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| Organic chemistry |
Study of carbon compounds (not just living cells) |
| Characteristics of organic compounds |
a.) Nonpolar-attractions between molecules are weak 2. Low boiling & melting points 3. High flammability 4.Most or not soluble in water unless a polar group is present |
| Hydrocarbons |
Organic compounds that contain ONLY hydrogen and carbon |
| In organic compounds, every carbon atom ALWAYS has four bonds - true or false? |
TRUE |
| Tetrahedral structure of carbon |
Can be drawn as ball-and-stick model, etc. |
| Alkanes |
Class or family of organic compounds that a.) contain only carbon and hydrogen atoms and b.) ONLY form single bonds |
| Alkanes (examples) |
Many are fuels - methane, ethane, propane and butane |
| Alkanes (structure) |
Contain two, three, four, etc. carbon atoms connected in a CONTINUOUS CHAIN |
| Pent |
5 |
| Hex |
6 |
| Hept |
7 |
| Oct |
8 |
| non |
9 |
| dec |
10 |
| Condensed structural formula |
write each carbon atom & its attached hydrogen atom as a group |
| Alkyl group |
A carbon branch - an alkane that is missing on hydrogen atom |
| Can Alkyl groups exist on their own? |
No, they must be attached to a carbon chain |
| A halogen atom attached to a carbon chain |
a HALO group - Remember the halogen group? |
| Halogen group molecules: |
Fluoro (F), Chloro (CL), Bromo (Br), and Iodo (I) |
| Substituent |
1.) alkane with four or more carbon atoms, 2. atoms can be arranged so that a side or BRANCH or SUBSTITUENT |
| Isomer |
Two compounds - SAME molecular formula but different ARRANGEMENTS of atoms |
| Haloalkane |
Halogen atoms (flourine, bromine, chlorine, iodine) instead of hydrogen (alkyl group) these are halo-alkanes |
| alkanes |
gasoline, diesel fuels, heating oil, mineral oil, petrolatum |
| Alkanes - solubility and density |
nonpolar (insoluble in water) BUT they are soluble with other nonpolar solutes (other alkanes) - Less dense than water (they float) |
| First 4 alkanes |
methane, ethane, propane and butane-are gases at room temperature - used as heating fuels |
| Alkanes have 5-8 carbon atoms |
Pentane, hexane, heptane & octane - are liquids at room temperature, volatile |
| Alkanes with 9-17 carbon atoms |
Kerosene, diesel, & jet fuels -higher boiling points - higher molecular weights |
| Alaknes with 18 or more carbon atoms |
Waxy solids at room temperature-paraffins - coat fruit - petrolatum or Vasline, is a mixture of liquid hydrocarbons |
| Alkanes - melting and boiling |
Lowest melting & boiling of all organic compounds |
| Carbon-carbon bonds - combustion |
Carbon-carbon single bonds are difficult to break-alkanes are the LEAST reactive family BUT they burn readily in oxygen |
| Combustion |
Alkane + O2 ------ CO2 + H2) + energy |
| In alkanes, how are carbon atoms classified? |
Primary-1 degree - carbon is bonded to another carbon - Secondary - 2 degree--carbon has two carbon atoms attached to it - Tertiary - 3rd degree carbon-bonded to three other carbons |
| halogenation of Alkanes (substitution) |
Atoms of a halogen (fluorine, bromine, chlorine, iodine) replace hydrogen atoms - when exposed to light or heated |
| Chlorination |
When the process of HALOGENATION (replacing a hydrogen atom with a halogen-group atom) uses chlorine |
| Bromination |
When halogenation uses bromine |
| Halogenation - compare to hydrogen bonding |
Halogens have 7 valence electrons; therefore they form one bond |
| Functional groups |
compounds react in predictable ways |
| Alkenes |
Functional group - contains a double bond between two adjacent carbon atoms |
| Alkynes |
Contain a triple bond between two adjacent carbon atoms |
| Aromatic compounds |
Contain Benzene - a molecule with a ring of six carbon atoms with one hydrogen atom attached to each carbon atom |
| Aromatic compounds |
Benzene ring |
| Alcohol |
Have a hydroxyl group (-----OH) Oxygen plus carbon equals alcohol! |
| Ethers |
Functional group - one oxygen atom bonded to two carbon atoms |
| Aldehydes & ketones |
Contain carbonyl group C===O (Carbon double-bonded to oxygen |
| Aldehyde |
Caron atom of the carbonyl group is bonded to one carbon & one hydrogen atom |
| Ketone |
Carbonyl group is bonded to two other carbon atoms |
| Amines |
Central atom is nitrogen atom |
| Amines |
