Naming Carboxylic Acids - Organic Chemistry IUPAC Naming by Leah4sci

Summary

This 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

00:00

🧪 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.

05:03

🔍 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.

10:03

📢 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.

Keywords

💡Carboxylic Acid

A carboxylic acid is an organic compound that contains a carboxyl functional group, which consists of a carbonyl (C=O) and a hydroxyl (OH) group attached to the same carbon. In the context of the video, carboxylic acids are the main focus, and the script explains how to name them according to IUPAC rules. The video emphasizes that the carboxyl group is always considered as the terminal and highest priority functional group in the naming process.

💡IUPAC Naming

IUPAC (International Union of Pure and Applied Chemistry) naming is a systematic method of naming chemical compounds to ensure that each compound has a unique and clear name. The video script discusses how to apply IUPAC rules to name carboxylic acids, highlighting the importance of the carboxyl group's position and the separation of words in the compound's name.

💡Carboxyl Group

The carboxyl group is a functional group in chemistry composed of a carbon atom double-bonded to an oxygen atom and single-bonded to a hydroxyl group. The script explains that this group is represented as -COOH and is central to the naming of carboxylic acids, always being assigned the number 1 in the naming sequence.

💡Functional Group

A functional group is a specific group of atoms within a molecule that is responsible for the characteristic chemical reactions of that molecule. In the video, the carboxyl group is the key functional group of carboxylic acids, and its position and priority dictate the naming of the compound.

💡Parent Chain

The parent chain is the longest continuous carbon chain in a molecule that serves as the base for naming. The script clarifies that when naming carboxylic acids, the parent chain is chosen such that the carboxyl group is at the end of the chain, which is a departure from the usual rule of choosing the longest chain.

💡Substituents

Substituents are the atoms or groups of atoms that are attached to the parent chain in a molecule. The video script provides examples of how to name molecules with substituents like methyl and chloro groups, explaining how they are incorporated into the final name of the carboxylic acid.

💡Numbering

Numbering in IUPAC naming refers to the systematic assignment of numbers to carbon atoms in a molecule to indicate the position of functional groups and substituents. The video emphasizes that for carboxylic acids, the carboxyl group is always assigned the number 1, and other groups are numbered accordingly.

💡Suffix

A suffix in IUPAC nomenclature is a group of letters added to the end of a name to indicate the type of compound. For carboxylic acids, the suffix '-oic acid' is used, as explained in the script, to denote the presence of the carboxyl group.

💡Prefix

A prefix in IUPAC nomenclature is used to denote the position and type of substituents on the parent chain. The script illustrates how prefixes like '2-methyl' and '5-chloro' are used to indicate the presence and position of substituents on the parent chain of a carboxylic acid.

💡Alcohol

An alcohol is an organic compound with a hydroxyl (OH) group but without a carbonyl group bonded to the same carbon. The script contrasts alcohols with carboxylic acids to clarify that the presence of a carbonyl group is what distinguishes carboxylic acids from other compounds with hydroxyl groups.

💡Aldehyde

An aldehyde is an organic compound containing a carbonyl group with the double bond between carbon and oxygen and a hydrogen atom attached to the carbonyl carbon. The script uses aldehydes as a comparison to carboxylic acids, noting that the position of the carbonyl group determines whether the compound is an aldehyde or a ketone.

💡Ketone

A ketone is an organic compound with a carbonyl group in which the carbonyl carbon is bonded to two other carbon atoms. The video script explains that when a ketone is present alongside a carboxylic acid, it takes a lower priority and is referred to as an 'oxo' group in the naming.

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

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