Naming Carboxylic Acids - Organic Chemistry IUPAC Naming by Leah4sci
Summary
TLDRThis video tutorial explains how to name carboxylic acids using IUPAC rules. It covers the basic structure of a carboxylic acid and how to identify and number the parent chain. The video also discusses naming with multiple substituents, handling multiple carboxyl groups, and differentiating between aldehydes and ketones. Examples are provided to illustrate the process, and tips for organic chemistry success are shared.
Takeaways
- 📘 Carboxylic acids are identified by the carboxyl functional group, consisting of a carbonyl (C=O) and hydroxyl (OH) group.
- 🧪 Carboxylic acids are terminal functional groups and always receive the highest priority in IUPAC naming, with the carboxyl carbon assigned as carbon number 1.
- 🧩 The general formula for a carboxyl group can be written as R-COOH, where 'R' represents the remaining molecule.
- ✏️ To name a carboxylic acid, follow IUPAC naming rules and add the suffix '-oic acid' to the parent chain name, dropping the 'e' when appropriate.
- 🔢 Multiple substituents are named with their positions indicated by numbers, and substituents are listed in alphabetical order in the final name.
- 🔄 When a molecule contains more than one carboxyl group, each is assumed to be terminal, and the name is modified to include 'dioic acid' without needing to number the groups.
- 🔬 For cyclic compounds, the ring is named with the suffix '-carboxylic acid' attached to the parent chain name, indicating the presence of a carboxyl group on the ring.
- ⚖️ If both a carboxyl and a carbonyl (ketone or aldehyde) are present, the carboxyl group takes precedence in numbering, and the carbonyl gets the prefix 'oxo-' in the name.
- 📊 Aldehydes and ketones are distinguished by their position in the chain: aldehydes at the end, ketones in the middle.
- 📚 More advanced naming concepts include recognizing derivatives of carboxylic acids such as esters and amines, which will be discussed in future videos.
Q & A
What is the basic structure of a carboxylic acid?
-A carboxylic acid is characterized by a carbonyl carbon double-bonded to an oxygen and a single bond to a hydroxyl group (OH). It can be represented as RCOOH or RCO2H, where R represents the rest of the molecule or a carbon chain.
How does the carboxyl functional group differ from an alcohol or an aldehyde?
-The carboxyl group is distinguished by the presence of a carbonyl (C=O) bonded to an oxygen which is also bonded to a hydrogen (OH). In contrast, an alcohol has a hydroxyl group (OH) without a carbonyl, and an aldehyde has a carbonyl bonded to a hydrogen instead of an oxygen-hydrogen group.
What is the IUPAC naming rule for carboxylic acids?
-In IUPAC nomenclature, carboxylic acids are named by adding the suffix '-oic acid' to the name of the longest carbon chain that includes the carboxyl group, which is always considered as carbon number 1.
Why is the number 1 often omitted in the naming of carboxylic acids?
-The number 1 is understood to be the position of the carboxyl group in carboxylic acids, so it does not need to be explicitly stated in the name.
How do you name a carboxylic acid with substituents?
-You identify and number the parent chain, assign the carboxyl group the number 1, and then list substituents in alphabetical order as prefixes before the parent chain name and the '-oic acid' suffix.
What happens when there are multiple carboxylic acid groups in a molecule?
-When there is more than one carboxyl group, they are both considered terminal and given the highest priority, resulting in the suffix '-dioic acid'. The numbers do not need to be included in the name.
Can you provide an example of naming a carboxylic acid with a ring?
-A carboxylic acid attached to a ring is named by first identifying the ring as you would normally, then adding the '-oic acid' suffix. For example, a five-membered ring would be named 'cyclopentane-oic acid'.
What is the difference between naming a ketone and an aldehyde in a carboxylic acid derivative?
-In carboxylic acid derivatives, a ketone or aldehyde is demoted to an axial substituent and given the prefix 'oxo'. The difference between the two is determined by their position on the parent chain; an aldehyde is at the end (number 1), and a ketone is in the middle.
How do you interpret a complex name with two 'oxo' prefixes in a carboxylic acid?
-When a name has two 'oxo' prefixes, it indicates the presence of two carbonyl groups. The position of these groups on the parent chain determines whether they are aldehydes or ketones.
What is the significance of the term 'dioic acid' in IUPAC nomenclature?
-The term 'dioic acid' in IUPAC nomenclature signifies that there are two carboxylic acid groups present in the molecule.
How does the presence of a carboxylic acid affect the numbering of the parent chain?
-The presence of a carboxylic acid affects the numbering of the parent chain by making the carbonyl carbon the first carbon, regardless of the total length of the chain.
