1.
1 – counting the number of chemically non-identical carbons
2
1 3
4 Three carbons are chemically identical
Symmetrical molecule –
1
carbons are chemically identical
Only one signal!
1
2
3
4
5
6
1.2 – similar to carbon, just pay attention to the quaternary carbons (with four bonds) – there are no hydrogens!
Usually less signals.
1
2
2
1
1 3
3 4
5
2.1 – same as in the previous task. Answer is 2 (one -CH3 and one -CH2- groups)
2.2 – for -CH3 roughly at 1 ppm, slightly shifted to the left (because of Cl);
for -CH2- roughly at 3 ppm (~2-4 ppm), because of the influence of Cl atom.
2.3 – -CH3 will give triplet (because neighboring carbon has 2 hydrogen atoms.
Adding 1 equals 3)
-CH2- will give quadruplet (neighboring carbon has 3 hydrogen atoms.
Adding 1 equals 4)
2.4 – -CH3 will give integral of 3, -CH2- of 2
2.1 – 3 (one signal for two -CH3 groups; one for –CH< group, and one for –OH,
which can be removed from spectra with D 2O)
2.2 – for -CH3 roughly at 1 ppm, slightly shifted to the left (because of carbonyl);
for –CH< roughly at 3 ppm, because of the influence of carbonyl;
-OH from 10 to 12 ppm (if present)
2.3 – -CH3 will give doublet (because neighboring carbon has 1 hydrogen atoms.
Adding 1 equals 2)
-CH< will give septet (neighboring carbons have 6 hydrogen atoms in total.
Adding 1 equals 7)
-OH – singlet (if present)
2.4 – for –CH3 integral will be six (two groups); for –CH< one; for –OH also one.
To solve the problem, follow these steps:
CH3
?
1. Examine the formula – C7H8
There is only carbon and hydrogen, and clearly
some unsaturation (phenyl ring??)
2. Looking at 13C we see 5 signals (less than 7, some
symmetry??). One is aliphatic (21.5), and 4 are in
the aromatic range. Let‘s focus on aliphatic for now.
3. Look at the 1H. There are clearly aliphatic and
CH3
aromatic protons. Aliphatic – singlet with integral 3. It
can be only -CH3 group (which is also in agreement
with 13C signal at 21.5).
4. Looking further at 1H. There are 5 aromatic protons,
with some overlap. In combination with 4 aromatic
CH3 carbon signals in 13C, we can confirm that we have a
phenyl ring, which has one substituted proton.
5. As no unassigned signals are left, we can merge two
fragments into one, to give the final answer. CH3
6. Double check with formula – C7H8, and double check
the multiplets – all fit.
To solve the problem, follow these steps:
1. Examine the formula – C8H18O O
OH
There is oxygen. One way would be to quickly check
for possible oxygen functional groups.
A) There is no -OH (no broad signal in 1H,
exchangeable with D2O)
B) there is no carbonyl (>C=O) (no signal at >160
ppm in 13C)
2. Because of the electronegativity of O, we can expect
O
the signal at 70.7 in 13C NMR to be related to it.
From the table, we can suggest, that this is an ether.
H2 H2 H2
C C C
3. Look at the 1H. From integration we can see, that
there are three -CH2- groups, and one -CH3. Looking
O CH3
at the formula we can understand, that the mollecule
is symmetrical (so there will be double amount of
these groups).
H2
4. Looking further at 1H. Signal at ~3.4 should be C
O C
attached to oxygen (table). Because it is a triplet, it H2
is also connected to –CH2- group
H2 H2
5. Looking further at 1H. –CH3 group is also attached to C C
O C CH3
–CH2- (triplet). Now, the other two -CH2- signals are H2
split into 5 and 6 signals, showing us a connection
pattern.
O
6. Now we just need to double the molecule (as it is
symmetrical).
To solve the problem, follow these steps:
1. Examine the formula – C3H8O OH
There is oxygen, and there is a signal with a star at
CH3
1.6 ppm – this is –OH!
CH3
2. We have two more signals in H NMR. One has only
1
CH3 CH
one proton (>CH-), and one has six protons
CH
OH (two –CH3 groups?)
3. Let‘s check the multiplicity of the signals. –CH 3 is
doublet (neighbor has one proton), and >CH- is
septet (neighbors have six protons).
4. Additional piece of information - >CH- signal is
CH3 shifted to the left – so probably connected with O
atom.
OH
5. Now just put everything together!
CH
6. Double check with 13C NMR :)
