/*! This file is auto-generated */ .wp-block-button__link{color:#fff;background-color:#32373c;border-radius:9999px;box-shadow:none;text-decoration:none;padding:calc(.667em + 2px) calc(1.333em + 2px);font-size:1.125em}.wp-block-file__button{background:#32373c;color:#fff;text-decoration:none} Q13-27E Question: How many electronicall... [FREE SOLUTION] | 91Ó°ÊÓ

91Ó°ÊÓ

Question: How many electronically non-equivalent kinds of protons and how

many kinds of carbons are present in the following compound? Don’t

forget that cyclohexane rings can ring-flip.

Short Answer

Expert verified

If you assign R, S configuration to the carbons bonded to methyl group, it is apparent that cis-1,2-dimethylcyclohexane is a mesocompound. When the cyclohexane ring undergoes a ring-flip, the ring passes through an intermediate that has a plane of symmetry. Both the13C NMR spectrum and the1H NMR spectrum show 4 peaks.

Step by step solution

01

Step 1: 1H NMR and 13C NMR spectroscopy

NMR stands for Nuclear Magnetic Resonance Spectroscopy. This is the technique used for determining the structure of the organic compounds. It is a non-destructive technique. It is of two types1H NMR and13C NMR.

Proton nuclear magnetic resonance (1H NMR) is the application of nuclear magnetic resonance in NMR spectroscopy with respect to hydrogen-1 nuclei within in the molecule of substance in order to determine the structure of its molecules.

Carbon-13 nuclear magnetic resonance is the application of nuclear magnetic resonance spectroscopy to carbon. It is analogous to proton NMR and allows the identification of carbon atom in an organic molecule just as proton NMR identifies Hydrogen atoms.

02

Chemically equivalent and Non-equivalent protons

In the terms of NMR,all three Ha protons are chemically equivalent to each other, as are all three Hb protons. The Ha protons are, however, chemically non-equivalent to the Hb protons. As a result, the resonance frequency of the Ha protons is different from that of the Hb protons. For example methyl acetate has two distinct set of protons.
The three methyl acetate protons labelled Ha below have different resonant frequency compared to three Hb protons, because the two sets of protons are in non-identical electronic environment.

03

Identify the kind of proton

If you assign R, S configuration to the carbons bonded to methyl group, it is apparent that cis-1,2-dimethylcyclohexane is a mesocompound. When the cyclohexane ring undergoes a ring-flip, the ring passes through an intermediate that has a plane of symmetry.

Plane of symmetry in cyclohexane


Types of protons


Both the 13C NMR spectrum and the 1H NMR spectrum show 4 peaks.

Both the13C NMR spectrum and the1H NMR spectrum show 4 peaks.

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.

Over 30 million students worldwide already upgrade their learning with 91Ó°ÊÓ!

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

How could you use 1H NMR to determine the regiochemistry of electrophilic addition to alkenes? For example, does addition of HCl to 1-methylcyclohexene yield 1-chloro-1-methylcyclohexane or 1-chloro-2-methylcyclohexane?

Compound A, a hydrocarbon with M+= 96 in its mass spectrum, has theC13 spectral data given below. On reaction withBH3 , followed by treatment with basic H2O2, A is converted into B, whoseC13 spectral data are also given below. Propose structures for A and B.

Compound A Broadband-decoupledC13 NMR: 26.8, 28.7, 35.7, 106.9, 149.7 d DEPT-90: no peaks DEPT-135: no positive peaks; negative peaks at 26.8, 28.7, 35.7, 106.9 d

Compound B Broadband-decoupledC13 NMR: 26.1, 26.9, 29.9, 40.5, 68.2 d DEPT-90: 40.5 d DEPT-135: positive peak at 40.5 d; negative peaks at 26.1, 26.9, 29.9, 68.2 d

Propose a structure for compound C, which has M+= 86 in its mass spectrum, an IR absorption at 3400cm-1, and the following C13NMR spectral data:

Compound C Broadband-decoupled C13 NMR: 30.2, 31.9, 61.8, 114.7, 138.4 d DEPT-90: 138.4 d DEPT-135: positive peak at 138.4 d; negative peaks at 30.2, 31.9, 61.8, 114.7 d

The proton NMR spectrum is shown for a compound with the formula C5H9NO4. The infrared spectrum displays strong bands at 1750 cm-and 1562 cm-and a medium-intensity band at 1320 cm-. The normal carbon-13 and the DEPT experimental results are tabulated. Draw the structure of this compound.

Propose structures for compounds that fit the following NMR data:

(a) C5H10O

0.95δ(6H,double, J = 7Hz)

2.10δ(3H,singlet)

2.43δ(1H, mutiplet)

(b) C3H5Br

2.32δ(3H,singlet)

5.35 δ(3H,singlet)

5.45δ(1H, broad signet )

See all solutions

Recommended explanations on Chemistry Textbooks

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.