Outlines
🧪 Understanding Carboxylic Acids
The script introduces carboxylic acids, explaining their chemical structure and how to name them according to IUPAC rules. It emphasizes the carboxylic acid's structure, which includes a carbonyl group (C=O) bonded to a hydroxyl group (OH). The video demonstrates how to identify the parent chain and highlights the carboxylic group's priority in numbering. It provides examples of naming simple and complex carboxylic acids, including those with substituents and multiple carboxylic groups. The script clarifies that the carboxylic group is always considered terminal and is assigned the number 1 in naming, unless there are multiple carboxylic groups, in which case they are both terminal and do not require numbering.
🔍 Advanced Carboxylic Acid Nomenclature
This section delves into more complex scenarios of carboxylic acid naming, such as when the molecule contains a ring or another carbonyl group. It explains how to handle symmetrical molecules and those with substituents like isopropyl groups. The video also addresses the situation where a carboxylic acid is attached to a ring, using 'cyclo' to denote the ring and 'carboxylic acid' as a suffix. It further discusses how to differentiate between ketones and aldehydes when they are present alongside carboxylic acids, assigning them the prefix 'oxo' and demoting their functional group status to an axial substituent. The script provides examples to illustrate these concepts and suggests resources for further learning.
📢 Engaging with Organic Chemistry Resources
The final paragraph shifts from the technical discussion to promoting additional resources for students struggling with organic chemistry. It invites viewers to download an ebook titled '10 Secrets to Acing Organic Chemistry' and to explore options for online tutoring. The script encourages engagement by asking viewers to subscribe, like, share, and comment on the video for further questions or interaction. It also directs viewers to the creator's Facebook page for more personalized support.
Mindmap
Keywords
💡Carboxylic Acid
💡IUPAC Naming
💡Carboxyl Group
💡Functional Group
💡Parent Chain
💡Substituents
💡Numbering
💡Suffix
💡Prefix
💡Alcohol
💡Aldehyde
💡Ketone
Highlights
Carboxylic acids can be simplified as R-COOH, where R represents the rest of the molecule.
The carbonyl carbon is double-bonded to an oxygen and single-bonded to an OH.
The carbonyl and OH together form the carboxyl functional group.
Carboxylic acids are named following IUPAC rules by adding 'acid' to the end.
The carboxyl group is always considered as number 1 in IUPAC naming.
The parent chain is identified and highlighted for naming.
The carboxylic acid's position is always understood to be number 1, so it's often omitted.
The suffix 'oic acid' is used for carboxylic acids.
Substituents are named and placed in alphabetical order before the parent chain and suffix.
When there are multiple carboxylic groups, they are both terminal and do not require numbering.
The suffix 'dioic acid' is used when there are two carboxylic acid groups.
The longest carbon chain is not always the parent chain due to the high priority of the carboxylic acid group.
Carboxylic acids coming off a ring are named by adding 'carboxylic acid' to the ring name.
When another carbonyl group is present with a carboxylic acid, it gets the prefix 'oxo'.
The difference between an aldehyde and a ketone is determined by their position on the parent chain.
The ebook '10 Secrets to Acing Organic Chemistry' is available for download.
Online tutoring services for organic chemistry are offered.
The video encourages viewers to subscribe for more related content.
Transcripts
laya hair from labor sicom and in this
video i will show you how to name
carboxylic acids a carboxylic acid can
be simplified as showing R which means
the rest of your molecule or some carbon
chain bound to a carbonyl carbon which
is a C double bound to an O and then
single down to a no H the carbonyl
together with the o H make up your
carboxyl functional group so don't
confuse this with the molecule that
simply has an O H as this is an alcohol
or similar carbonyl containing
functional groups such as a C double
bond o but an H instead of an O which is
an aldehyde or recei double bound o with
another R group which is a key film
the carboxyl group can also be
represented as RC o o H or RC o 2h where
the two oxygens represent the carbonyl
oxygen and the Oh a Choksey jiin to name
a carboxylic acid you follow the
standard rules for IU pack naming and
simply add a wick acid to the end this
is a rare case in IU pack naming where
you have a separation between two words
as part of the parent name one more
thing to recognize about the carboxylic
acid is that the functional group by
definition is terminal and since the
carboxyl is a high priority functional
group it will always be number 1 let's
start with a simple example by
identifying and highlighting the parent
chain since the carboxylic acid is a
high priority functional group the
carboxyl group always gets number 1 and
i number the rest of the molecule
accordingly having 4 carbons in my
parent chain gives me a first name of
vugt only single bonds gives me a last
name of thing since the carboxyl group
shows off a number one i would include
100 ik acid however the number one is
always understood and does not have to
be included and since the suffix starts
in a vowel i drop the e this gives me a
final name of butanoic acid let's try
this example that has multiple
substituents i first start by
identifying and highlighting my parent
chain and give carboxyl the number 1
since this is a somewhat complex
molecule I want to make sure that I have
all my puzzle pieces in place before
putting the name together a total of 6
carbons gives me a first name of hex the
PI bond at number 3 gives me a last name
of 3e
my carboxyl functional group gives me
the ending oayk acid where the number 1
is understood and therefore emitted a
