Organic Chemistry

CHEM*1040

Constitutional/structural isomers

structures with the SAME molecular formula but DIFFERENT arrangement of atoms

Saturated hydrocarbons

hydrocarbons containing ONLY SINGLE bonds between carbon atoms

T or F: saturated hydrocarbons can be cyclic or acyclic

True

Unsaturated hydrocarbons

hydrocarbons that contain double or triple bonds between carbon atoms

Aromatic hydrocarbons

hydrocarbons containing benzene rings or similar features

Alkane

Substitution reaction

Part of the reacting molecule is substituted for an H atom on a hydrocarbon/hydrocarbon group

Alkene

Primary

1 carbon attached directly to focal point

secondary

2 carbons attached directly to focal point

tertiary

3 carbons attached directly to focal point

quaternary

4 carbons attached directly to focal point

Most chemical reactions involving organic compounds involve a change in __________

functional group

alkyl halide (haloalkane)

-C-O-C-

ether

-C-OH-

alcohol

aldehyde

ketone

amine

carboxylic acid

amide

What is the general formula of alkanes?

CnH2n + 2

CH3-

methyl

CH3CH2-

ethyl

CH3CH2CH2-

propyl

isopropyl

t-butyl

What is the general formula of cycloalkanes?

CnH2n

T or F: alkenes and alkynes are unsaturated hydrocarbons

true

Rotation around C-C dbl bond is restricted due to side-to-side overlap of ____ orbitals to form ___ bond

p, pi

o-xylene (left)

m-xylene (center)

p-xylene (right)

Organic halides are compounds with one or more ______ attached to a carbon

halogens

Ethers are compounds having an ______ atom bonded to two _______ atoms

oxygen, hydrocarbon

Ethers are treated as ________

substituents

CH3O-

methoxy

CH3CH2-

ethoxy

Alcohols possess one oxygen atom bearing an _______ and a ___________

H, hydrocarbon atom

Amines are compounds with a _________ attached to 1-3 hydrocarbon atoms

nitrogen

Aldehydes and ketones both contain a ____________

carbonyl group

Carboxylic acids and derivatives contain _______

acyl group

T or F: In an acyl group, A = H

False; A does not equal H

Carboxylic acid name ending

anoic

Ester/salt name ending

anoate

Amide name ending

-anamide

alcohol name ending

-anol

amine name ending

-anamine

aldehyde name ending

-anal

Structural isomers

differing atom attachments

What type of structural isomer is this?

skeletal isomer

What type of structural isomer is this?

positional

What type of structural isomer is this?

functional group

Stereoisomers

SAME atom attachments DIFFERENT arrangements in space

Geometric isomers

cis and trans isomers

cis or trans?

trans

cis or trans?

cis

Chiral compounds

optically active compounds that can interact (rotate the plane) with plane polarized light

Plane polarized light consists of __________

waves that vibrate in one plane

Dextrorotatory

or +
plane rotated clockwise

Levorotatory

or -
plane rotated counterclockwise

Chiral compounds cannot be ________ on its mirror image

superimposed

achiral

not optically active

Most common type of chiral compounds include a carbon bonded to ______ different groups

four

Asymmetric carbon/chiral center

carbon atom attached to 4 different groups

Enantiomer

pair of non-superimposable mirror images

Enantiomers have identical __________ properties

physical (MP, BP, densities, solubilities)

Enantiomers rotate place polarized light in _________ directions

opposite

LDF

small electronegativity difference
very small dipole moments
non-polar

Dipole-dipole

large electronegativity difference
polar bonds

Hydrogen bonding

very large electronegativity difference
Hydrogen attached to something other than carbon
very strong intermolecular attractions

What do boiling/melting points reflect?

How strong intermolecular forces are

Water is ________ and has ___________

polar, hydrogen bonding

What is the order of water solubility?

H-bonding > dipole-dipole > LDF

If the functional group remains the same but the number of carbons increase the amount of LDF forces _______

increase

If LDF increases, water solubility of a compound would ________

decrease

The most common attacking agents are

electrophilic agents
nucleophilic agents
free radicals

Electrophilic agents

+ve species (H+) wanting to accept an electron pair from a pi bond

Nucleophilic agents

-ve species (OH-, Br-, CN-) OR neutral species that has a FREE PAIR of e-
wants to donate e- to +ve CARBON

free radicals

neutral species possessing single unpaired electron

Reaction intermediates

free radicals
anions
cations (carbocation)

Free radical halogenation
- initiated with UV light
Works when X=Cl, Br

electrophilic addition
- pi bond not as strong as sigma bond

What is the 2 step process for electrophilic addition?

1. electrophilic agent attaches to one of carbons involved in dbl bond producing a carbocation as an intermediate
2. nucleophilic agent attaches to carbocation
Result: A+ and B- add to carbons in dbl bonds and no pi bonds left

Hydrogenation

What is the process of hydrogenation?

H2 adds to a pi bond in the presence of an appropriate catalyst (Pt, Pd, Ni); added simultaneously to same side of dbl bond C

Nitration (aromatic substitution)

Halogenation (aromatic substitution)

What catalysts are required for aromatic substitution?

H2SO4
FeCl3
FeBr3

oxidation

Oxidation reactions of alcohols require ______ or ___________ under acidic conditions (H+)

K2Cr2O7, Na2Cr2O7

The carbon-oxygen bond of a carbonyl has:

very large dipole
pie bond with loosely held electrons

Reduction

Reduction of aldehydes/ketones can also be carried out with ______ or _______

NaBH4, LiAlH4

Nucleophilic Addition

In nucleophilic addition, the +ve H adds to the ________ of the carbonyl and the -ve OH/OCH3 adds to the _________ of the carbonyl

oxygen, carbon

Esters of carboxylic acids can be prepared by heating a mixture of _______ and _______ in the presence of an acid catalyst such as __________

carboxylic acid, alcohol, H2SO4

Distillation

Removing either water or ester

Is the order of acidity increasing or decreasing?

decreasinga

An organic compound can behave as a base if it has ....

a free pair of e- that it can donate a H+