Solution Found!

A compound with molecular formula C10H10O4 exhibits only

Chapter 21, Problem 21.77

(choose chapter or problem)

Get Unlimited Answers
QUESTION:

A compound with molecular formula C10H10O4 exhibits only two signals in its 1 H NMR spectrum: a singlet at 4.0 (I = 3H) and a singlet at 8.1 (I = 2H). Identify the structure of this compound.

Questions & Answers

QUESTION:

A compound with molecular formula C10H10O4 exhibits only two signals in its 1 H NMR spectrum: a singlet at 4.0 (I = 3H) and a singlet at 8.1 (I = 2H). Identify the structure of this compound.

ANSWER:

Step 1 of 2

First, notice that the molecular formula C10H10O4 indicates the hydrogen deficiency index of six. With only ten carbons in the molecule, this means we almost we almost certainly have benzene present; it would account for four elements of unsaturation (3 double bonds, 1 ring). That leaves two double bonds rings left.

The singlet at 8.1 ppm (worth four protons) is characteristic of a para disubstituted benzene with a mirror plane of symmetry. The chemical shift of the aromatic ring (slightly downfield of a typical benzene) indicates that there are electron-withdrawing groups attached to the 1,4 positions on the benzene. Carbonyl groups fit this description, and we know that we have two elements of unsaturation left. Placing a carbonyl group on the 1,4 positions of the benzene ring would leave us with two carbons, two oxygens, and six hydrogens left in the molecular formula.

Add to cart


Study Tools You Might Need

Not The Solution You Need? Search for Your Answer Here:

×

Login

Login or Sign up for access to all of our study tools and educational content!

Forgot password?
Register Now

×

Register

Sign up for access to all content on our site!

Or login if you already have an account

×

Reset password

If you have an active account we’ll send you an e-mail for password recovery

Or login if you have your password back