MYTUTOR SUBJECT ANSWERS

1941 views

Why is phenylamine a weaker organic base than ethylamine?

Phenylamine contains a phenyl group attached to the amine. Phenyl groups have a delocalised system of electrons as a result of p orbitals from the 6 adjacent carbon atoms overlapping and "merging" together to form a 9very stable) delocalised pi bond with 6 electrons. The lone pair of the nitrogen atom in the amine group is "drawn in" towards this delocalisation and this interaction makes the lone pair less available to bond to an incoming H+ ion. In comparison, ethylamine has no delocalisation in the molecule. In fact, there is actually a positive inductive effect contributed from the alkyl groups of the ethylamine which pushes the lone pair away from the N atom and makes the lone pair more available to bond to an H+ ion. The availability of a lone pair of electrons on a base determines its strength as it is these electrons that will "mop up" H+ ions in solution and hence increase pH towards more alkaline conditions. Therefore, phenylamine is a weaker base than ethylamine because its lone pair is less available.

Adam W. GCSE Biology tutor, GCSE Chemistry tutor, GCSE Maths tutor, A...

1 year ago

Answered by Adam, an A Level Chemistry tutor with MyTutor


Still stuck? Get one-to-one help from a personally interviewed subject specialist

87 SUBJECT SPECIALISTS

£36 /hr

Michal D.

Degree: Chemistry (Masters) - Oxford, Jesus College University

Subjects offered: Chemistry, -Personal Statements-+ 1 more

Chemistry
-Personal Statements-
-Oxbridge Preparation-

“A 2nd year Chemistry student at University of Oxford looking to help you with any problems with the subject. Chemistry may seem difficult to you. This is probably because you don't know WHY something works the way it works. You don't ...”

£22 /hr

Hannah W.

Degree: Biology (Bachelors) - Bristol University

Subjects offered: Chemistry, Music+ 5 more

Chemistry
Music
Maths
History
English Literature
English Language
Biology

“Hi I'm Hannah and I am a Biology student at Bristol University. I have always loved the sciences, especially Biology and Chemistry but I am also passionate aboutcreative subjects such as Music and English.  I completely understand how...”

£20 /hr

Sahil M.

Degree: Medicine (Bachelors) - Manchester University

Subjects offered: Chemistry, Spanish+ 3 more

Chemistry
Spanish
Maths
Biology
-Medical School Preparation-

“Hello! My name is Sahil and I am currently a medical student at the University of Manchester. I am really looking forward to tutoring you in Spanish, Chemistry, Biology or Maths as well as trying to help you during the difficult proce...”

About the author

Adam W.

Currently unavailable:

Degree: Molecular & Cellular Biochemistry (Masters) - Oxford, Oriel College University

Subjects offered: Chemistry, Science+ 4 more

Chemistry
Science
Maths
Extended Project Qualification
Biology
-Personal Statements-

“Hello! A warm welcome to all… My name is Adam and I am a biochemistry student at Oxford University. In brief, Biochemistry encompasses all things science but particularly requires a deep and thorough understanding of maths, organic ch...”

You may also like...

Posts by Adam

How do you go about differentiating a^x functions?

In terms of reaction mechanisms, what exactly is the rate-determining step?

To what extent do the structures and functions of DNA and RNA differ?

What is the structure and role of a chloroplast?

Other A Level Chemistry questions

Describe how you test for an aldehyde or ketone and distinguish between the two.

How do you answer a long answer question on how buffer systems work?

0.250 g of a hydrocarbon known to contain carbon, hydrogen and oxygen was subject to complete combustion and produced 0.3664 g of CO2 and 0.1500 g of H2O. What is the empirical formula of this hydrocarbon?

What is a mole and why is it useful?

View A Level Chemistry tutors

Cookies:

We use cookies to improve our service. By continuing to use this website, we'll assume that you're OK with this. Dismiss

mtw:mercury1:status:ok