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Interpreting IR Specta - A Quick Guide - Master Organic Chemistry
Interpreting IR Specta - A Quick Guide - Master Organic Chemistry
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Organic LOGIN
Chemistry
Last post, we briefly introduced the concept of bond vibrations, and we saw that we can think of
covalent bonds as a bit like balls and springs: the springs vibrate, and each one “sings” at a
characteristic frequency, which depends on the strength of the bond and on the masses of the
atoms. These vibrations have frequencies that are in the mid-infrared (IR) region of the
electromagnetic spectrum.
We can observe and measure this “singing” of bonds by applying IR radiation to a sample and
measuring the frequencies at which the radiation is absorbed. The result is a technique known as
Infrared Spectroscopy, which is a useful and quick tool for identifying the bonds present in a
given molecule.
We saw that the IR spectrum of water was pretty simple – but moving on to a relatively complex
molecule like glucose (below) we were suddenly confronted with a forest of peaks!
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Your first impression of looking at that IR might be: agh! how am I supposed to make sense of
that??
tryingMaster
to squeeze every last bit of information out of the spectrum. Today, with access to
NMR Organic
and other techniques, we can do more cherry-picking]
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We don’t need to analyze every single peak ! (as we’ll see later, that’s what NMR is for :
– ) ). Instead, IR is great for identifying certain specific functional groups, like
alcohols and carbonyls. In this way it’s complimentary to other techniques (like NMR) which
don’t yield this information as quickly.
With this in mind, we can simplify the analysis of an IR spectrum by cutting out everything
except the lowest-lying fruit.
See that forest of peaks from 500-1400 cm-1 ? We’re basically going to ignore them all!
80% of the most useful information for our purposes can be obtained by looking at two specific
areas of the spectrum: 3200-3400 cm-1 and 1650-1800 cm-1. We’ll also see that there are at
least two more regions of an IR spectrum worth glancing at, and thus conclude a “first-order”
analysis of the IR spectrum of an unknown. [We might write a subsequent post which gets nittier
and grittier about the finer points of analyzing an IR spectrum]
Bottom line: The purpose of this post is to show you how to prioritize your time in an analysis of
an IR spectrum.
[BTW: all spectra are from the NIST database. Thank you, American taxpayers!]
2. Starting With “Hunt And Peck” Is Not The Way To Go
Confronted with an IR spectrum of an unknown (and a sense of rising panic), what does a
typical new student do?
They often reach for the first tool they are given, which is a table of common ranges for IR peaks
given to them by their instructor.
The next step in their analysis is to go through the spectrum from one side to the next, trying to
match every single peak to one of the numbers in the table. I know this because this is exactly
what I did when I first learned IR. I call it “hunting and pecking”.
So by reading the next few paragraphs you can save yourself a lot of time and confusion.
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[Hunt and peck
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has its place, but only AFTER you’ve looked for “tongues” and “swords”, below.
Chemistry
Hunting and pecking is great to make sure you didn’t miss anything big – but as a first step, it’s
bloody awful!]
3. The Big Picture
In IR spectroscopy we measure where molecules absorb photons of IR radiation. The peaks
represent areas of the spectrum where specific bond vibrations occur. [for more background, see
the previous post, especially on the “ball and spring” model]. Just like springs of varying weights
vibrate at characteristic frequencies depending on mass and tension, so do bonds.
Here’s an overview of the IR window from 4000 cm -1 to 500 cm -1 with various regions of interest
highlighted.
Within these ranges, there are two high-priority areas to focus on, and two lesser-priority
areas we’ll discuss further below.
4. The Two Main Things To Look For In An IR Spectrum: “Tongues”
and “Swords”.
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When confronted with a new IR spectrum, prioritize your time by asking two important
questions: Organic
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1. Is there a broad, rounded peak in the region around 3400-3200 cm-1 ? That’s where
hydroxyl groups (OH) appear.
2. Is there a sharp, strong peak in the region around 1850-1630 cm-1 ? That’s where carbonyl
groups (C=O) show up.
