Scribd
Upload
265 views6 pages

Problem set-III With Solutions PDF

The document provides information about NMR spectroscopy including: 1) Converting NMR absorption frequencies in Hz to chemical shifts in ppm units. 2) Chemical shifts indicate shielding, with higher ppm values being less shielded. 3) Multiple choice questions about NMR peak multiplicity and interpreting 1H NMR spectra. 4) Questions about atomic force microscopy resolution and advantages over electron microscopy. 5) Assigning infrared absorption bands to functional groups for 5 isomers of C5H10O.

Uploaded by

abhishek.ajmani
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
265 views6 pages

Problem set-III With Solutions PDF

The document provides information about NMR spectroscopy including: 1) Converting NMR absorption frequencies in Hz to chemical shifts in ppm units. 2) Chemical shifts indicate shielding, with higher ppm values being less shielded. 3) Multiple choice questions about NMR peak multiplicity and interpreting 1H NMR spectra. 4) Questions about atomic force microscopy resolution and advantages over electron microscopy. 5) Assigning infrared absorption bands to functional groups for 5 isomers of C5H10O.

Uploaded by

abhishek.ajmani
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
You are on page 1/ 6

BT501: Problem set-III

1. NMR absorptions were obtained on a spectrometer operating at 200 MHz and are given
in hertz downfield from the TMS standard. Convert the absorptions to units
a. 436 Hz
b. 956 Hz
c. 1504 Hz
Ans:
Chemical shift, (ppm) =

, The values given above are

. The reference

frequency,

= 200 MHz. Therefore, the chemical shifts in units i.e. in ppm are:

a. 436 Hz
b. 956 Hz
c. 1504 Hz

=
=
=

2.18 ppm
4.78 ppm
7.52 ppm

2. Is a nucleus that absorbs at 5.5 more shielded or less shielded than a nucleus that
absorbs at 3.2 ? Does the nucleus that absorbs at 5.5 require a stronger applied field
or a weaker applied field to come into resonance than the nucleus that absorbs at 3.2 ?
Ans:
The nucleus that absorbs 5.5 is less shielded than a nucleus that absorbs at 3.2 .
Consequently, the nucleus that absorbs at 5.5 requires a a weaker applied field to come
into resonance than the nucleus that absorbs at 3.2 .
3. What is the multiplicity of the hydrogen type shown in bold? (Hint: Tell if the peak
arising from these protons will be singlet, doublet, triplet, etc.)

Ans:
The protons shown in bold are equivalent; we therefore have only one proton type in
question. The adjacent carbon is having only one proton attached to it. Therefore, by n+1
rule, the multiplicity of the protons shown in bold is doublet.
4. What is the multiplicity of the hydrogen type shown in bold? Assume that the CH 2 is
significantly different from the CH3.

a) Singlet
1

b)
c)
d)
e)

Doublet
Quartet
4 3 peaks
7 3 peaks

5. What is the multiplicity of the hydrogen type shown in bold?

Ans: Doublet
6. What is the multiplicity of the hydrogen type shown in bold?

Ans: Singlet
7. Refer to the 1D proton NMR spectrum shown below for a compound with formula
C3H7Br. Answer the questions asked below.

a) How many types of hydrogen are present, assuming no serious overlap


between different types?
Three
b) What is the chemical shift of the hydrogen type that is most upfield? Give
approximate values or range.
~ 1 Hz

c) What best describes the most upfield hydrogen type?


i.
Singlet
ii. Doublet
iii. Triplet
iv.
Quartet
v.
Doublet of doublets
d) What does this multiplicity indicate about the most upfield hydrogens?
i.
There is one hydrogen present at this position
ii. There are two hydrogens present at this position
iii. There are three hydrogens present at this position
iv.
There are two hydrogens on the neighbouring carbon
v.
There are three hydrogens on the neighbouring carbon
e) What does the integration show about the most upfield hydrogens?
i.
There is one hydrogen present at this position
ii. There are two hydrogens present at this position
iii. There are three hydrogens present at this position
iv.
There are two hydrogens on the neighbouring carbon
v.
There are three hydrogens on the neighbouring carbon
f) What can you conclude about the most upfield hydrogens, using the above
evidence?
i.
They represent a CH2 group, attached to another CH2.
ii. They represent a CH2 group, attached to a CH3.
iii. They represent a CH3 group, attached to a CH2.
iv.
They represent a CH3 group, attached to another CH3.
v.
They represent a CH2 group, attached to CH.
g) What is the chemical shift of the hydrogen type that is most downfield? Give
approximate values or range.
~3.4 Hz
h) Knowing that the formula for this compound is C3H7Br, what does the
chemical shift of these downfield hydrogens suggest?
i.
ii.
iii.
iv.

