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Primary (1") alcohols often show a peak in their mass spectra at \(m / z=31\). Suggest a structure for this fragment.

Short Answer

Expert verified
The fragment is \( CH_2OH^+ \).

Step by step solution

01

Understanding the Mass Spectrum

Primary (1") alcohols often exhibit a peak at \( m/z = 31 \). This indicates that there is a fragment with a molecular weight of 31 that is common in the mass spectra of primary alcohols.
02

Determine Possible Fragment

The peak at \( m/z = 31 \) in primary alcohols typically corresponds to a specific ion formed during the mass spectrometry process. This fragment is often the result of the loss of water (\( H_2O \), which has a mass of 18) from the molecular ion.
03

Identify the Fragment Structure

For a primary alcohol, the removal of an \( OH \) group (17 m/z) along with a hydrogen atom results in the formation of the \( CH_2OH^+ \) fragment. This fragment corresponds to a peak at \( m/z = 31 \).
04

Verify the Fragment

The \( CH_2OH^+ \) ion is a common fragment observed at \( m/z = 31 \), as it maintains a stable structure after the initial cleavage of bonds in a primary alcohol under mass spectrometry.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Primary Alcohols
Primary alcohols are a type of alcohol where the hydroxyl group (\(OH\)) is attached to a carbon atom that is also bonded to at most one other carbon atom. This specific arrangement makes primary alcohols generally more reactive than secondary and tertiary alcohols.

In mass spectrometry, primary alcohols often provide distinct peaks that help in identifying their structure. One such characteristic peak occurs at \(m/z = 31\), which can be pivotal in deducing the fragmentation pattern of the alcohol. The knowledge of where the hydroxyl group is located can aid in predicting and understanding the fragmentation patterns observed.

Primary alcohols like methanol and ethanol serve as simple yet effective examples in experimental scenarios due to their straightforward structures and predictable mass spectrometry outcomes.
Fragmentation
Fragmentation in mass spectrometry involves breaking a molecule into smaller pieces, or fragments. This typically occurs after the molecule is ionized, and can reveal much about the molecule's structure based on the pattern of fragments.

For primary alcohols, the fragmentation often leads to a peak at \(m/z = 31\). This is because a common fragmentation pathway involves the loss of the water molecule (\(H_2O\)), which weighs 18 units, from the parent alcohol molecule. The resulting fragment is the \(CH_2OH^+\) ion, illustrating how breaking certain parts of the molecule can yield recognizable peaks on a mass spectrum.

Understanding fragmentation patterns is crucial for interpreting mass spectra since these provide a fingerprint for verifying molecular structures. Predicting potential fragments helps chemists to confirm the identity of unknown compounds through their characteristic peaks.
Ion Formation
Ion formation in mass spectrometry begins with the ionization of a molecule. This process involves either adding or removing electrons to create ions, which can then be analyzed based on their mass-to-charge ratio (\(m/z\)).

In the context of primary alcohols, the protonated molecule often loses water, leading to the formation of the \(CH_2OH^+\) ion. This ion, responsible for the common \(m/z = 31\) peak in mass spectra of primary alcohols, results when a hydrogen atom and the hydroxyl group detaches from the alcohol.

The stability of the resulting ion can influence its detectability. A stable ion, like \(CH_2OH^+\), is more likely to form repeatedly, contributing to a strong, distinct peak on the mass spectrum, making identification simpler and more reliable.

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Most popular questions from this chapter

Suppose you have two bottles, labeled ketone \(\mathbf{A}\) and ketone \(\mathrm{B}\). You know that one bottle contains \(\mathrm{CH}_{3} \mathrm{CO}\left(\mathrm{CH}_{2}\right)_{5} \mathrm{CH}_{3}\) and one contains \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CO}\left(\mathrm{CH}_{2}\right)_{4} \mathrm{CH}_{3}\), but you do not know which ketone is in which bottle. Ketone A gives a fragment at \(m / z=99\) and ketone B gives a fragment at \(m / z=113 .\) What are the likely structures of ketones \(A\) and \(B\) from these fragmentation data?

Propose possible structures consistent with each set of data. Assume each compound has an \(s p^{3}\) hybridized \(\mathrm{C}-\mathrm{H}\) absorption in its IR spectrum, and that other major IR absorptions above \(1500 \mathrm{~cm}^{-1}\) are listed. a. A compound having a molecular ion at 72 and an absorption in its IR spectrum at \(1725 \mathrm{~cm}^{-1}\) b. A compound having a molecular ion at 55 and an absorption in its IR spectrum at \(-2250 \mathrm{~cm}^{-1}\) c. A compound having a molecular ion of 74 and an absorption in its IR spectrum at \(3600-3200 \mathrm{~cm}^{-1}\)

Treatment of anisole \(\left(\mathrm{CH}_{3} \mathrm{OC}_{6} \mathrm{H}_{5}\right)\) with \(\mathrm{Cl}_{2}\) and \(\mathrm{FeCl}_{3}\) forms \(\mathrm{P}\), which has peaks in its mass spectrum at \(\left.\mathrm{m} / \mathrm{z}=142 \mathrm{(M}\right)\), \(144(\mathrm{M}+2), 129\), and \(127 . \mathrm{P}\) has absorptions in its IR spectrum at \(3096-2837\) (several peaks), 1582 , and \(1494 \mathrm{~cm}^{-1}\). Propose possible structures for \(\mathrm{P}\).

What is the mass of the molecular ion formed from compounds having each molecular formula: (a) \(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{O} ;\) (b) \(\mathrm{C}_{10} \mathrm{H}_{20}\); (c) \(\mathrm{C}_{8} \mathrm{H}_{8} \mathrm{O}_{2} ;\) (d) methamphetamine \(\left(\mathrm{C}_{10} \mathrm{H}_{15} \mathrm{~N}\right)\) ?

Like alcohols, ethers undergo \(\alpha\) cleavage by breaking a carbon-carbon bond between an alkyl group and the carbon bonded to the ether oxygen atom; that is, the red \(\mathrm{C}-\mathrm{C}\) bond in \(\mathrm{R}-\mathrm{CH}_{2} \mathrm{OR}^{\prime}\) is broken. With this in mind, propose structures for the fragments formed by \(\alpha\) cleavage of \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCH}_{2} \mathrm{OCH}_{2} \mathrm{CH}_{3}\). Suggest a reason why an ether fragments by \(\alpha\) cleavage.

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