Nomenclature 455v68

IUPAC Nomenclature Naming Molecules by Following the Rules

Getting Started… • You first have to identify the “family” that your molecule belongs to… • So, check for functional groups… • If there are none, then your molecule is simply an alkane…

The Three Basic Parts • The name for any organic molecule consists of three basic parts: Prefixes-Parent-Suffix • Each part of the name has a purpose.

Basic Part - Suffixes • Suffixes on the end of the name of an organic molecule tell you what major family the molecule belongs to • The suffix for an alkane is “-ane”

Basic Part – the Parent • The “parent” part of the name tells you how many carbons are in the main chain of the molecule • The main chain of the molecule is defined for alkanes as being the longest chain in the molecule

Parent and suffix… • The parent is named based on the number of carbons • 1 carbon = “meth” • So a one-carbon alkane is called methane

CH4

Parent and suffix… • 2 carbons = “eth” • So a two carbon alkane is called ethane.

CH3CH3

Parent and suffix… • 3 carbons = “prop” • So a three carbon alkane is called propane.

CH3CH2CH3

Parent and suffix… • 4 carbons = “but” • So a four carbon alkane is called butane.

CH3CH2CH2CH3

And now the rest… • • • • • •

5 carbons = “pent” 6 carbons = “hex” 7 carbons = “hept” 8 carbons = “oct” 9 carbons = “non” 10 carbons = “dec”

• So be brilliant and name the following alkane (shown as both condensed formula and a skeletal structure) CH3CH2CH2CH2CH2CH2CH2CH2CH3 or

Answer? • That’s right! • nine carbons + alkane family = NONANE • One more thing - Should you have two or more chains that are the same length, the parent is the one with the most prefixes… • But - We need to talk Prefixes first… we’ll come back to this…

Here we go – the Prefixes • Prefixes are the bits and pieces that are attached to the main chain (parent) of the molecule. • An example of a prefix might be a halide attached to the main chain as in: Br

Prefixes – the Halides • The family called alkyl halides does not have a suffix. • Halides are always named as prefixes. • Fluorine is called “fluoro” • Chlorine is called “chloro” • Bromine is called “bromo” • Iodine is called “iodo”

Putting together a name… • The rules for IUPAC nomenclature include: • Step 1: Find the main chain • Step 2: Number the main chain • Step 3: Identify all prefixes and their position numbers • Step 4: Write the full name: PrefixesParent-Suffix

Now let’s take a look: • Follow the rules… Name this molecule… Br

Find the main chain… • The longest chain in this molecule has seven carbons… and only a halide (which is always named as a prefix). Br

• This will be a heptane.

Number the chain… • This molecule is symmetrical. It doesn’t matter if we go left to right or right to left… that bromine is attached to carbon #4 Br 4

Final Answer? • If you put the prefix first, then parent and suffix, what do you get? Br 4

• “Bromo hept ane” includes all of the pieces, except for indicating where the bromine is attached... • 4-bromoheptane is the complete name.

What would you do different..? • How would you name this one? Br

• Number this asymmetric molecule by beginning your numbering from whichever end is closest to the first substituent (aka: branch, prefix).

So in this case… • You would number from left to right, so the bromine winds up on position #3. Br

• If you numbered from the other end, the bromine would be on #5. • Always aim for the lowest possible number on the first substituent!

Final Answer (again)? • 3-bromoheptane Br

More Prefixes • The most common prefixes we have in organic molecules are those little fragments of carbon pieces attached to the main chains. • The carbon fragments are called “alkyl groups”. They all end in “-yl” to indicate they are fragments of a bigger molecule.

Alkyl Groups • Alkyl groups are named similarly to alkanes, based on the number of carbons in the fragment. • A fragment of methane, CH4, would be CH3• This fragment is called “methyl” where “meth” stands for one carbon and “yl” stands for fragment (alkyl group).

Methyl Group • The molecule shown here has a 7-carbon main chain.

• Notice that it has a branch attached to carbon #4. This branch has a single carbon – a methyl group. • 4-methylheptane is the name of this compound.

Ethyl Groups • A two-carbon alkane is called ethane, CH3CH3. The corresponding two-carbon fragment is always CH3CH2-, which is called “ethyl”.

• 4-ethylheptane is the name for this one.

Propyl Groups • There are two possible three-carbon alkyl groups to form from propane, CH3CH2CH3. • The straight chain version: CH3CH2CH2which is called “propyl” or “n-propyl” (where n stands for “normal” or straight-chained)

Isopropyl Groups • There are two possible three-carbon alkyl groups to form from propane, CH3CH2CH3. • The other possibility is to form the fragment on the central carbon: CH3CHCH3, which is called “isopropyl”

Butyl Groups • There are two possible four-carbon alkyl groups to form from butane, CH3CH2CH2CH3. • One possibility is to form the fragment on one of the end carbons: CH3CH2CH2CH2-, which is called “butyl” or “n-butyl”

Sec-Butyl Groups • The other possibility is to form the fragment one of the central carbons: CH3CHCH2CH3, which is called “secbutyl”. [Note that the carbon second from the left only has three bonds – so that’s where its bonding to the main chain]

Isobutyl Groups • There are two other possible fourcarbon alkyl groups to form from isobutane, (CH3)3CH. • One is formed as a fragment on one of the three symmetrical end carbons: (CH3)2CH(CH2)-, which is called “isobutyl”

Tert-butyl Groups • The other is formed as a fragment on the one central carbon, (CH3)3C-, which is called “tert-butyl”

What alkyl groups do you see? • There’s two groups attached to the ring below. What are they?

What alkyl groups do you see? • The group in red has two carbons and is an ethyl group. • The group in blue has four carbons. Three in a row and the extra attached at the middle carbon. Its an isobutyl group.

