Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 18: Q19P (page 945)

Give the structures of the carbonyl compound and the amine used to form the following imines.

(a)

(b)

(c)

(d)

(e)

(f)

Short Answer

Expert verified

(a)

(b)

(c)

(d)

(e)

(f)

Step by step solution

01

Imines

Ammonia or primary amine under proper conditions reacts with a ketone or an aldehyde to form an imine.

02

Mechanism of imine formation

The mechanism of imine formation is a type of acid catalyzed nucleophlic addition of an amine to the carbonyl group.The fist step is the attack of an amine to an aldehyde or ketone which is followed by deprotonation of the nirogen atom that gives an unstable intermediate known as the carbinolamine. Second step is the conversion of carbinolamine to imine by loss of a water molecule. The formation of imine is a reversible process and most imines can be hydrolysed back into the amines and aldehydes or ketones.

03

Structures of carbonyl compound and the amine

(a)

(b)


(c)

(d)

(e)

(f)

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

Two structures for the sugar glucose are shown on page 950. Interconversion of the open-chain and cyclic hemiacetal forms is catalyzed by either acid or base.

(a) Propose a mechanism for the cyclization, assuming a trace of acid is present.

(b) The cyclic hemiacetal is more stable than the open-chain form, so very little of the open-chain form is present at equilibrium. Will an aqueous solution of glucose reduce Tollens reagent and give a positive Tollens test? Explain.

Name the following ketones and aldehydes. When possible, give both a common name and an IUPAC name.

(a)CH3CO(CH2)4CH3 (b)CH3(CH2)2CO(CH2)2CH3 (c)CH3(CH2)CO(CH2)2CH3

(d)PhCOPh (e)CH3CH2CH2CHO (f)CH3COCH3

(g)CH3CH2CHBrCH2CH(CH3)CHO (h)Ph-CH=CH-CHO

(i)CH3CH=CH-CH=CH-CHO

(j) (k) (l)

Propose a mechanism for the acid-catalyzed hydrolysis of cyclohexanone dimethyl acetal.

(a) Simple aminoacetals hydrolyze quickly and easily in dilute acid. Propose a mechanism for hydrolysis of the following aminoacetal:

(b) The nucleosides that make up DNA have heterocyclic rings linked to deoxyribose by an aminoacetal functional group. Point out the aminoacetal linkages in deoxycytidine and deoxyadenosine.

(c) The stability of our genetic code depends on the stability of DNA. We are fortunate that the aminoacetal linkages of DNA are not easily cleaved. Show why your mechanism for part (a) does not work so well with deoxycytidine and deoxyadenosine.

Like other strong nucleophiles, triphenylphosphine attacks and opens epoxides. The initial product (a betaine) quickly cyclizes to an oxaphosphetane that collapses alkene and triphenylphospine oxide.

  1. Show each step in the reaction of trans-2,3-epoxybutane with triphenylphospine to give but-2-ene. What is the stereochemistry of the double bond in the product?
  2. Show how this sequence might be used to convert cis-cyclooctene to trans-cyclooctene.
See all solutions

Recommended explanations on Chemistry Textbooks

Making Measurements

Read Explanation

Physical Chemistry

Read Explanation

Chemistry Branches

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Inorganic Chemistry

Read Explanation

Kinetics

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