First, let’s look at some examples of hydroxyl group peaks in the 3400 cm-1 to 3200 cm-1 region,
which Jon describes vividly as “tongues”. The peaks below all belong to alcohols. Hydrogen
bonding between hydroxyl groups leads to some variations in O-H bond strength, which results
in a range of vibrational energies. The variation results in the broad peaks observed.
Hydroxyl groups that are a part of carboxylic acids have an even broader appearance that we’ll
describe in a bit.
[Sometimes it helps to know what not to look for. On the far right hand side is included one
example of a very weak peak on a baseline that you can safely ignore.]
The main point is that a hydroxyl group isn’t generally something you need to go looking for in
the baseline noise.
Although hydroxyl groups are the most common type of broad peak in this region, N-H peaks
can show up in this area as well (more on them in the Note 1). They tend to have a sharper
appearance and may appear as one or two peaks depending on the number of N-H bonds.
Next, let’s look at some examples of C=O peaks, in the region around 1630-1800 cm-1.. These
peaks are almost always the strongest peaks in the entire spectrum and are relatively narrow,
giving them a somewhat “sword-like” appearance.
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That sums up our 80/20 analysis: look for tongues and swords.
If you learn nothing else from this post, learn to recognize these two types of peaks!
Two other regions of the IR spectrum can quickly yield useful information if you train yourself to
look for them.
3. The line at 3000 cm-1 is a useful “border” between alkene C–H (above 3000 cm-1) and alkane
C–H (below 3000 cm-1 ) This can quickly help you determine if double bonds are present.
4. A peak in the region around 2200 cm-1 – 2050 cm-1 is a subtle indicator of the presence of a
triple bond [C≡N or C≡C] . Nothing else shows up in this region.
A Common Sense Reminder
Let’s look at a specific example so we can see everything in perspective. The spectrum below is
of 1-hexanol.
Note the hydroxyl group peak around 3300 cm-1 , typical of an alcohol (That sharp peak around
3600 cm-1 is a common companion to hydroxyl peaks: it represents non-hydrogen bonded O-H).
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As you’d expect for 1-hexanol, there isn’t any telltale carbonyl peak around 1700 cm -1. Beginners
might be tempted
Organic to label that dagger-like strong peak
Master
at about 1450 cm-1 as a possible C=O
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stretch. It isChemistry
not. (it’s likely a C-H bend). Variations only occur within a very narrow range, and
you are extremely unlikely to see a C=O stretch much below 1650 cm-1. The more spectra you
see, the better you’ll get at making these judgements.
To gain some familiarity with variation, here’s some more examples of entire IR spectra of
various alcohols.
Phenol
Cyclohexanol
1-butanol
Carboxylic Acids
Hydroxyl groups in carboxylic acids are considerably broader than in alcohols. Jon calls it a
“hairy beard”, which is a perfect description. Their appearance is also highly variable. The OH
absorption in carboxylic acids can be so broad that it extends below 3000 cm-1 , pretty much
“taking over” the left hand part of the spectrum.
Here’s an example: butanoic acid.
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Here’s some more examples of full spectra so you can see the variation.
Benzoic acid,
Pentanoic acid,
Acetic acid
The difference in appearance between the OH of an alcohol and that of a carboxylic acid is
usually diagnostic. In the rare case where you aren’t sure whether the broad peak is due to the
OH of an alcohol or a carboxylic acid, one suggestion is to check the region around 1700 cm for
the C=O stretch. If it’s absent, you are likely looking at an alcohol.
[Note 1 for more detail on the 3200-3500 cm-1 region : Amines, Amides, and Terminal
Alkynes]
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The position of the C=O stretch varies slightly by carbonyl functional group. Some ranges (in
cm-1 ) are shown below:
Aldehydes (1740-1690): benzaldehyde, propanal, pentanal
Ketones (1750-1680): 2-pentanone, acetophenone
Esters (1750-1735): ethyl acetate, methyl benzoate
Carboxylic acids (1780-1710): benzoic acid, butanoic acid
Amide (1690-1630): acetamide, benzamide, N,N-dimethyl formamide (DMF)
Anhydrides (2 peaks; 1830-1800 and 1775-1740): acetic anhydride, benzoic anhydride
Conjugation will affect the position of the C=O stretch somewhat, moving it to lower
wavenumber.