What alkyl groups do you see? • There’s two groups attached to the ring below. What are they?

What alkyl groups do you see? • The group in red has three carbons attached at the middle carbon and is an isopropyl group. • The group in blue has four carbons, in a row, attached at one of the middle carbons. It’s a sec-butyl group.

More about Prefixes… • Every prefix needs a position number… • And prefixes are always alphabetized by their first letter: – Methyl is an “m” – Ethyl is an “e” – Propyl is a “p” – Isopropyl is an “i” – Sec-butyl is a “b”… (Say what??)

Alphabetizing Prefixes… • Sec-butyl and tert-butyl both have a descriptive prefix that tells you the structure of those alkyl groups... (the prefix has a prefix!) • When alphabetizing, we do NOT use these descriptive prefixes (like sec- or tert-) to alphabetize…

Continuing with Prefixes… • If you have multiples of the same prefixes, like two bromines in the same molecule, you COULD name them separately or you could combine them into a single prefix name and include “di” in front to indicate TWO of them. Br • 3,4-dibromohexane! Br

Continuing with Prefixes… • Di-, tri- and tetra- are more prefixes for the prefixes. • - when alphabetizing for names, prefixes are never alphabetized using a “prefix” like di- or sec-. – Sec-butyl is a “b” – Dimethyl is a “m”

Name the following molecule: • Keeping all of the rules in mind, what would you name this molecule:

And the answer is…? • Longest chain: nine carbons • Number: left to right (hit that first branch on #4) • Group on #4 is methyl. 4 5 • Group on #5 is isopropyl. • Alphabetize! • 5-isopropyl-4-methylnonane.

About that main chain again… • Recall that we said if you had two chains the same length, the parent is the one with the most branches. Which is the parent in this example?

Where’s the Parent? • There are two options: Option 1 is highlighted in red:

• Option 2 is highlighted in blue:

And the winner is… • The red one has two branches:

• The blue one has three branches:

• The blue one is the parent. • Write that name…

Finally… the name… • • • • • • • •

Eight carbons in main chain. Octane. Number left to right (first branch on #2!) Three alkyl groups attached: 6 2-methyl 2 5 5-propyl 6-methyl Simplify prefixes by using 2,6-dimethyl Full name: 2,6-dimethyl-5-propyloctane.

The last kind of alkyl groups – Complex Branches • Complex branches are those that have no simple name, yet they still need to be named.

• Identify the complex branch and its point of attachment.

Naming Complex Branches • Find the point of attachment inside the complex branch itself, first.

Naming Complex Branches • Number the longest branch of that complex branch, starting from the point of attachment, #1. In this case, propyl is the miniature parent. 3

2 1

Naming Complex Branches • Identify the prefixes on that little miniature parent (in this case, the propyl chain) of the complex branch, and their position numbers. • In this example, there are two methyls attached to #1. 3

2

1

Naming Complex Branches • Write the full name, placing the complex branch inside brackets. This complex branch is attached to #5 of the original main chain so: • 5-[1,1-dimethylpropyl]nonane is the 2 name. 3

1

Now: Cyclic Compounds • When naming cyclic compounds, first determine if the ring is the parent, or not. • If the ring has more carbons than any of the alkyl groups attached, the ring is the parent. • If not, the ring becomes a cycloalkyl group and is a prefix for the main chain.

Cyclic Compounds – Parent? • In this example, the ring has four carbons and the chain has eight.

• The chain is the parent and the ring is a prefix. • The ring is a cyclobutyl group on #1. • 1-cyclobutyloctane.

Cyclic Compounds • In this example, the ring has five carbons and the alkyl group has three.

• The five-carbon ring is the parent and is called cyclopentane. • The one alkyl group will be on #1 (of course – that #1 isn’t even needed!) • Propylcyclopentane is the name.

Cyclic Compounds • Word of caution: don’t double dip… its really easy to double count the carbon (*) that the alkyl group is attached to. • Alkyl groups are only those BEYOND the ring carbons. Thus, this is a propyl group not a butyl group. *

1

3 2

Cyclic Compounds – Multiple Groups • When a ring has multiple groups, the rule for numbering is: “Number around the ring so as to arrive at the lowest possible sum of the position numbers”. • The sum in this molecule is 1 + 3 = 4. 1 3

Cyclic Compounds – Multiple Groups • How about this one?

Cyclic Compounds – Multiple Groups • Lowest possible sum? 4 1

• 1+2+4=7

2

Cyclic Compounds – Multiple Groups • If you have two possibilities for lowest possible sum, THEN (and only then) you should alphabetize to prioritize your groups. • What about this one?

Cyclic Compounds – Multiple Groups • Two possible “lowest sums” of 4, where the groups must be on carbons #1 and #3. • Prioritize by alphabetizing – the ethyl will be #1 and the isopropyl will be #3.

• Name? 1-ethyl-3-isopropylcyclopentane

Cyclic Compounds – Two groups • Last comment – when you have two groups attached to a molecule, they can potentially either both face up (or down) in the same direction (CIS) or one faces up and the other faces down (TRANS) • We use wedges to indicate “up” or towards you and dashes for “down” or away.

Cyclic Compounds – Two groups

CIS

TRANS

• The molecule on the left has two methyl groups facing down (CIS) and the one on the right has one down and one up (TRANS).

Cyclic Compounds – Two groups • Incorporating that into the name: Place the term “cis” or “trans” in the beginning of the name, before the first prefix

• Name? CIS-1,2-dimethylcyclohexane

Finale • I think this covers everything that you should know and be able to do for naming basic alkanes and cycloalkanes. • As we add more families (alkenes, alkynes, etc) we will build on this “foundation” of nomenclature rules… • Good luck…