Organic Chem Memorization Test 1

alkyl halide (haloalkane)

alcohol

ether

carbonyl

amine

thiol

sulfide

disulfide

aldehyde

ketone

carboxylic acid

ester

thioester

amide

acid chloride

Methane

1-C

Ethane

2-C

Propane

3-C

Butane

4-C

Pentane

5-C

Hexane

6-C

Heptane

7-C

Octane

8-C

Nonane

9-C

Decane

10-C

staggered

most stable, high distance between atoms

eclipsed

high reactivity, high energy, minimal distance between atoms.

torsional strain

extra energy of eclipsed conformer over staggered conformer

H←→H eclipsed (cause and kJ/mol)

Torsional strain, 4.0 kJ/mol

H←→CH₃ eclipsed (cause and kJ/mol)

Torsional Strain, 6.0 kJ/mol

CH₃←→CH₃ gauche (cause and kJ/mol)

Steric Strain, 3.8 kJ/mol

CH₃←→CH₃ eclipsed (cause and kJ/mol)

Both torsional and steric, 11.0 kJ/mol

anti-staggered conformation

the two largest or bulkiest substituents are 180 degrees away from each other. 0 kJ/mol

gauche conformation

the two largest or most bulky substituents are 60 degrees from each other, creating steric strain

steric strain

increase in a molecule's energy caused by repulsive forces between non-bonded atoms or bulky groups that are forced closer together than their van der Waals radii allow

syn eclipsed conformation

Least stable conformation, the two largest or bulkiest substituents are lined up as close as possible (pointing in the exact same direction)

Principal Quantam number (n)

describes the energy level (shell)

1 orbital - n=1

2 orbitals - n=2

Angular momentum quantam number (l)

describes the shape of the orbital. Ranges from 0 to (n-1).

0 = s orbital, 1 = p orbital, 2 = d orbital 3 = f orbital

magnetic quantam number (m_l)

3-D orientation of EACH INDIVIDUAL ORBITAL. There will be a m_l value for ALL values of l. For example, if l = 2, there will be a value for m_l=0, m_l=1, m_l=2.

shape of p orbitals

dumbbell shaped

Nonpolar covalent bonds electronegativity difference

Lower than 0.5

Polar covalent bonds electronegativity difference

Ranging from 0.5 to 2

ionic bonds covalent bonds electronegativity difference

2 or higher

Resonance structures become possible when what appears (2 things)

lone pairs OR pi bonds

Bronsted Lowry definition

Acids donate H+ (protons), bases accept H+ (protons)

Acid/Base Reactions always favor which side?

whichever side gives the weakest acid or base.

Lewis definition

Acids are LP acceptors, bases are LP donors. Acids must have a COMPLETELY available orbital. Lewis bases will always have LP electrons available to donate

What makes a molecule hydrophilic?

OH and NH groups (per every 4 carbons at least). Compounds containing polar bonds and lone pairs also tend to be hydrophilic.

alkenes

have at laest one carbon-carbon double bond

alkyne

have at least one carbon-carbon triple bond

Arenes

have alternating single and double carbon-carbon bonds forming a ring.

alkanes

have only single bonded carbon and hydrogen atoms

alkane formula

C_nH_2n+2

Which alkanes cannot have any isomers?

methane, ethane, and propane. (not enough carbons)

constitutional (structural) isomers

have the exact same number and type of atoms, just arranged differently.

alkyl group

Formed when one hydrogen atom is removed from an alkane.

n-alkyl group

this group will ALWAYS have it’s disconnected hydrogen be at one of the ends of the molecule.

tertiary carbon/quaternary carbon

3 carbon bonds/4 carbon bonds

Why is a quaternary alkyl group impossible?

quatenary carbons have 4 carbon bonds, and due to alkyl groups having one available bond (disconnect), it cannot get a 4th carbon bond.

Boiling and melting points of alkanes

Increase as size of alkane increases, due to increase in dispersion forces.

Branching does what to an alkane’s boiling point?

Lowers it, because it reduces the interface (forces) between molecules

conformations

different arrangements of atoms that come from bond rotation

Conformers

atoms that are involved in molecules that have conformations

iso (for alkyl groups)

anything can be an iso if the last carbon on the branch is moved to the main part of the branch.

Sec-butyl

a four-carbon Butyl group where attachment to the main molecular chain occurs at a secondary carbon atom

tert-butyl

central carbon atom is bonded to three methyl groups

pKa

(-log(Ka)) Low pKa = strong acid. High pKa = weak acid.

Ka

acid constant. High Ka = strong acid, low Ka = weak acid (partial dissociation)