OChem Test 1

What is organic chemistry

the study of carbon containing molecules

What happens during a reaction?

Molecules collide and bonds are formed and or broken

_____ and _______ reside in the nucleus

Protons (+1) and neutrons (neutral) reside in the nucleus

______ reside in the orbitals outside the nuceus

Electrons (-1)

how can one determine the number of valence electrons?

by looking at the periodic table

_____ are pairs of electrons that are shared between atoms

covalent bonds

As energy increases, stability ______

decreases

As energy decreases, stability _______

increases

what are the atoms that are most commonly bonded with carbon?

hydrogen, nitrogen, oxygen, halogens

Cabon’s bonding is _________

tetravalent

Nitrogen’s bonding is _______

Oxygen’s bonding is

divalent

Halogen’s bonding is ______

monovalent

What charge is this?

negative carbon

carboanion

what charge is this?

no charge. neutral carbon.

what charge is this

positive

carbocation

what charge is this?

negative

what charge is this?

none.

this is neutral nitrogen

What charge is this?

positive

what charge is this?

negative

what charge is this

neutral oxygen

what is the charge

positive

what is the charge

negative

what charge is this

neutral halogen

What is the formula that we can use to calculate formal charge?

Formal charge= # of VE - #LP+#B

or the way i used to remember it it was

VE-NB+CE (venice)

What is electronegativity?

How strongly an atom attracts shared electrons

electronegativity increases moving toward fluorine

What are the three types of bonds?

Covalent, Polar Covalent, Ionic

What type of bond shares electrons between two atoms? Electronegativity is less than 1

Covalent bond

What type of bond shares electrons between two atoms with electronegativity above one?

polar covalent bond

What type of bond is where electrons are not shard and the two atoms have electronegativity difference of more than 1.7? The more electronegative atom owns the electrons

Ionic bond

What happens to polarity of the bond as electronegativity increases?

it is more polar

Electrons behave as both _____ and _____

waves and particles

We should think of an atomic orbital of a cloud of ________. _____ increases with electronegativity

electron density

A covalent bond occurs when atomic orbitals ____

overlap

Wjhat are the two theories for describing atomic orbital overlap?

valence bond theory and molecular orbital theory

only _____________ results in a bond

constructive interference

The more s character in the orbital, the ____ and the _____ the bond

stronger and shorter

What is the steric number?

number of hybrid orbitals= number of bonds + number of lone pairs

if the steric number is 4, then it is ….

sp3

The steric number is 2 and the hybridization is sp. What is the Electron Domain Geometry? What is the bond angle?

linear

180 degrees

the steric number is 3 and the hybridization is sp2. What is the electron domain geometry? What is the bond angle?

trigonal planar.

120 degrees

The steric number is 4 and the hybridization is sp3. What is the electon domain geometry? What is the bond angle?

tetrahedral

~109.5 degrees

lone pairs lead to a slightly ___ bond angle which changes ______

smaller

molecular geometry (not electron geometry)

If you have polar bonds, does that mean the molecule is polar

NO

What are three types of intermolecular forces?

dispersion forces (london dispersion forces)

dipole-dipole

hydrogen bonding

What intermolecular force is present in everything?

dispersion forces (london dispersion forces)

What intermolecular force involves polar moelcules?

dipole-dipole

what intermolecular force is the strongest but still weaker than a covalent bond

hydrogen bond

Dipole-dipole forces result when polar molecules line up their _____ charges

opposite

compared to weaker IMFs, molecules exhbititing ______ attractions will have a higher melting and boiling point

dipole-dipole

Hydrogen bonding is the attractive force between a H bonded to an ______ and a _____

electronegative atom (N,O,F) and a lone pair of electrons

The greater the _______ of a molecule, the more temporary dipole attractions are possible

surface area

what is true of branching as it pertains to surface area and boiling pt

more branching leads to less surface area and lower boiling point

like dissolves ____

like

How does soap work?

oil molecules are nonpolar.

soap molecules organize into micelles in water, which form a nonpolar interior and carry dirt away.

What is true of the postitioning of solid and hatched lines in 3D drawings?

they must be near each other and not seperate

name the functional group and why

alkyl halide

carbon bonded with a halogen (Cl, Br, I , F)

What functional group and why

Alkene

carbon to carbon double bond

what functional group is this and why

alkyne

triple bond between carbons

What functional group is this and why

alcohol

because of the OH group

What functional group is this

Amine

nitrogen containing

The spreading of electrons called ______ is a stabilizing factor. it is often referred to as _________

delocalization
resonance stabilization

Should you ever break a single bond when making a resonance structure

FUCK NOOOO

define allylic lone pairs.

when a compound contains a carbon-carbon double bond.

what is this

vinylic positions

What is this

allylic positions

What are the five general bonding patterns in which resonance occurs?

1) an allylic lone pair

2) an allylic carbocation

3) a lone pair adjacent to C+

4) A pi bond between two atoms of differing electronegativity

5) conjugated pi bonds in a ring

What is this

allylic carbocation

what is this

allylic lone pairs

What are the rules for importance in resonence structures

-the most significant contributors have the greatest number of filled octets

-the fewer the formal, the more significant

-a structure with a few negative charge on a more electronegative atom will be more significant (and vice versa)

-When both have stable “good” Lewis structures, they contribute equally

A structure with a negative charge on the more electronegative atom will be _____ significant

more

(negative charge on the carbon will be bad news)

A structure with a positive charge on the less electronegative atom will be ____ signfiicant

more

positive charge on oxygen is bad

What happens when a lone pair participates in resonence?

it will occupy a p orbital rather from a hybridized orbital

When an atom possesses a pi bond and a lone pair, what will happen pertaining to resonance?

they will generally not participate in resonance

_____ donate a proton (acids or bases)

acids

_____ accept a proton (acids or bases)

bases

A _______ results when a base accepts a protein

conjugate acid

A ____ results when an acid gives up a protein

conjugate base

what is this? how will we move things?

allylic lone pair

What is this? How can we move things?

Allylic carbocation

What is this? How can we expect it to act?

Lone pair adjacent to C+

what is this? How might we move things?

pi bond between two atoms of differing electronegativity.

what type of structure is this and how do you solve it?

Conjugated pi bonds enclosed in a ring

What is the pka of HBr and HCl?

<0

What is the pka of H3O+ or

~0

What is the pka of (carboxylic)

~3-5

What is the pka of
(protonated amine)

~10

what is the general pka of water

~14

what is the general pka of alcohol?

~15

what is the general pka of an alkyne?

~25

what is the general pka of an amine?

~40

What does equilibrium favor?

the weaker acid and the weaker base

What uses numerical data to compare how strong acids are?

Quantitative strength analysis

if Ka <1 the reaction is _____ favored

reactant favored and strong acid

if ka > 1 the reaction is _____ favored and a ____ acid

product favored and weak acid

the ____ the acid the more stable the conjugate base

STRONGER

conjugate base is whatever is remaining after we lose a hydrogen

What are the factors that stabilize a negative charge?

ARIO (A really interesting occasion) (i had a rather interesting day today)

-the type of atom that carries the charge

-resonance

-inductive effects

-the type of orbital where the charge resides

When moving down a column, the ____ is the most important factor. What does this aspect tell us?

size tells us that the larger the atom, the more stable a negative charge will be. Size increases as you move down the periodic table

When moving across rows (periods), ______ is the most important factor. What is true here?

electronegativity

the more electronegative atom will better stabilize the negative charge.

_____ stabilizes a negative charge by spreading it out across multiple atoms

resonance