Naming Organic Compounds (copy)

Hydrocarbon

organic compound consisting of only C and H

Examples of hydrocarbons

methane, ethane, benzene

Each Carbon can have how many bonds?

4 single bond counts as 1 double bond counts as 2 triple bond counts as 3

Which bond(s) rotate freely?

single bonds (sigma)

Which bond(s) do not rotate freely?

double & triple bonds (due to pi bonds within them)

What are the 3 different structures of the C skeleton?

branched, linear, & cyclic (rings)

A Carbon atom single-bonded to another C atom has how many H atoms?

3

A Carbon atom single-bonded to two other C atoms (in the middle) gets how many H atoms?

2

A double-bonded C atom gets how many H atoms?

2, treated as if bonded to 2 atoms

A carbon atom single-bonded to three other atoms gets how many H atoms?

1

A Carbon atom single-bonded to four other atoms gets how many H atoms?

0, already has its 4 bonds (can’t bond anymore)

Which hydrocarbon has the suffix ane?

alkane (CnH2n+2)

Hydrocarbons that contain only single bonds & are referred to as saturated (no multiple bonds) hydrocarbons:

alkanes

Shape & Hybridization of C in alkanes:

tetrahedral & sp3

Root for 1 C atom in chain

meth

Root for 2 C atoms in chain

eth

Root for 3 C atoms in chain:

prop

Root for 4 C atoms in chain:

but

Root for 5 C atoms in chain:

pent

Root for 6 C atoms in chain:

hex

Root for 7 C atoms in chain:

hept

Root for 8 C atoms in chain:

oct

Root for 9 C atoms in chain:

non

Root for 10 C atoms in chain:

dec

Each prefix identifies what?

a group attached to the main chain along w it’s position

Which # rings are the most stable? cycloalkanes

5 & 6 member rings

Cycloalkanes area member of what subfamily?

alkane subfamily

Which # rings are strained? cycloalkanes

3 & 4 member rings

constitutional/structural isomers have the same molecular formula but different what?

different arrangement of the bonded atoms

structural isomers

different compounds w/ different properties

What happens if isomers contain the same functional groups?

their properties will be similar

structural isomers of C5H12:

pentane 2-methylbutane 2,2-dimethylpropane

more spherical molecules have more or less I.F? why?

less I.F because of less surface area & don’t become entangled as readily

alkene (CnH2n)

a hydrocarbon that contains a carbon-carbon double bond & referred to at unsaturated hydrocarbons

rotation is restricted around what bonds?

double bonds

shape & hybridization of C in a double bond:

trigonal planar, sp2

e^- rich & act as functional group

alkene & alkynes

examples of alkenes

C3H6 C4H8 C5H10

Naming alkenes:

1. main chain must contain both C atoms w/ the double bond.

2. the chain is numbered from the end closer to the C=C bond & position of bong is indicated by the # of 1st C atom in it

cis

same

trans

opposite

what must be specified as prefix when applicable?

cis- or trans-

geometrical isomers:

cis-trans isomers; have different physical properties

Hydrocarbon that contain at least one C-C triple bond

alkynes

referrred to as unsaturated hydrocarbons

alkynes (CnH2n-2)

rotation is stricter around which part of alkynes

it’s triple bonds

shape & hybridization of C in a triple bond:

linear & sp

So alkynes have trans- cis- (geometric isomerism)?

no

example of alkyne

ethyne (H-C=-C-H)

aromatic hydrocarbons

cyclic molecules with delocalized pi e^- s

drawn as alternating double & single bonds

functional groups determine:

physical properties & chemical reactivity

define regions of high & low e^- density

functional groups affect what?

polarity of a compound, thus determines types of I.F present

consist of a carbon bounded to an -OH group

alcohols

alcohols have high or low mp & bp?

high since they can form hydrogen bonds between their molecules

contain a halogen atom bonded to carbon

haloalkanes

contains a N atom, weak bases, viewed as derivatives of NH3

amines

amines 3 general types:

Primary (1°)= NRH2 Secondary(2°)=NR2H Tertiary(3°)=NR3

which general type(s) of amine group can form H bonds?

primary & secondary

part of aldehyde, ketone, carboxylic acid, ester, & amide functional groups:

carbonyl group

carbonyl group have what type of bond?