A decent rule of thumb is that you will never, ever see a C=O stretch below 1630. If you see a
strong peak at 1500, for example, it is not C=O. It is something else.
7. Less Crucial, But Still Useful: Two More Very Diagnostic Areas.
1. The C-H Stretch Boundary at 3000 cm-1
3000 cm-1 serves as a useful dividing line. Above this line is observed higher frequency C-H
stretches we attribute to sp2 hybridized C-H bonds. Two examples below: 1-hexene (note the
peak that stands a little higher) and benzene.
For a molecule with only sp3-hybrized C-H bonds, the lines will appear below 3000 cm-1 as in
hexane, below.
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Molecules with triple bonds appear relatively infrequently in the grand scheme of things, but
when they do, they do have a distinctive trace in the IR.
The region between 2000 cm-1 and 2400 cm-1 is a bit of a “ghost town” in IR spectra; there’s
very little that appears in this region. If you do see peaks in this region, a likely candidate is a
triple bonded carbon such as an alkyne or nitrile.
Note how weak the alkyne peaks are. This is one exception to the rule that one should ignore
weak peaks. Still, caution is required: if you’re given the molecular formula, confirm that an
alkyne is possible by calculating the degrees of unsaturation and ensuring that it is at least 2 or
more.
Terminal alkynes (such as 1-hexyne) also have a strong C-H stretch around 3400 cm-1 that is
moreQuizzes,
strongly diagnostic.
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8. Glucose, Revisited: The a MOC
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A moleculeMaster
with one degree of hydrogen deficiency (C6H12O6) but no C=O, and likely no C=C ?
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A good guess would be that the molecule contains a ring. (We know this is the case, of course,
Organic
Chemistry
but it’s nice to see the IR confirming what we already know).
This is what a 1-minute analysis of the IR of glucose can tell us. Not the whole structure, mind
you, but certainly some important bits and pieces.
That’s enough for today. In the next post we’ll do some more 1-minute analyses and give more
concrete examples of how to use the information in an IR spectrum to draw conclusions about
molecular structure.
Notes
Related Articles
More on the 3200 region: Amines, Amides, and Terminal Alkyne C-H
Amines and amides also have N-H stretches which show up in this region. [update: a comment
from Paul Wenthold mentions some helpful advice about amides – they are rare – look for
confirming evidence from the mass spectrum or other sources before assigning an amide based
on a Quizzes,
stretch in this region, as Mechanisms
Reactions, this region can also
andcontain carbonyl
Summary “overtone”
Sheets (Orgpeaks]
1 + Org 2)
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Notice howMaster
the primary amine and primary amide have two “fangs”, while the secondary amine
and secondary
Organicamide have a single peak. LOGIN
Chemistry
The amine stretches tend to be sharper than the amide stretches; also the amides can be
distinguished by a strong C=O stretch (see below).
Primary amines (click for spectra)
Aniline
Benzylamine
Cyclohexylamine
Secondary amines:
N-methylbenzylamine
N,N-dibenzylamine
N-methylaniline
Primary amides
Propionamide
Benzamide
Butanamide
Secondary amides
N-methyl benzamide
Terminal alkyne C-H
Terminal alkynes have a characteristic C-H stretch around 3300 cm-1. Here it is for
ethynylbenzene, below.
Ethynylbenzene
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Comments
Masuzyo Sichimba
March 25, 2024 at 6:33 am
Ain’t this great! Man you’re an angel
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Aliasghar Behzadi
January 17, 2024 at 12:10 pm
this quick guide is awesome, I’ve learned so much reading it. To recall whatever
you forgot over time, this is the best option.