There is an aromatic ring attached at this position


There is a bromine attached at this position
The aromatic ring is at the other end of the molecule
The bromine is at the other end of the molecule

i) How many hydrogens are present at this downfield position?

Two

j) How many hydrogens are present on the carbon adjacent to the downfield
position?
Two
8. Resolution in atomic force microscopy is limited by probe geometry and diameter
while that of light microscopy is limited by wavelength of the light used .
9. The resolution of an atomic microscope is highest in
z).

dimension (x, y, or,

10. Which mode of an atomic force microscope can be used for obtaining the high
resolution frictional coefficient profile of a surface?
a. Contact mode
b. Intermittent contact mode
c. Non-contact mode
11. Infrared spectroscopy provides valuable information about
a. Molecular weight
b. Functional groups
c. Conjugation
d. Melting point
12. Mention any two advantages of AFM over EM.
Ans:
i. AFM can be used for imaging the samples in solution while EM cannot.
ii. AFM does not require any staining of the specimen while EM usually does require
staining with heavy metals

13. Match the five C5H10O isomers below with the key infrared absorption bands listed:
(Note: the fingerprint bands and alkane C-H stretches are not reported.)
Refer to table 1 on Page 5 for typical vibrational wavenumbers of key functional groups
and the guidelines for identifying the functional groups.

Absorption band(s)

Molecule

3400 cm-1
3400, 1660 cm-1
1715 cm-1
1660, 1100 cm-1

1100 cm-1

14. One of the five compounds shown below was analyzed by infrared spectroscopy. Peaks
were observed at: 1639 cm-1 (weak) and 1714 cm-1 (strong) but were absent at 32003400 cm-1. Which compound was analyzed?

Ans:
i. A strong peak at 1714 cm-1 is suggestive of carbonyl group. Therefore compounds
A, B, and D are ruled out.
ii. Absence of any peak in the region 3200 3400 cm-1 suggests absence of hydroxyl
group. This further rules out compound A and D.
iii. Presence of a weak band at 1639 cm-1 could arise from an alkene. Therefore, the
compound analyzed was E.

Table 1: Typical vibrational wavenumbers of key functional group


Wavenumber

Vibration Functional groups

3500 3250
3500 3200

NH
OH

3100 3000

CH

3000 2850
1760 1665
1680 1640
1000 1260

CH
C=O
C=C
CO

Remarks

Amine
Alcohols
Alkenes
Aromatics
Alkanes
Ketone, Aldehyde, Ester, etc.
Alkene
Alcohol, Ether, Ester, Acid

Medium
Strong, Broad
Medium
Strong
Strong
Strong
Medium/Weak
Strong

General guidelines for identifying the functional groups (Not to be taken as rules):
i.
ii.

Begin by looking in the region from 4000-1300.


Look at the CH stretching bands around 3000:
a. Are any or all bands lesser than but close to 3000
b. Are any or all bands higher than but close to 3000

Alkyl group
C=C bond/aromatic group

iii.

Look for a carbonyl in the region 1760-1665. If there is such a band:


a. Is an OH band also present?
Carboxylic acid
b. Is a CO band also present?
Ester
c. Is an aldehydic CH band (28302695) also present?
Aldehyde
d. Is an NH band also present?
Amide
e. Are none of the above present?
Ketone

iv.

Look for a broad OH band in the region 3500-3200 cm-1 Alcohol/phenol

v.

Look for a single or double sharp NH band in the region 3500-3250 cm-1. If there is
such a band:
a. Are there two bands?

A primary amine
b. Is there only one band?

A secondary amine

You might also like