Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 14: Q8P (page 527)

Question: For each compound, which of the protons on the highlighted carbons absorbs farther downfield?

a.

b.

c.

Short Answer

Expert verified

  1. Blue proton will absorb downfield.

  2. Pink proton will absorb downfield.

  3. Blue proton will absorb downfield.

Step by step solution

01

Effect of electronegative atom on proton NMR

When an electronegative atom is attached to the\({\bf{C}}{{\bf{H}}_{\bf{2}}}\)group, the proton near it absorbs downfield.

02

Step 2: \(^{\bf{1}}{\bf{H}}\) NMR signals in a, b and c

a. F and Cl electronegative atoms are present in the given compound. Cl is less electronegative than F. The \({\rm{C}}{{\rm{H}}_{\rm{2}}}\) group adjacent to Cl is less deshielded, and its protons absorb upfield.

Thus, the\({\rm{C}}{{\rm{H}}_{\rm{2}}}\)group adjacent to F absorbs downfield.

b. The\({\rm{C}}{{\rm{H}}_{\rm{2}}}\)group adjacent to the electronegative oxygen atom absorbs downfield instead of the\({\rm{C}}{{\rm{H}}_2}\)group far away from the electronegative atom.

c. The \({\rm{C}}{{\rm{H}}_{\rm{2}}}\) group adjacent to the electronegative oxygen atom absorbs downfield instead of the \({\rm{C}}{{\rm{H}}_{\rm{3}}}\) group.

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

Question:Reaction of unknown A with HCl forms chlorohydrin B as the major product. A shows no absorptions in its IR spectrum at 1700 cm-1 or 3600-3200 cm-1 , and gives the following 1H NMR data: 1.4 (doublet, 3 H), 3.0 (quartet of doublets, 1 H), 3.5 (doublet, 1 H), 3.8 (singlet, 3 H), 6.9 (doublet, 2 H), and 7.2 (doublet, 2 H) ppm.

(a) Propose a structure for A, including stereochemistry.

(b) Explain why B is the major product in this reaction.

Question: How can you use 1H NMR spectroscopy to distinguish between CH2=C(Br)CO2CH3 and methyl (E)-3-bromopropenoate, BrCH=CHCO2CH3?

For each compound, first label each different type of proton and then rank the protons in order of increasing chemical shift.

a.

b.

c.

Into how many peaks will each proton shown in green be split?

a.

b.

c.

d.

e.

f.

Question: Draw the four constitutional isomers having molecular formula C4H9Brand indicate how many different kinds of carbon atoms each has.
See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Reactions

Read Explanation

Kinetics

Read Explanation

Physical Chemistry

Read Explanation

The Earths Atmosphere

Read Explanation

Chemical Analysis

Read Explanation

Nuclear Chemistry

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