Derivatives of ammonia NH3 - carbon atoms replace one, two or three of the hydrogen atoms |
| AmiDDDDe |
Instead of hydroxyl group as in carboxylic acid -- there is a nitrogen group |
| shape of carbon atoms |
tetrahedral |
| combustion - alkanes |
Alkane + O2 ---CO2 + H2O + energy |
| Alcohols |
A class of organic compounds that contains the hydroxyl (--OH) group bonded to a carbon atom |
| Aldehydes |
A class of organic compounds that contains a carbonyl group (C==O) bonded to a least one hydrogen atom |
| Alkanes |
Hydrocarbons containing only single bonds between carbon atoms |
| Alkenes |
Hydrocabons that contain carbon-carbon double bonds (C==C) Hint: Alkenes contains two "e" and they contain two "C" bonds |
| What is the degree of angle for the carbon tetrahedron? |
109.5 |
| Cycloalkanes |
Carbon atoms form a ring or cyclic structure |
| How do you write name of cycloalkane? |
prefix "cyclo" before the alkane name with the same number of carbon atoms |
| What does the IUPAC name indicate in organic molecules? |
It indicates the NUMBER of carbon atoms |
| A continuous alkane |
Carbon atoms are connected on a chain and bonded to hydrogen atomes |
| Sustituents can replace __________ on an alkane |
Sustituents replace hydrogen atoms |
| A Haloalkane contains one or more |
F, CL, Br or I atoms |
| condensed structural formula |
Show arrangement of carbon atom in a molecule but group each carbon with its bonded hydrogen atom |
| halogenation reaction |
A substitution reaction - can occur naturally in light or with heat - halogen atoms replace hydrogen atoms in an alkane |
| line-bond formula |
A type of structural formula that shows only the bonds from carbon to carbon |
| Are organic compounds typically solid at room temperature? |
No, that is more characteristic of inorganic compounds, which also have high melting & boiling points, are soluble & have strong covalent bonds |
| polymers of alkanes - what are they? How do they occur naturally? |
Long-chain molecules that consist of many repeating units of smaller carbon molecules (monomers) Cellulose & starch are polymers of glucose |
| Name two polymers of glucose |
Cellulose & starch |
| Name two polymers of amino acids |
Proteins are polymers of amino acids |
| Synthetic polymers - Ex. |
nonstick Teflon -poly tetra flouro ethylene |
| Aromatic compounds-what is the base? |
Benzene "rings" smells |
| Benzene |
A ring of 6 carbon atoms with one hydrogen atom attached to each carbon |
| Naming aromatic compounds |
ortho (1,2 arrangement) - meta (m) 1,3 arrangement and para (p) is 1,4 arrangement |
| Ortho - di chloro benzene |
1,2 chloro on benzene ring |
| Ortho |
"o-o's" don't go very far from each other 1-2 are not far from each other |
| Meta (m) |
Meta (m) 1,3 arrangment - "a-e" are three steps apart |
| Para (p) |
1,4 (ara) first are separate by a number from the back of the alphabet |
| sulfanation |
"Sulfa saved our nation" sulfa drugs produced by adding sulfur to benzene rings |
| Nitration |
Benzene is heated with nitric acid |
| Halogenation |
(blank) |
| Markovnikov's rule |
(blank) |
| halogenation adds _____ or ______ to form _______ |
Halogenation adds Cl2 or Br2 to form haloalkane |
| Hydorhalogenation adds ______ and _______ to form ________ |
Hydrohalogenation adds HCl, HBr to form haloalkanes |
| Hydrogenation adds ______ to form _____ |
Hydrogenation adds H2 to form Lakanes |
| Hydration adds ______ to form ______ |
Hydration adds H2O to form alcohols |
| Aromatic compounds undergo _________ reactions, because they are stable |
Aromatic compounds undergo SUBSTITUTION reactions such as halogenation, nitration and sulfonation |
| Unsaturated hydrocarbons |
A compound of carbon & hydrogen which contains at least one double or triple bond |
| Cis isomer |
A geometric isomer which simlar gropus are connected on the same side of the double bond |
| Trans isomer |
A geometric isomer in which similar gropus are connected to opposite sides of the double bond in an alkene |
| Alcohol |
A hydroxyl group (--OH) replaces a hydrogen atom in an alkane |
| What makes alcohol in Ohio? |
An --OH group bonded to a carbon atom OR A CARBON CHAIN |
| Chain-chain-chain of fools... |
When naming alcohols, count longest chain CONTAINING the --OH group |
| Phenol |
benzene ring with --OH group |
