Problem : C = 59.96%, H = 13.42.

SOLUTION
In the MS, the molecular ion occurs at m/z = 60 indicating the MW = 60 g/ mol.
The IR shows an -OH (3350 cm-1) and C-O (1075 cm-1) but no C=O (around 1700 cm-1), or C=C (around
1600 cm-1)

13

H-nmr

C-nmr shows 3 types of C, including a deshielded C (69 ppm), and 2 other hydrocarbon C (27 and 10
ppm)

/ppm

multiplicity

integration

assignment

3.6

triplet

CH2 coupled to 2H, deshielded

2.3

singlet

isolated H (-OH ?)

1.6

multiplet

CH2 coupled to many H

0.9
triplet
3
CH3 coupled to 2H
The H-NMR gives us the following pieces -OH (helped by the IR) -CH3, and 2 different -CH2-.

We can start to fit them together based on the coupling patterns as: CH3CH2CH2-

Summary....
The MS indicated MW = 60 g/mol.
The IR showed the presence of an O-H and C-O bonds.

H nmr gives a CH3CH2CH2- group

From the data, we can get a molecular formula of C3H8O = 3 x 12 + 8 x 1 + 1 x 16 = 60 g/mol

This has an IHD = 0, so no bonds or rings.

Altogether....
With the pieces we have : CH3CH2CH2- and -OH
IR an consistent with an alcohol.
Given these pieces, there is only one way they can fit together.
Checking the H-nmr, the middle -CH2- is actually six lines since it has
a total of 5 similar neighbours. The -OH deshields the other -CH2- but
does not couple to it.

Problem : C = 54.53%, H = 9.15%, O = 36.32%

1-propanol

SOLUTION
In the MS, the molecular ion occurs at m/z = 88 indicating the MW = 88 g/mol (even, no isotope pattern
for Cl or Br)
The IR shows a carbonyl C=O (1740 cm-1), and possible C-O (between 1250-1000 cm-1). No -OH or -NH
(above 3200 cm-1).

13 C-nmr shows 4 peaks indicating 6 types of C, a C=O (171 ppm, probably an acid derivative), a C-O at
60 ppm and 2 hydrocarbon C (21 and 14 ppm)

H-nmr

/ppm

multiplicity

integration

4.1

quartet

CH2 coupled to 3H, deshielded by O ?

2.0

singlet

CH3 with no adjacent H, slightly deshielded

assignment

1.3
triplet
3
CH3 coupled to 2H
The most significant structural information in the H nmr data is that we have an ethyl group : -CH2CH3 most likely as an ethoxy group: -O-CH2-CH3 and an isolated methyl group : -CH3

Summary....
The MS indicated MW = 88 g/mol.
The IR showed the presence of C=O and C-O bonds, possibly an ester

13C peak at 171 ppm suggests that the C=O is a carboxylic acid derivative, an ester ?

H nmr also gives a -O-CH2-CH3 and an uncoupled -CH3.

Use this to check the molecular formula : C4H8O2 = 4 x 12 + 8 x 1 + 2 x 16 = 88 g/mol

So with all this information we have the following pieces: C=O, -O-CH2-CH3, and -CH3.

Altogether....

With the pieces we have : C=O, -O-CH2-CH3, and -CH3.

IR and 13C suggest an ester so we have : CO2CH2-CH3
This only leaves the -CH3 group.
Therefore, it must be CH3-CO2CH2-CH3

Problem : C = 29.30%, H = 5.74%, Br = 64.97%.

ethyl ethanoate
or
ethyl acetate

SOLUTION
In the MS, the pair of peaks of about 1:1 ratio at 122 and 124 suggest Br due to the isotopes79Br and 81Br
The molecular ion occurs at m/z = 122 indicating the MW = 122 g / mol (based on 79Br)

The IR shows has no absorbtions for the main functional groups, looks like C-H and C-C only.

13 C-nmr shows 3 types of C, including a slightly deshielded C (35 ppm) plus 2 other hydrocarbon C (26
and 13 ppm)

H-nmr
/ppm

multiplicity

integration

assignment

3.4

triplet

CH2 deshielded, coupled to 2H

1.8

sextet

CH2 coupled to 5H

1.0

triplet

CH3 coupled to 2H

Summary....
The MS indicated MW = 122 g/mol.
The H nmr gives a total of 7 H, C nmr 3 C

Use this to check the molecular formula : C3H7Br = 3 x 12 + 7 x 1 + 1 x 79 = 122 g/mol

This confirms that we have the molecular formula

Altogether....
The coupling patterns in the H nmr are the critical information
The patterns give a CH3 next to a CH2 and a CH2 next to
another CH2
Since we only have 3C, this means we have a CH3CH2CH2With the pieces we have : CH3CH2CH2- and -Br
This can only be put together to give CH3CH2CH2-Br

1-bromopropane

Problem

: C = 56.24%, H = 6.29%.

Homo-COSY

Hetero-COSY

Problem : A compound contains C =69.72%, H = 11.70% of elemental composition. The UV spectrum of this
compound is determined in 95% ethanol: max 280 nm (log 1.3).

Problem : A compound contains C = 48.64%, H =8.16% of elemental composition. The UV spectrum of this
compound shows no maximum above 205 nm. A peak at 161 ppm appears as a positive peak in the DEPT-90
spectrum.

Problem : A compound contains C = 53.98%, H = 6.04%, S = 16.01% of elemental composition. The UV

spectrum of this compound is determined in 95% ethanol: max 225 nm (log 4.0) and 270 nm (log 2.8).

Problem : A compound contains C = 36.95%, H = 5.68% and Br = 40.96% of elemental composition. The
13
C-NMR spectrum shows peaks at 14.0, 31.0, 56.1, 62.0, and 172.2 ppm.

Problem :

C = 62.68%, H = 4.51%, N = 20.88%