/*! 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} Q. 2.77 Which H atom in vitamin C (ascor... [FREE SOLUTION] | 91影视

91影视

Log out

Learning Materials

Features

Discover

Chapter 2: Q. 2.77 (page 90)

Which H atom in vitamin C (ascorbic acid) is most acidic?

Short Answer

Expert verified

The most acidic proton gives more resonance stabilization through the delocalization of stable carbanion.

Step by step solution

01

Acidic proton

The most acidic proton gives more resonance stabilization through the delocalization of stable carbanion.

02

Delocalization of carbanion

A carbanion (bearing a negative charge) formed by the abstraction of an acidic proton transfers its electrons to the adjacent empty orbital (delocalization) and forms resonance structures.

The more the resonance structures, the more is the stability of the compound.

Therefore, the compound readily releases its proton to get stabilized by the resonance.

03

Explanation

The OH bonded with the alkene undergoes delocalization and forms three resonance stabilized structures through carbanion's formation after the proton's abstraction.

Therefore, this OH group has the most acidic hydrogen.

Formation of resonance structures

The other three -OH groups show their resonance stabilized structures as

Formation of resonance structures

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 91影视!

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

Atenolol is a 尾(beta) blocker, a drug used to treat high blood pressure. Which of the indicated N-H bonds is more acidic? Explain your reasoning.

Classify each reaction as either a proton transfer reaction, or a reaction of a nucleophile with an electrophile. Use curved arrows to show how the electron pairs move.

DBU, 1,8-diazabicyclo[5.4.0] undec-7-ene, is a base we will encounter in elimination reactions in Chapter 8. Which N atom is more basic in DBU? Explain your choice.

Answer the following questions about esmolol, a drug used to treat high blood pressure sold under the trade name Brevibloc.

a. Label the most acidic hydrogen atom

b. What products are formed when esmolol is treated with NaH?

c. What products are formed when esmolol is treated with HCl?

d. Label allsp2 hybridized C atoms. in esmolol.

e. Label the only trigonal pyramidal atom.

f. Label all C鈥檚 that bear a未+ charge.

Acetonitrile (CH3CN) has a pKaof 25, making it more acidic than many other compounds having only C-H bonds. Draw Lewis structures for acetonitrile and its conjugate base. Use resonance structures to account for the acidity of acetonitrile.
See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Reactions

Read Explanation

The Earths Atmosphere

Read Explanation

Chemical Analysis

Read Explanation

Nuclear Chemistry

Read Explanation

Kinetics

Read Explanation

Inorganic 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.