Molecular Formula (Chemical Formula)

Calculate degrees of unsaturation

Look at types of atoms

Think about possible functional groups

Contains oxygen Does not contain oxygen

If degrees of freedom, think carbonyl group If < 4 degrees of freedom, think alkene or alkyne
If no degrees of freedom, think alcohol or ether If > 4 degrees of freedom, think benzene

Halogens

Treat halogens as if
there were hydrogens
ex. C22H55Cl = C33H66
 Singlet Doublet

- No neighboring (adjacent) hydrogens - One neighboring (adjacent) hydrogen

H R H O H H
H C C R H C C R H C C R
H R H H R

Triplet Quartet

- Two neighboring (adjacent) hydrogens - Three neighboring (adjacent) hydrogens

H H H H
H C C R R C C H
H H H H

H = Hydrogens that we are interseted in

H = Hydrogens that we use for the n+1 rule

Note: the number of lines in the peak does not refer to the number of hydrogens; a singlet does not mean 1
hydrogen; a double does not mean 2 hydrogens
 Triplet

H H
All three are
H C C R
equivalent
H H

- Pick a specific carbon with hydrogens

- Look at adjacent carbon(s) and count the number of hydrogens...then add 1
- The n + 1 value refers to the peak arising from the carbon with hydrogens you picked

n + 1 = 2 + 1 = 3 (triplet)

In this case, the triplet refers to signal (peak) from the three red hydrogens
We
We have
have 1°
1° of
of unsaturation
unsaturation and
and oxygens:
oxygens: carbonyl
carbonyl

O
O

R
R R
R

We
We have
have aa quartet
quartet at
at ~~ 44 ppm:
ppm: these
these hydrogens
hydrogens must
must be
be next
next to
to 33 hydrogens
hydrogens

H
H H
H
R
R C
C C
C H
H
H
H H
H

We
We have
have aa singlet
singlet at
at ~~ 22 ppm:
ppm: these
these hydrogens
hydrogens are
are not
not next
next to
to any
any hydrogens
hydrogens

H R
H R H
H O
O
H C
H C C
C R
R H
H C
C C
C R
R
H R
H R H
H

We have
We have aa triplet
triplet at
at ~~ 11 ppm:
ppm: these
these hydrogens
hydrogens must
must be
be next
next to
to 22 hydrogens
hydrogens

H
H H
H
H
H C
C C
C R
R
H
H H
H
 O
O

R
R R
R

H H
H H H H
H H H O
H O
H C
H C C
C R
R R C
R C C
C H
H H C
H C C
C R
R
H H
H H H H
H H H
H

Where does
Where does the
the extra
extra oxygen
oxygen go?
go? Let's
Let's look
look at
at our
our NMR
NMR charts:
charts:

H
H
R C
R C OR
OR
R
R
H == 3-4
H 3-4 ppm
ppm

Therefore, we
Therefore, we must
must have:
have:

H
H H
H H H
H H H H
H H
RO C
RO C C H
C H RO C
RO C C
C H
H RO C
RO C C C H
H
H
H H
H H H
H H H11 H
H H

gives rise
gives rise to
to 44 ppm
ppm shift
shift quartet (n+1)
quartet (n+1) triplet (n+1)
triplet (n+1)

Now, we
Now, we have
have used
used 22 carbons,
carbons, 55 hydrogens,
hydrogens, and
and one
one oxygen.
oxygen. All
All we
we have
have left
left to
to figure
figure out
out
is the
is the remaining
remaining 22 carbons,
carbons, 33 hydrogens,
hydrogens, and
and 11 oxygen.
oxygen. After
After our
our analysis,
analysis, we
we know
know wewe have
have aa carbonyl
carbonyl and
and
aa singlet
singlet peak
peak at
at 22 ppm.
ppm. Let's
Let's see
see how
how to
to put
put this
this together:
together:

H O
H O H H
H H
H C
H C C
C C C
C C H
H
H
H H H
H H
(from above)
(from above)

singlet (n+1)
singlet (n+1)

H O
H O H H
H H
H C
H C C
C O
O C
C C
C H
H
H
H H H
H H