Thank you
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Cirona
November 15, 2023 at 3:29 am
This has really been helpful for my studies in chemistry
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James Ashenhurst
November 15, 2023 at 8:11 am
I am glad you find it helpful Cirona!
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Anand Vishwakarma
November 13, 2023 at 1:18 am
This is very helpful
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James Ashenhurst
November 14, 2023 at 9:38 pm
Glad you find it helpful Anand
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Bigdhaddy Andrew
August 2, 2023 at 2:39 am
I love this analysis very much impressive thanks 👍
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James Ashenhurst
August 2, 2023 at 9:06 am
Glad you find it helpful!
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Monica
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Rao LOGIN
June 20, 2023 at 11:42 pm
Chemistry
A lifesaver if there was ever one. Infrared Spectroscopy was so confusing for me in
undergrad,and post grad had me even more muddled.One look at this article on
the morning of the test was enough to make me take my test confidently and do it
well! The way you simplified it while highlighting important points is crazy. I was
trying to remember all the values given from the typical IR frequency table which
wasn’t working at all and was leaving me anxious. Tongues and Swords made it so
simple and memorable. Thanks for all that you do and more! This is Monica Rao all
the way from India!
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James Ashenhurst
June 21, 2023 at 10:30 am
Glad to hear you found it useful! I had a similar experience in undergraduate
and glad that this simplified things for you!
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Grateful student
June 2, 2023 at 1:18 am
i love you, you just saved my life
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AF
January 20, 2023 at 2:23 am
explanation is very easy to understand. thank you
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Bethy Jay
November 18, 2022 at 5:44 pm
Best Explanation so far. Really helpful
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SWAPNIL BIRADAR
August 22, 2022 at 6:39 am
VERY GOOD
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M
December 29, 2021 at 11:20 am
This is so helpful thank you
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Sagar Gyawali
October 16, 2021 at 8:30 pm
Best Review on IR
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James Ashenhurst
October 19, 2021 at 11:08 am
Thank you Sagar.
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Linda
September
Quizzes, 23, 2021 atMechanisms
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Hi James,
Thank you for your very clear tutorials on LOGIN
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Organic interpreting IR spectra. They have been
really helpful to me.
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Roxanne versi
January 30, 2021 at 6:04 am
Thanks I am newbie and this finally made a pathway in my grey cells :)
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Mira Tracy
January 26, 2021 at 1:08 pm
Thanks a lot. This has really helped me I understood everything in it
Reply
Belén
January 26, 2021 at 2:25 am
Thank you so much for this great work. I have one problem: I used to work with
polymers (in my particular case I am working with PVC films). Firstly, I do an FTIR
spectrum of the “as received” PVC film. Next, I carry out a thermal treatment of
the PVC film (below its Tg) and repeat the FTIR. The peaks have not change,
however the intensity of them is different. I have tried to figure out an explanation
for this phenomenon (searching in bibliography), but I didn´t found an answer. Do
you have any idea of why this happen?
thank you very much.
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Sanjay Ghimire Mechanisms and Summary Sheets (Org 1 + Org 2)
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You are absolutely amazing. I feel so happy and satisfied reading this. Your style of
presenting the context is so good. Thank You
Master
Organic for your hard work for us.
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Shae
December 10, 2020 at 9:51 am
Thank you so much. Two month i have struggled about this topic. Full of detail in
simple words with various example. Thank you again
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Spencer
October 16, 2020 at 11:01 am
I am really grateful this lesson is really awesome.
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MJ
August 25, 2020 at 8:04 pm
Thank you so much!! Your post really helped understangding IR :)
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SANA SIDDIQUE
June 30, 2020 at 3:37 am
Thank you so much for this great information sir
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Miranda
June 17, 2020 at 4:26 pm
Thank you!! This is so easy explained and helpful. I have one question: How much
can I trust in my software suggestions? the software of my FTIR instrumen has
some libraries included.