| ethanol |
ethyl alcohol - intoxicating product - ethene plus water used to make commercial alcohols such as varnishes |
| Phenal is part of essential oil of plants |
such as eugenol (in cloves0 |
| Why is glycerin good in soaps? |
it is a trhydroxy alcohol - the presence of polar --OH groups makes it strongly attracted to water, so that it is useful as a skin softener |
| Thiols |
SMell bad - if you had to smell someone thigh - all over -- you'd stink - oysters, cheddar chees |
| What is on the thiols? |
an --SH group |
| Ethers |
Have OXYGEN atom attached by SINGLE BONDS - to two carbon groups |
| ether (structure) |
"Either or" the oxygen is in the middler, the carbon is either on one side or the other, |
| ether (examples) |
ethers are anesthetics - inhibit pain signals to the brain |
| Cyclic ethers (example) |
Dioxin-formed during forest fires - is highly toxic |
| Cyclic ethers |
have an oxygen atom within a carbon ring Di-oxin |
| Alcohol |
--OH group replaces a hydrogen atom |
| Phenol |
Hydroxyl --OH group is attached to aromatic rings |
| Thiols |
family of organic compounds containing sulfhydryl --SH group (similar to alcohol but --SH group takes the place of an --OH group |
| Who wants to smell my thigh--all? |
YECCH--skunks, onions, and garlic have THIOL |
| Primary alcohol |
One alkyl group (CH3) attched to carbon atom |
| Secondary alcohol |
2 degrees - has two Alkyl (CH3) group attached |
| Tertiary 3 degree |
Has three alkyl (CH3) groupps attached to it |
| Phenols |
Benzene ring bonded to hydroxyl --OH group |
| Phenol - Beano-drunko |
benzene (beano) with hydroxyl group |
| T |
(blank) |
| ester |
H in carboxyl group is replaced with an alkyl group |
| Esterification |
Carboxylic acid and alcohol react (in presence of acid catalyst) to produce an ester |
| Ester (examples) |
Aspirin, oil of wintergreen |
| esters - fruits & flowers |
give them their fragrance |
| lipids |
biomolecules that contain fatty acids or steroid nucleus |
| what type of lipid does NOT contain fatty acids? |
steroids |
| Fatty acid formulas |
Long line-bond formulas (remember video of guy holding long model) |
| Do fatty acids contain carboxylic acids? |
Yes --they are composed of |
| Fatty acid formulas (condensed) |
Indicate # of carbon atoms, # of double bonds & the position of the double bonds |
| Saturated fatty acids (naturally occuring) |
SINGLE C-C bonds; fit closely together, strong attraction between fatty acid chains MEATS |
| UNsaturated fatty acids |
Kinky, loose--liquid-low melting point |
| Prostaglandins - weird name, weird shape |
trans double bond on carbon 13 - look like long "U's" |
| Fatty ACID** |
a long carbon chain with CARBOXYLIC ACID group at one en |
| Prostaglandins- what number is so associated with them that they are sometimes called ____ |
20 - they have 20 carbons - called "eicos" - greek word for 20 |
| What is structure of most prostoglandins? |
hydroxyl group on cabron 11&15 - trans double bond on carbon 13 |
| What do prostaglandins do? |
increase blood pressure, cause pain & inflammation in injured tissue |
| Esters |
fatty acid plus long-chain alcohol |
| Triacylglycerols |
Fatty acids stored in body |
| How are triacylglycerols formed? |
"tri" three acyl (the fatty acid?) plus glycerol ( |
| hydrogenation |
ADDITION REACTION - Unsaturated fats with Carbon-carbon double bonds to single bonds |
| traicylglycerols - how are they formed? |
through esterification - hydroxyl groups ract with carboxyl groups of fatty acids |
| Glycerophospholipid - Structure (think LAB-stuff floating in water) |
POLAR head (amino alcohol) with NONPOLAR fatty acid chains - |
| Glycerophospholipid - examples (think brainy - the word is so long you have to be brainy to find it) |
Lecithin - in brain & nerve tissues - egg yolks, wheat germ & yeast |
| SPHINGOLIPIDS |
found in nerve cells |
| sphingolipids |
"SPHinx" has a big head - nerves are in your head |
| sphingomyelin |
white matter of myelin sheath--surrounding nerve cells |
| glycosphingolipids & cerebroside |
sphingolipids that have sugars (glyco--stupid) |
| gangliosides |
"GANG UP - tay-sachs disease-accumulates in body |
| steriod |
"steering wheels" - FOUR rings - 3 cyclohexane plus 1 cyclopentane |
| Do steroids contain fatty acids? |
NO - and they're non-polar |
mr. charles11
