Orgo Chemistry I: Quiz 2~ IUPAC Naming, Resonance Patterns

Parent name for Alkane with 1 Carbon

methane

Parent name for Alkane with 2 Carbons

ethane

Parent name for Alkane with 3 Carbons

propane

Parent name for Alkane with 4 Carbons

butane

Parent name for Alkane with 5 Carbons

pentane

Parent name for Alkane with 6 Carbons

hexane

Parent name for Alkane with 7 Carbons

heptane

Parent name for Alkane with 8 Carbons

octane

Parent name for Alkane with 9 Carbons

nonane

Parent name for Alkane with 10 Carbons

decane

Prefix of an alkyne in a ring configuration

cyclo-

What is a constitutional isomer?

Molecules with the same molecular formulas but with different arrangements of molecules that are bonded to each other in different ways

What oribital is an atom in if it can display resonance? Why?

sp2 because it must have an available p orbital 

What is it called when there is a lone pair but they cannot exhibit resonance?

The lone pair is localized

Why do molecules exhibit resonance? (not a pattern)

delocalizing the electrons distributes the charge throughout the molecule and lowers the overall energy

Name the 5 patterns that indicate a molecule has resonance

1. having a lone pair 1 sigma bond away from a pi bond

2. having a pi bond 1 sigma bond away from a positively charged molecule

3. having a pi bond 1 sigma bond away from another pi bond

4. having a lone pair 1 sigma bond away from a positively charged molecule

5. having a pi bond between 2 atoms with very different electronegativities

What is the highest priority for determining most significant resonance contributor?

All molecules having a complete octet even if they don’t usually have them.

What is the ranks of most important factors for most significant resonance contributors?

first is having complete octets on all atoms, second is having the least amount of formal charges, making sure that the charges align with the electronegativity (e.g oxygen having a negative charge and carbon having a positive charge), and having charges that are closer together in the overall structure

What is the real molecule called that all resonance structures contribute to?

resonance hybrid

What is the definition of an Alkane?

hydrocarbon with only sigma bonds

What suffix do you put in front of an Alkane/ hydrocarbon that has all the carbons in a straight line?

“n-” which stands for normal

What are the greek prefixes for 1-6 in chemistry

mono, di, tri, tetra, penta, hexa

Can you include the molecules in rings in determining the parent Alkane group chain length?

No, you either count in the ring or count a substituent coming off of it

What does an R group mean in terms of identifying functional groups?

the remainder of the compound which is usually just carbon and hydrogen atoms

Identify this functional group

alkyl halide

Identify this functional group

Alkene

Identify this functional group

Alkyne

Identify this functional group

Alcohol

Identify this functional group

Ether

Identify this functional group

Thiol

Identify this functional group

Aromatic (or arene)

Identify this functional group

Ketone

Identify this functional group

Aldehyde

Identify this functional group

Carboxylic acid

Identify this functional group

Ester

Identify this functional group

Amide

Identify this functional group

Amine

Identify this branch Alkyl substituent

Isopropyl

Identify this branch Alkyl substituent

sec-Butyl

Identify this branch Alkyl substituent

Isobutyl

Identify this branch Alkyl substituent

tert-Butyl

Identify this branch Alkyl substituent

Isopentyl

Identify this branch Alkyl substituent

Neopentyl

Are gouche interactions favored?

they are more energetically unfavorable than anti interactions due to increased steric strain and decreased orbital overlap

What is a gouche interaction?

a type of steric strain that occurs when two bulky substituents on adjacent carbon atoms in an alkane are oriented in a gauche (60° dihedral angle) conformation

What is steric strain? What does this only really apply to

the increase in potential energy of a molecule due to repulsion between electrons in bulky substituents that are not directly bonded to each other. Only really applies to bulky substituents and not just hydrogens.

What is torsional strain also known as and what is it? When does it only exist?

It is also known as eclipsing strain and it is the increase in potential energy of a molecule due to repulsion between electrons in bonds that do not share an atom. Only exists in eclipsed confirmations and not staggered ones.