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Chapter 2: 2.27 (page 78)

Which anion (A or B) is the stronger base?

Short Answer

Expert verified

B is the stronger base.

Step by step solution

01

Determination of strong organic bases

In organic chemistry, strong bases are determined based on the free lone pair of electrons.

If the adjacent lone pair of electrons does not undergo delocalization, the compound is a strong base.

02

Effect of lone pairs on basicity

In compound A, the oxide ion containing the lone pair of electrons shifts towards the electron-deficient carbonyl carbon (C=O). Due to this, the delocalization of lone pair of electrons on an oxygen atom occurs. Hence, A is not a strong base.

Conjugation of an oxide ion

In compound B, the oxide ion-containing lone pair of electrons are free to donate. Its electron-donating tendency is further enhanced by the cyclohexyl group. Hence, B is a strong base.

Therefore, B is a stronger base than A.

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Most popular questions from this chapter

Many drugs are Brønsted-Lowry acids or bases.

a. What is the most acidic proton in the analgesic ibuprofen? Draw the conjugate base.

b. What is the most basic electron pair in cocaine? Draw the conjugate acid.

a. Which compounds are Brønsted-Lowry acids: HBr,NH3,CCl4?

b.Which compounds are Brønsted-Lowry bases:CH3CH3,(CH3)3CO-,HC≡CH?

c. Classify each compound as an acid, a base, or both: CH3CH2OH,CH3CH2CH2CH3,CH3CO2CH3

Rank the compounds in each group in order of increasing acidity.

a.

b.

c.

Draw the products of each proton transfer reaction. Label the acid and base in the starting materials, and the conjugate acid and base in the products.

a.

b.

c.

d.

Write a stepwise reaction sequence using proton transfer reactions to show how the following reaction occurs. (Hint: As a first step, useOH- to remove a proton from theCH2 group between the C=O and C=C.)
See all solutions

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