BACKGROUND:
Halogenation of the secondary carbon is the main path in both reactions. This preference for halogenation of the secondary carbon is explained by the higher stability of more substituted radicals. They follow the same pattern as carbocations since in both cases we have an sp 2-hybridized carbon lacking an octet. A secondary carbon is a carbon directly bonded to two carbon atoms C-C-C. A tertiary carbon is one that is directly bonded to 3 other carbon atoms C(CH3)3 for example. Now, this will be very important in the generation of carbocations, carbanions, and radicals. A secondary carbon is a carbon atom bound to two other carbon atoms. Ex of primary and secondary carbons in propane: H3C-CH2-CH3 Both the 1st and 3rd carbons would be primary since they are bound to only one other carbon molecule. The middle carbon would be secondary since it is bound to two different carbon atoms (the 1st and the 3rd). The carbon atom which is attached to only one hydrogen atom. If any functional group links to secondary carbon than such compounds are known as secondary compounds. For example: Propan-2-ol, CH 3 CH (OH)CH 3, is a secondary alcohol. Secondary (2°) carbon atom – bonded to two other carbon atoms, Tertiary (3°) carbon atom – bonded to three other carbon atoms, Quaternary (4°) carbon atom – bonded to four other carbon atoms. This can be explained by one of the important properties of carbon and is its tetravalency.
One of the important properties of carbon is its tetravalency. Carbon is a strict octet follower, which means it needs a maximum of 8 electrons to form stable compounds. Since a carbon atom has 4 valence electrons, it can form up to 4 bonds with different elements. Part of the reason why there are millions of compounds of carbon is its possibility of forming very stable bonds with another carbon atom.
A carbon atom in an organic compound is labeled or classified based on the number of bonds and type of atoms attached to it. In this post, we will specifically focus on the classification of carbon based on the number of other carbon atoms attached to it.
Carbon can be classified as primary, secondary, tertiary or quaternary depending on the number of carbon atoms it is bonded to. This classification only applies to saturated carbons. The classifications are as follow:
- Primary Carbon (1°) – Carbon attached to one other carbon
- Secondary Carbon (2°) – Carbon attached to two other carbons
- Tertiary Carbon (3°) – Carbon attached to three other carbons
3-methylpentane
If we look at the example above of 3-methylpentane, C 1 is attached to three hydrogen atoms and only one carbon atom. This means based on the classification described above, C1 is a primary carbon. On the other hand, C2 is connected to only 2 hydrogen atoms and 2 other carbon atoms. In this case, C2 is considered a secondary carbon. Lastly, C3 is connected to only one hydrogen atom and three other carbon atoms. In this case, C3 is an example of a tertiary carbon. Using the classification above, we will know that C5 and C6 are primary carbons while C4 is a secondary carbon.
This classification scheme is important as it also applies in classifying organic compounds with different functional groups. This specifically applies for alcohols, amines, and alkyl halides. It also applies in classifying carbocations and carbanions.
Note: Each vertex in the condensed formula above is a carbon atom. Since the compound does not have multiple bonds, each carbon atom will have the maximum number it can have less the number of other carbon atoms directly attached to them.
MODELLING:
To demonstrate this topic, we’ll model 2-methylbutane using our Duluth Labs Molecular Sets which has the structure shown below:
2-methylbutane, also called isopentane, is a branched-chain alkane containing 5 carbon atoms. This compound is volatile and flammable and is commonly used in the close loops of geothermal powerplants to drive turbines.
Secondary Carbon Atom
Part I -Primary Carbon
Secondary Carbon Atoms
1
1. Get a carbon atom (black) and connect three Hydrogen atoms (white) using shortmedium connectors
2
2. Attach another carbon atom using a medium
Note: Since the 1st Carbon only has one other carbon atom attached to it, then the 1st Carbon is considered a Primary carbon.
Part II - Secondary Carbon
1. To the structure you prepared in Part I, attach two hydrogen atoms to Carbon 2 using short medium connectors. Then, Attach another carbon atom to Carbon 2 using a medium connector and also attach a hydrogen..
Note: Since the 1nd Carbon has two other carbon atoms attached to it, then the 2nd Carbon is considered a Secondary carbon.
Part III - Tertiary Carbon
1. Attach two more carbon atoms to Carbon 3 using medium connectors
Note: Since the 3rd Carbon has three other carbon atoms attached to it, then the 3rd Carbon is considered a Tertiary carbon.
Complete the structure by connecting two hydrogen atoms each to the added carbon atoms using smallmedium connectors.
PRACTICE EXERCISE
How many primary, secondary, and tertiary carbons are present in the 1-sec-butyl-2-methylcyclopentane?
ANSWERS TO EXERCISES
There are four secondary carbon atoms, 3 primary carbon atoms, and 3 tertiary carbon atoms.
secondary Carbon |
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Structural formula of propane (secondary carbon is highlighted red) |
Secondary Carbons In Isohexane
A secondary carbon is a carbon atombound to two other carbon atoms.[1] For this reason, secondary carbon atoms are found in all hydrocarbons having at least three carbon atoms. In unbranched alkanes, the inner carbon atoms are always secondary carbon atoms (see figure).[2]
primary carbon | secondary carbon | tertiary carbon | quaternary carbon |
General structure (R = Organyl group) | |||
Partial Structural formula |
References[edit]
- ^Smith, Janice Gorzynski (2011). 'Chapter 4 Alkanes'. Organic chemistry(Book) (3rd ed.). New York, NY: McGraw-Hill. p. 116. ISBN978-0-07-337562-5.
- ^Hans Peter Latscha, Uli Kazmaier, Helmut Alfons Klein (2016), Organische Chemie: Chemie-Basiswissen II (in German) (7. Auflage ed.), Berlin: Springer Spektrum, p. 40, ISBN978-3-662-46180-8CS1 maint: multiple names: authors list (link)