Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 13: Problem 39

The \({ }^{1} \mathrm{H}-\mathrm{NMR}\) of compound \(\mathrm{R}, \mathrm{C}_{6 i} \mathrm{H}_{14} \mathrm{O}\), consists of two signals: \(\delta 1.1\) (doublet) and \(\delta 3.6\) (septet) in the ratio \(6: 1\). Propose a structural formula for compound \(R\) consistent with this information.

Short Answer

Expert verified
Answer: The proposed structural formula for compound R is hexyl methoxy methane (CH3-O-CH2-CH2-CH2-CH2-CH2-CH3).

Step by step solution

01

Analyze the integration ratios

The first piece of information we need to analyze is the integration ratios of the two signals in the 1H-NMR spectrum, presented as 6:1. This ratio indicates that there are six protons in the environment responsible for the doublet signal at δ 1.1 and one proton in the environment responsible for the septet at δ 3.6.
02

Analyze the chemical shifts and multiplicity of the signals

Next, we should determine the significance of the chemical shifts and the multiplicity of the signals. The doublet signal at δ 1.1 indicates the presence of adjacent protons. This chemical shift value is typical for alkyl protons adjacent to a carbon with no electron-withdrawing group. The septet at δ 3.6 suggests that the proton responsible for this signal is adjacent to six protons that are split into a septet. The chemical shift value at δ 3.6 is characteristic of a proton that is next to an oxygen atom.
03

Propose a structural formula for compound R

Considering the information obtained from Steps 1 and 2, along with the molecular formula C6H14O, the compound R must have an oxygen atom bonded to a carbon, which is subsequently bonded to a carbon chain with six protons. The only structure that fulfills these criteria is hexyl methoxy methane, as shown below: CH3-O-CH2-CH2-CH2-CH2-CH2-CH3 In this structure, the methoxy group (O-CH3) is responsible for the septet at δ 3.6, and the six alkyl protons (CH2-CH2-CH2-CH2-CH2) are responsible for the doublet at δ 1.1. Therefore, the structural formula for compound R, consistent with the given 1H-NMR data, is hexyl methoxy methane.

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Start your free trial

Over 30 million students worldwide already upgrade their learning with Vaia!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

Following is a \({ }^{1} \mathrm{H}\)-NMR spectrum of 2-butanol. Explain why the \(\mathrm{CH}_{2}\) protons appear as a complex multiplet rather than as a simple quintet.

When placed in a powerful magnetic field, there is a small population bias for the \({ }^{1} \mathrm{H}\) and \({ }^{13} \mathrm{C}\) nuclei to be aligned with the magnetic field, and they precess.

\({ }^{1}\) H-NMR signals are split because the spin state ( \(+\frac{1}{2}\) versus \(\left.-\frac{1}{2}\right)\) of nuclei of nonequivalent hydrogens no more than three bonds away influence the net magnetic field experienced by a given nucleus, an interaction known as spin-spin

Following is the \({ }^{1} \mathrm{H}\)-NMR spectrum of compound \(\mathrm{O}\), molecular formula \(\mathrm{C}_{7} \mathrm{H}_{12}\) Compound \(\mathrm{O}\) reacts with bromine in carbon tetrachloride to give a compound with the molecular formula \(\mathrm{C}_{7} \mathrm{H}_{12} \mathrm{Br}_{2}\). The \({ }^{13} \mathrm{C}-\mathrm{NMR}\) spectrum of compound \(\mathrm{O}\) shows signals at \(\delta 150.12,106.43,35.44,28.36\), and \(26.36\). Deduce the structural formula of compound \(\mathrm{O}\).

From the chemical shift of each signal, we derive information about the types of hydrogens in each set.
See all solutions

Recommended explanations on Chemistry Textbooks

The Earths Atmosphere

Read Explanation

Making Measurements

Read Explanation

Physical Chemistry

Read Explanation

Nuclear Chemistry

Read Explanation

Chemistry Branches

Read Explanation

Chemical Analysis

Read Explanation
View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.

Sign-up for free