one-carbon substituent on carbon 2 gives
me the prefix of 2 methyl and a sale
substituent on carbon 5 gives me the
prefix 5 chloro
putting the same together I start with
my prefixes in alphabetical order
followed by my first name last name and
suffix since I have a methyl and a clora
substituent C comes before M putting the
chloro before the methyl and since the
suffix starts in a vowel I drop the e in
E for a final name of five chloro two
methyl three hexanoic acid given that
this name is long I will go back to my
checklist to ensure that I have all the
pieces that's five chloro two methyl
three hex e no ik acid when I have more
than one carboxyl group on the molecule
they both get highest priority and
therefore will assume to be terminal and
the numbers do not have to be included
in this case I start by identifying and
highlighting my parent chain when
numbering this chain I get a number one
on the right for a carboxyl and the
number one on the left for a carboxyl
however if I put a two on the right I
don't have any substituents but a two on
the left
gives me a methyl group and so a number
from the left five carbons gives me a
first name of pent only single bonds in
the chain gives me a last name of a
since the carboxylic acids are assumed
to be first and last I don't have to
include the number I simply put the
suffix dioic acid a one-carbon
substituent on two gives me the prefix
of two methyl for a final name of two
methyl pentane dioic acid notice that i
didn't drop the e inane given that I
starts with a consonant and also
recognize that even though I don't have
numbers for the two carboxylic acids the
fact that I have pent implies that the
first carbon and the last or the fifth
carbon are both my carboxylic acids this
concept becomes even more evident when I
have a tricky example like this one my
longest carbon chain does indeed have
six carbons however this is not my
parent chain because the carboxylic acid
is such a high priority group it doesn't
matter how many carbons are in the chain
as long as you are able to connect
carboxyl number one and carboxyl number
two to make your parent chain this gives
me an unexpected parent chain of only
four instead of six carbons
we're carboxyl number one is first and
carboxyl number two is last the four
carbons give me a first name of Bute
only single bonds of the chain gives me
a last name of pain since this is a
symmetrical molecule it didn't matter if
I started numbering from the top or the
bottom I have two isopropyl substituents
coming off of both carbon 2 and carbon 3
if you're not comfortable identifying
the isopropyl group go back to my video
on naming branch substituents giving me
the prefix to 3 diisopropyl and my two
carboxyl groups give me the ending of
dioic acid putting the same together i
get 2/3 diisopropyl butanediol gas
when you have a carboxylic acid coming
off a ring substituents
you simply name the ring as you would
and then add the prefix carboxylic acid
in this case I have a five membered ring
giving me pent for five and cyclo for
the rink only single bonds gives me a
last name of a m-- and a carboxylic acid
gives me the ending carboxylic acid this
gives me a final name of cyclopentane
carboxylic acid when you have another
carbonyl in your molecule with your
carboxylic acid it automatically gets
the lower priority and regardless of
having a ketone or an aldehyde they both
get the prefix bock so let's take a look
at these two examples for the first one
we have four carbons where I have a
carboxyl on number one and a ketone on
number three for the second example I
have only three carbons with the
carboxyl getting the number one and the
aldehyde getting the number three the
first chain of four carbons gets the
first name of Bute and a last name of
ane for only single bonds the ketone on
carbon three gets demoted from the own
functional group to the axial
substituent for a prefix of three ox o
and the carboxylic acid of course gets
the ending Olek acid for my second
example three carbons gives me a first
name of pro only single bonds gives me a
last name of aim and aldehyde on carbon
three gets demoted from the AL
functional group to the axial
substituents of three EXO and of course
the ending Loic acid and so i get an
interesting phenomenon the first
molecule has a final name of three acts
so butanoic acid and my second molecule
gets a final name of three acts o
propanoic acid what you want to
recognize here is that you're known
carboxyl carbonyl gets the prefix ox o
and the way you identify between a
ketone or an aldehyde is simply by where
it shows up on the parent chain so what
do you do if you're given a name that
has two axes in it but doesn't tell you
if it's an aldehyde or ketone remember
the difference is simply we
shows up in the molecule and so when you
draw it if it happens to come out at the
end it's an aldehyde if it happens to
come out in the middle its a ketone we
identify the first name which tells me I
have a five carbon parent chain and only
single bonds from the last name aim
since my suffix is Olek acid I know that
I have a carboxyl functional group on
carbon number one and I can draw this on
the right or the left once I determine
where the carboxyl group is situated I
numbers starting from that side I have
two acts or substituents located on
carbon three and carbon five so I'll
simply add a double bound
oh and see where that shows up on carbon
three given that it's the middle of the
molecule
I recognize it as a ketone and carbon
five given that it's the end of the
molecule
I recognize that to the in a lot the
apparent complexity of a name Folio
instead simply apply the puzzle piece
concepts backwards by first identifying
your first and last name finding your
functional group and adding your
substituents in future videos we'll look
at how to name derivatives of carboxylic
acids including esters and amines
are you struggling with organic
chemistry are you looking for
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