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James Ashenhurst
Master
Organic June 18, 2020 at 10:35 am LOGIN
Chemistry I’m not sure. There can be considerable variability between samples of the
same molecule, depending on how the sample is prepared (thickness of film)
and the amount of water present (which affects hydrogen bonding). The
libraries are a good starting point but not a magic bullet, good when part of
a more holistic approach to combine with other information (e.g. HRMS
data)
Reply
James Ashenhurst
January 16, 2020 at 12:03 pm
Thanks Paul – I was unaware of the overtones in that region. Very helpful, thank
you!
Reply
Paul Wenthold
January 8, 2020 at 11:56 am
One thing you didn’t mention is the carbonyl overtone peaks, which result when
the molecule absorbs two photons of IR light. These show up as weak peaks at 2 x
the carbonyl frequency, so are in that 3300 – 3500 range.
It’s important know about this because beginning students very often assign those
peaks to NH stretches. And it’s not crazy, because NH stretches in monosubstituted
amides can be relatively weak, so it can be difficult to distinguish them.
This isn’t perfect, but, from an instructor perspective, my advice is to avoid the
urge to assign them to amine or amide. If you see a carbonyl, expect to see that
overtone and don’t call it an NH stretch. Now, this means you might miss an amide,
but that alone is not sufficient to conclude it is amide. You would need to verify it
by other means. As noted, amide C=O stretches tend to be lower energy than
other functional groups, but even then I’d be careful about putting too fine a point
on it (absorptions usually come in ranges, not in specific spots – the C=O is 1680:
does that mean it’s amide? Could be, but it could also be a ketone at the edge of
its range; it’s consistent with both). Now, if you have a mass spectrum that
indicates the presence of a N (by having an odd molecular mass), so you know N is
present, then sure, it could be NH stretching. But absent other information that
indicates an amide, my advice is don’t go that direction.
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Istifanus Chindo
November 29, 2019 at 3:44 am
This is the best review I have ever seen-splendid!
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ANJU SHAJAN
November 8, 2019 at 3:44 am
This is an excellent resource on IR for a newbie…love to give this to my students for
reading. Looking for posts on mass spectrometry..
Reply
James Ashenhurst
November 8, 2019 at 12:39 pm
Thanks Anju – appreciate it. This is what I wish someone told me when I was
learning how to interpret IR spectra.
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Christina
October 27, 2019 at 11:34 am
Very clear, lots of examples and well thought out instructions. I feel so much more
confident! Thank you soo much!!!
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James Ashenhurst
October 28, 2019 at 1:14 pm
Great! So glad you feel more confident!
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Pablo
September 26, 2019 at 8:27 pm
Symply
Quizzes, excellent. Please,
Reactions, we needand
Mechanisms MOCSummary
Text book. Sheets (Org 1 + Org 2)
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September 26, 2019 at 8:50 pm
Not happening! But thank you
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Sophia
September 23, 2019 at 1:13 pm
Seriously it is the best of all explanation I have seen ,it really helpful 💖
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Jasmine
August 5, 2019 at 12:39 am
Very helpful. I can understand the materials much better
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Ikeh Victor
March 22, 2019 at 7:16 am
Thanks for the wonderful lecture, my question is how can one identify aromatic or
the benzene ring absorption. Please I also need your email address
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James Ashenhurst
March 29, 2019 at 12:35 pm
Look for the C-H bond stretch below 3000 cm-1. It is not specific for the
aromatic ring but at least points to an sp2 hybridized carbon bonded to H.
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jenny
January 21, 2019 at 9:26 pm
saved my life honestly.
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Chemistry Honestly? Awesome!
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Olivia
December 18, 2018 at 7:26 pm
Best explanation ever ! The only one I understood .. Thank you a lot!
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James Ashenhurst
February 13, 2019 at 7:57 pm
Thanks Olivia! Glad you found it helpful!
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JOSAN
November 16, 2018 at 6:14 am
I was completely lost at lecture on IR but after reading this, i realized its simple
things made difficult. You saved me a failure.
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James Ashenhurst
February 13, 2019 at 7:58 pm
So glad to hear it Josan.
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Harshit Dubey
October 11, 2018 at 4:04 pm
Thanks! This article saved me. Recommended this to all my friends.
