set 1: 3 hydrogens - Set 2: 6 hydrogens - Set 3: 2 hydrogens - Set 4: 2 hydrogens (b) In \(2,2,4\)-Trimethylpentane, there are two sets of equivalent hydrogens: - Set 1: 9 hydrogens - Set 2: 2 hydrogens

Step by step solution

01

Draw the structure of 3-Methylpentane

To draw the structure of 3-Methylpentane, we need to understand that it is a 5-carbon chain (pentane) with a methyl (CH3) group attached to the third carbon. The structure of 3-Methylpentane is: ``` CH3-CH2-CH(CH3)-CH2-CH3 ```
02

Identify equivalent hydrogens

Now that we have drawn the structure, we can identify the sets of equivalent hydrogens. The sets of equivalent hydrogens in 3-Methylpentane are as follows: 1. The three hydrogens in the methyl group on the third carbon (CH(CH3) group). 2. The six hydrogens in the other two methyl groups (CH3 groups) at the ends of the molecule. 3. The two hydrogens in the second carbon (CH2 group next to the CH(CH3) group). 4. The two hydrogens in the fourth carbon (CH2 group next to the CH(CH3) group).
03

State the number of hydrogens in each set

Now that we've identified the equivalent hydrogens, we can state the number of hydrogens in each set: Set 1: 3 hydrogens Set 2: 6 hydrogens Set 3: 2 hydrogens Set 4: 2 hydrogens So, there are four sets of equivalent hydrogens in the 3-Methylpentane molecule. (b) \(2,2,4\)-Trimethylpentane
04

Draw the structure of \(2,2,4\)-Trimethylpentane

To draw the structure of \(2,2,4\)-Trimethylpentane, we need to understand that it is a 5-carbon chain (pentane) with a methyl (CH3) group attached to the second, second, and fourth carbon. The structure of \(2,2,4\)-Trimethylpentane is: ``` CH3 | CH3-C-CH2-C(CH3)-CH3 | CH3 ```
05

Identify equivalent hydrogens

Now that we have drawn the structure, we can identify the sets of equivalent hydrogens. The sets of equivalent hydrogens in \(2,2,4\)-Trimethylpentane are as follows: 1. The nine hydrogens in the three methyl groups (CH3 groups) attached to the second and fourth carbons (the two CH3 groups on the second carbon and the CH3 group on the fourth carbon). 2. The two hydrogens in the third carbon (CH2 group in the middle of the molecule).
06

State the number of hydrogens in each set

Now that we've identified the equivalent hydrogens, we can state the number of hydrogens in each set: Set 1: 9 hydrogens Set 2: 2 hydrogens So, there are two sets of equivalent hydrogens in the \(2,2,4\)-Trimethylpentane molecule.

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Most popular questions from this chapter

The \({ }^{13} \mathrm{C}-\mathrm{NMR}\) spectrum of 3 -methyl-2-butanol shows signals at \(\delta 17.88\left(\mathrm{CH}_{3}\right), 18.16\) \(\left(\mathrm{CH}_{3}\right), 20.01\left(\mathrm{CH}_{3}\right), 35.04\) (carbon-3), and \(72.75\) (carbon-2). Account for the fact that each methyl group in this molecule gives a different signal.

The natural abundance of \({ }^{13} \mathrm{C}\) is only \(1.1 \%\). Furthermore, its sensitivity in NMR spectroscopy (a measure of the energy difference between a spin aligned with or against an applied magnetic field) is only \(1.6 \%\) that of \({ }^{1} \mathrm{H}\). What are the relative signal intensities expected for the \({ }^{1} \mathrm{H}-\mathrm{NMR}\) and \({ }^{13} \mathrm{C}-\mathrm{NMR}\) spectra of the same sample of \(\mathrm{Si}\left(\mathrm{CH}_{4}\right)_{4}\) ?

The line of integration of the two signals in the \({ }^{1} \mathrm{H}-\mathrm{NMR}\) spectrum of a ketone with the molecular formula \(\mathrm{C}_{7} \mathrm{H}_{14} \mathrm{O}\) rises 62 and 10 chart divisions, respectively. Calculate the number of hydrogens giving rise to each signal and propose a structural formula for this ketone.

Calculate the index of hydrogen deficiency of these compounds. (a) Aspirin, \(\mathrm{C}_{9} \mathrm{H}_{8} \mathrm{O}_{4}\) (b) Ascorbic acid (vitamin \(\mathrm{C}\) ), \(\mathrm{C}_{6} \mathrm{H}_{8} \mathrm{O}_{6}\) (c) Pyridine, \(\mathrm{C}_{5} \mathrm{H}_{5} \mathrm{~N}\) (d) Urea, \(\mathrm{CH}_{4} \mathrm{~N}_{2} \mathrm{O}\) (e) Cholesterol, \(\mathrm{C}_{27} \mathrm{H}_{46} \mathrm{O}\) (f) Dopamine, \(\overline{\mathrm{C}}_{\mathrm{g}} \mathrm{H}_{11} \mathrm{NO}_{2}\)

Explain how to distinguish between the members of each pair of constitutional isomers based on the number of signals in the proton-decoupled \({ }^{13} \mathrm{C}\)-NMR spectrum of each member.

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