Unit 2: Organic Chemistry Flashcards
What is organic chemistry?
The study of molecular carbon compounds. Does not include carbonates, cyanides, and oxides.
What is special about carbon?
Carbon has 4 bonding electrons allowing it to create numerous and varied compounds.
What shapes can carbon compounds make?
Chains, rings, spheres, and tubes.
IUPAC organic naming prefixes.In order from least to greatest.
Meth, eth, prop, but, penta, hexa, hepta, octa, nona, deca.
What is the structure of a IUPAC name?
Prefix-parent-infix-suffix.
The prefix is the substituents of the compound.
The parent is how many carbon atoms are in the main backbone.
The infix refers to the number of multiple bonds in the main backbone.
The suffix refers to the family that it belongs to. (Alkanes, alkenes, alkynes)
There are additional parts. Cyclo refers to a ring.
Substituents are preceded by their location, and sorted alphabetically (including their prefix).
If halogens are included, they have their ending replaced with o. (Bromine to bromo) and have numerical prefixes stating their location.
Trans and cis refer to whether the groups of interest are on the opposite side of the double bond, or the same side.
What are hydrocarbons made of?
Carbon and hydrogen. If some of the hydrogen is replaced by other atoms, it is a derivative or hydrocarbons.
What is the carbon backbone?
The longest chain in a hydrocarbon molecule.
What is an alkane?
The simplest of organic compound families.
Chains of carbon atoms connected by single bonds.
Formula is Cn H(2n+2)
What is a saturated organic compound?
Alkanes. The bonding electrons are minimally used for carbon bonds. Remaining electrons are bonded to hydrogen atoms.
What is a line diagram?
Each point of the zigzag is a carbon atom. Hydrogen atoms are not drawn. It is a zigzag. Parts of the line may be a double or triple line depending on the bonds between carbon atoms.
What is a condensed formula?
Ex. Hexane. CH3CH2CH2CH2CH2CH3.
Butene. CH2CH1CH2CH3
Propyne. CHCCH3
How do you determine the numbers used for naming organic compounds?
Find the longest carbon chain (the backbone) and determine the side which results in the lowest numbers. Remember that double or triple bonds take precedence over substituents when numbering.
What is a structural formula?
Shows atomic symbols and the bonds between them (aside from Hydrogen). For example, Butene is C=C-C-C
1-Bromo ethane is Br-C-C
Alkenes are what?
Hydrocarbons that have carbon-carbon double bond(s). Formula is C(n) H(2n).
Alkene naming?
Prefix for number of carbon atoms, followed by 1 number for where the double bond(s) exist. If more than one bond exists, the family name needs a prefix as well.
Example. C=C=C-C is but-1,2-biene
C-C-C-C-C=C-C-C is oct-3-ene
Alkyne naming?
Same as alkenes but family part of names uses yne instead of ene.
What are alkynes?
Same as alkanes and alkenes but with a triple carbon bond. Formula is C(n)H(2n-2)
What do you need to remember about alkyne line diagrams?
Bonds on either side of the triple bond are straight (no rotation)
What is a cycloaliphatic?
Alkanes, alkenes, and alkynes, are all aliphatics and can exist in rings.
Cycloaliphatics naming?
Cyclo prefix is used before the carbon backbone name.
Ex. 1,2,4 trimethyl CYCLOhexane (do not actually capitalize like this)
What is an isomer?
When two or more compounds have the SAME CHEMICAL FORMULA but DIFFERENT ARRANGEMENT OF ATOMS and different physical properties, they are called isomers. There are two types, stereoisomers and structural isomers.
What is a structuralisomer?
Molecules with the same formula are bonded together in different orders and have different names. For example, Pent-1-ene and pent-2-ene are structuralisomers. (Remember that there is no Pent-3-ene because it is the same as pent-2-ene).
What is a stereoisomer?
Same molecular formula (and sort of the same names). They only occur in organic compounds with double bonds.
Naming: When groups of interest (any atoms that are not hydrogen) are on the same side, prefix with cis (cis = same). When they are on the opposite side, use trans (trans=opposite).
For example, but-2-ene can have the CH3s on the end on the same side of the double bond, or the opposite side. Cis-but-2-ene compared to trans-but-2-ene.
Why did the food industry like to use transfats?
Transfats have trans orientations, giving them lower melting points and extending their shelf-life. This was ideal for things such as margarine (which would use transfats) compared to butter.
What is a functional group?
A specific group of atoms within a molecule that affects the properties of the compound. Multiple bonds are considered a functional group and alter the compounds properties.
What type of bond is stronger/weaker? Between single and double or triple bonds.
Double and triple bonds are weaker than single bonds and can break to create free bonding electrons to bond with other elements or functional groups.
What is hydrogenation?
When an alkene or alkyne combines with hydrogen to form an alkane. (To saturate a compound)
What is halogenation?
When an alkene or alkyne combines with an element from the halogen family (group 7A)
When a hydrohalide combines with a hydrocarbon, what rule does it follow?
Markovnikov’s rule which states: the hydrogen will bond to the carbon atom in the double bond that has the most hydrogen already bonded to it. The halogen bonds to the other carbon.
What is hydration?
When an alkene or alkyne combines with water. The water molecule breaks into a single hydrogen and hydroxyl group (OH). Follow Markovnikov’s rule if applicable.
What are hydrocarbons with a hydroxyl group known as?
Alcohols
How do additional double bonds affect naming
You add a prefix to the suffix
Ex. Pent-1,2-diene
How does an aliphatic forming a ring affect naming
Cyclo goes before the parent
Ex. Cyclopentene
Naming alcohols
ol is suffix
Example, OH-C-C is ethanol
C-C-C with OH attached to second carbon is propan-2-ol
If more than one OH present, prefix the family name and add ol
Ex. 2 OH; diol
Use numbers between suffix and family name
Ex C-C-C with OH one first and second, is propan1,2diol
What does IUPAC stand for?
International Union of Practical Applied Chemists
How do you name the substituents of an organic compound?
find how many of each compound exist (to find their prefix) then sort alphabetically (including prefix). Find the side from which to start iterating through the carbon chain by determining which side will result in the lowest numbers (prioritising lower numbers for double or triple bonds in alkanes or alkynes respectively). They follow the structure of #, #… - {number of same substituents prefix}{type of substituent ending in yl}
For example, if CH3 is attatched twice on the first atom and once on the third of a carbon backbone, 1,1,3-trimethyl
Example 2. CH2=CH-CH-CH3 with ethyl attatched to the CH connected to CH3… 3-ethyl but-1-ene (1 in butene is optional)
Can organic compounds be molecular or ionic?
Organic chemistry is the study of molecular carbon compounds. Electrons are shared
What is a derivative of hydrocarbons?
A hydrocarbon in which some or all of the hydrogen atoms have been replaced by other atoms
What is a substituent group?
Groups of atoms off the main chain
2 compounds with the same chemical formula but different order of atoms and different physical properties are what
Structural isomers
2 compounds with the same formula and order but differ in 3d-orientation of atoms in space are what
Stereoisomers
What is trans fat?
Fats are just long hydrocarbon chains that can be saturated. Trans fats are fats that are in a trans orientation. Fat can also be saturated to achieve the same effects.