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James Ashenhurst
February 13, 2019 at 7:58 pm
Thanks for letting
Quizzes, Reactions, me know Harshit!
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Freeman
July 5, 2018 at 6:28 am
Wow! Thanks – you will never know how much time this saved me.
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James Ashenhurst
February 13, 2019 at 7:58 pm
So glad to hear it Freeman.
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Zeke
March 26, 2018 at 1:23 pm
Excellent explanation! Thank you for all the hard work.
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James Ashenhurst
February 13, 2019 at 7:59 pm
Thanks Zeke!
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Alejandra
March 19, 2018 at 7:49 pm
Thank you! you just saved my life
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James Ashenhurst
February 13, 2019 at 7:59 pm
If it made IR less painful, that’s awesome Alejandra!
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fujr
February 10, 2018 at 8:05 pm
Loved this!!!!!
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James Ashenhurst
February 13, 2019 at 8:00 pm
Great!
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jei
February 4, 2018 at 10:59 am
THANK YOU!!!! THIS SAVED MY LIFE!!!!!!
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James Ashenhurst
February 13, 2019 at 8:00 pm
Hooray!
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Hello
January 13, 2018 at 4:21 am
I knowReactions,
Quizzes, your facultyMechanisms
plans did not work
andout, but you are
Summary so better
Sheets (Org than1 +many
Org 2)
professors! Thank you!Become
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Dr. Priti
January 11, 2018 at 3:52 am
Beautifully explained Sir !!
Best explanation of IR spectra I’ve came across.
Waiting for your next post :)
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James Ashenhurst
February 13, 2019 at 8:01 pm
Thanks!
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Jacob
January 5, 2018 at 12:43 pm
I completely agree with the above posts.
You should Youtube as well my friend. Great job!
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James Ashenhurst
February 13, 2019 at 8:01 pm
I do have a Youtube channel but it has been quite neglected!
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Maribel
December 18, 2017 at 9:01 pm
I COMPLETELY AGREE 100% with the previous praises and comments – you have
been a SAVING grace in my organic chemistry understanding and I appreciate
your approach in simplifying the most complex things. I have honestly spent 4+hrs
in attempting 2 problems in figuring out the structures and feel so much better
moving forward. THANK YOU! Keep up the phenomenal job!
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James Ashenhurst
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Marko
December 18, 2017 at 5:01 am
Thanks for such a great focused article. It’s really very helpful.
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James Ashenhurst
February 13, 2019 at 8:02 pm
Tried to make it useful. If it succeeded, great!
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UCHE
November 15, 2017 at 5:04 am
This is very clear and understandable even to a layman. Thanks a lot
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James Ashenhurst
February 13, 2019 at 8:02 pm
You’re welcome!
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Nitin
May 9, 2019 at 5:41 am
why alkenes group (3000 -3100) & alkyl halides (500 -539) are
added to NORYL (PPE + PS) plastic?
which properties are affected?
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James Ashenhurst
May 13, 2019 at 11:03 am
How do you know the peak in the 3000-3100 isn’t from the
styrene?
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Meg
October 9, 2017 at 5:23 pm
Thank you so much for this guide! Very thorough approach and great explanation.
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James Ashenhurst
May 13, 2019 at 11:26 am
Meg – so glad you’ve found it helpful. Put a lot of work into it!
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HD
October 1, 2017 at 7:10 am
Great work! best I could find in all these years in fact.
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will
September 10, 2017 at 3:13 pm
Never using another website or youtube vid (unless its yours) for help again. You’re
amazing
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madhavi
September 3, 2017 at 3:39 pm
Beautifully explained!
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jessika
February 15, 2017 at 12:51 pm
This isReactions,
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Mechanisms out there! Sheets (Org 1 + Org 2)
and Summary
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Justin kwon
November 25, 2016 at 9:45 am
THIS IS SO HELPFUL!! so many different examples were used and I understand
everything now! Will there be a quick tutorial for carbon and proton NMR as well?
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