Question: Draw the structure of a 1°,2°,3°, , carbocation, each having molecular formula . Rank the three carbocations in order of increasing stability.

Short Answer

Expert verified

Answer

The structure of 1°,2°,3°and carbocations, each having the molecular formula is provided below.

The carbocations can be ranked in the order of increasing stability as follows:

Step by step solution

01

Carbocations

Carbocations are “electron-deficient” species comprising a trigonal planar shape. Several factors provide stability to a carbocation, and one of them is the inductive effect.

02

Structures of 1°,2°,3° carbocations possessing the molecular formula C4H9+

The structures of 1°,2°,3°carbocations, comprising the molecular formula , can be given as:

Structure of various carbocations comprising the molecular formula

The alkyl groups exhibit a positive inductive effect by donating electron density, thereby stabilizing the electron-deficient carbon. Tertiary carbocations are highly stable because the electron-deficient carbon is linked to three alkyl groups.

03

Arrangement of carbocations in the increasing order of stability

The stability of a carbocation is based on various effects, such as the inductive effect and hyperconjugation. The carbocations can be arranged in the order of increasing stability as:

Arrangement of carbocations in the increasing order of stability

The alkyl groups exhibit a positive inductive effect by donating electron density, thereby stabilizing the electron-deficient carbon. Tertiary carbocations are highly stable because the electron-deficient carbon is linked to three alkyl groups.

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 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: When a single compound contains both a nucleophile and a leaving group, an intramolecular reaction may occur. With this in mind, draw the product of the following reaction.

Question: Quinapril (trade name Accupril) is used to treat high blood pressure and congestive heart failure. One step in the synthesis of quinapril involves the reaction of the racemic alkyl bromide A with a single enantiomer of the amino ester B. (a) What two products are formed in this reaction? (b) Given the structure of quinapril, which one of these two products is needed to synthesize the drug?

quinapril

Question: As you will learn in Chapter 9, the epoxide is an ether with an oxygen atom in a three-membered ring. Epoxides can be made by intramolecular SN2 reactions of intermediates that contain a nucleophile and a leaving group on adjacent carbons, as shown.

Assume that each of the following starting materials can be converted to an epoxide by this reaction. Draw the product formed (including stereochemistry) from each starting material. Why might some of these reactions be more difficult than others in yielding nucleophilic substitution products?

a.

b.

c.

d.

Question: Which of the following molecules contain a good leaving group?

a.

b.

c.

d.

Question: Draw the eight constitutional isomers having the molecular formula C5H11Cl .

  1. Give the IUPAC name for each compound (ignoring R and S designations).
  2. Classify each alkyl halide as 1°,2°or3°.
  3. Label any stereogenic centers.
  4. For each constitutional isomer that contains a stereogenic center, draw all possible stereoisomers, and label each stereogenic center as R or S.
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.

Sign-up for free