C=O double bond

The C=O bond in carbonyl groups have what partial charges on its molecules? polar or nonpolar?

partial + charge on C & partial - charge in O

e^- rich & highly polar

examples of aldehydes:

methanal, ethanal

examples of ketones:

2-propanone (acetone), 2-Butanone

contain the functional group -COOH & what are examples

carboxylic acid ex: methanoic acid (formic acid), butanoic acid

amide functional group:

R-C=O-N

ester

part of carbonyl group, O=C-O

ion-dipole forces

interaction between an ion (full charge) & a polar molecule (partial charge) ex: CaBr2 & H2O (polar)

electrostatic interaction

dissociation occurs with:

ionic compounds strong acids & bases

Hydrogen Bond

the forces that involved an H bound to F,O, or N directly & another dipole w/ F,O or N

high bp & mp

attracted directly to the lone pair of the N,O,F

examples of Hydrogen bonds:

H2O, NH3

Dipole-Dipole Forces

the attraction between two dipoles of separate (polar) molecules

more orderly in solid form

dipoles aim in the general direction of opposite dipole

electrostatic interaction

ex: HBr & HCl; CH3F & HCl

Dipole-Induced-Dipole:

-involves polar molecule & np molecule -polar molec is the “electric field” & np molec is “induced” (causing e^- density to shift) to have temporary dipole -ex: H2O & O2 (a dipole & O2 is np)

London Dispersion Forces

-strongest forces when 2 np molecules interact -weakest force overall -temporary instantaneous interaction -constantly interacting & breaking Present in ALL molec & ions

What intermolecular force is responsible for the condenser states or np molecules?

London Forces ex: octane, Cl2, Ar, N2

What happens regarding London dispersion forces as molecules get larger?

there are more dispersion forces per molecule, causing an increase in bp

Polarizability

the ease w/ which it’s electron cloud is distorted

• large species more polarizable; bottom left of periodic is most

What is the relationship for surface area w/ London forces?

the more surface area, the more points of contact for dispersion forces to occur

What is the relationship between intermolecular forces & bp?

the higher the bp the stronger the intermolecular force & viscosity, lower the v.p

What is the relationship between I.Fs & mp&bp?

As I.Fs get stronger, bp & mp increase

What is the relationship between I.Fs & vapor pressure?

the stronger the I.Fs, the lower the v.p

What is the relationship between I.Fs & viscosity?

The stronger the I.F, the higher the viscosity

The relationship between I.F & surface tension of a liquid?

the stronger the I.Fs of the liquid, the higher the surface tension

Relationship between I.F & solubility?

The stronger the I.F between the solute & solvent, the greater the solubility of the solute in the solvent.

Relationship between ion-dipole & charge density?

The highest c.d will form strongest ion-dipole w/ water.

Rules for charge density:

1. higher the charge # (-2,+2)

2. size (smaller the stronger;cations usually)

Rank solid molec, liquid molec, and gas mole in order of lowest to highest potential energy

gas (lowest potential), liquid (intermediate), solid( high potential)

What is the relationship between kinetic and potential energy?

the higher the kinetic, the lower the potential

What does potential energy depend on?

charge & distance

What do potential and kinetic energy interactions explain?

phase changes

What is polarizability? What has more polarizability?

the ease w/ which it’s e^- cloud is distorted

large molecules/anions have more polarizability

Polarizability trends:

Increase as you go to bottom left of periodic table because atomic size increases & large e^- clouds distort more easily

Polarizability & I.Fs:

The higher the polarizability, the large the molecule (larger surface area) so more points of contact for dispersion forces to occur

What is true about ionic bonds?

-formed between metals and nonmetals -e^- are transferred not shared

What is true about metallic bonding?

Within a solid piece of metal, the positive nucleus of each atom in a metallic solid is attracted to the electrons of the atoms that surround it

dispersion forces depend on:

total mass of species, the more mass the more interaction. If only C-H molecules are present count the # of C’s. The molecules with more amount of Cs have largest dispersion force. If 2 molecules have same amount, see which one will be linear structure vs branched (linear takes up more room so stronger).

What is true regarding ethanol?

-polar -contain covalent intramolecular bonds -has dispersion forces

What is true regarding Dimethyl Ether?

-polar -has dispersion forces

Structural Isomers Conditions:

-have different arrangement of same atoms -have same molecular formula have nonsuperimposable images

colligative properties depend on:

the conc. of solute molec (or ions) /# of partials dissolved

NOT IDENTITY OF SOLUTE

pi-bonding:

-doesn’t always result in a side-on overlap

-pi bonding does not always result in cis-trans isomers

-occurs most often in short bonds w/ the atom’s p orbitals

-does not always result in an e^- rich and polar region of a molec