Intro to Organic Chemistry

Pretty much most fun you’ll ever have

What’s Different about Chem II?

• Notes are important!

• Lots of practice, groups, board work

• less “busy work”

• longer labs, more dangerous

• subject is relevant to everyday life

• no math

• lots of stories-yours & mine

Classification thing

Classify each of the following broad groups into 2 sub-groups:

Students in this class

BJHS Teachers

In the olden days (early 1800’s)

• Everything in the world was classified into 2 groups

• What do you think they were called?

• Yep! – Living and Nonliving

• Now called Organic and Inorganic

• Organic originally referred to

1. part of something living or dead or

2. a substance produced by something living or dead

*A new def is coming later

• Everything classified as organic had a special quality scientists called

• The Vital Force• Def: a special (mythical) characteristic of

all organic things

• Ex: Baywatch story

• http://www.youtube.com/watch?v=lqNXE07fKuw

• Big problem back then: there was no way to create vital force compounds in the lab!

• BUT, in the early 1800’s, 2 events changed chemistry forever. . . . . . . . .

The 1st one– 1. 1828-German chemist named Friedrich Wohler accidentally

produced urea in the lab.

– Don’t write this: Wohler, Friedrich (1800-1882), a German chemist. He was the first to create an organic substance from inorganic chemicals; in 1828 he heated ammonium cyanate, an inorganic compound, and created urea, a compound found in animal urine. Thus he disproved the belief that organic substances could be formed only in living things. Wohler experimented with almost every chemical element known in his day. He isolated the elements aluminum and beryllium, and discovered calcium carbide.

– He looks so happy

– Note-Urea is a constituent of urine, but the 2 are not the same

• What did Wohler do?

• NH4Cl + AgNCO --> NH4NCO -->NH2CONH2 + AgCl

• What’s weird about this equation?• Joke #1http://chemistry.about.com/od/moleculescompounds/ig/Molecules-with-Strange-Names/Lord of the Carbon Rings• http://www.youtube.com/watch?v

=BDXJThYw4_4• When Wohler presented his findings people

laughed at him-he died sad, ugly, and alone

Amazing info on urea• When proteins are metabolized, N (nitrogen) compds are produced

• But N compds can’t be stored in the body• They must be excreted in a nontoxic & HOH-soluble form• http://www.youtube.com/watch?v=aBVKaTotKBk• NH3 is one possibility, it’s soluble, but it’s also toxic to

humans. (not toxic to snakes & birds)

• So, we excrete N compds as urea-it’s both soluble and nontoxic :)

• Fun urine stories • http://www.youtube.com/watch?v=4U_xmfSwYSw&feature=

PlayList&p=7CBCB29FD596FD12&index=5• Fish not supposed to go there. . .

http://www.youtube.com/watch?v=oDu1E4EndJw

• The 2nd One (one what?) 1845-Herman Kolbe synthesized

trichloroacetic acid (an organic thing) from inorganic substances-again creating the a vital force compound!

• Structure?

• Uses?

• Eventually, chemists made lots of vital force compounds-today there are millions

• Here’s an ex of something created in the lab that’s not even found in nature!

• CH4 + Cl2 CHCl3 + CCl4

• methane + chlorine chloroform + carbon tetrachloride

• The products (things after the arrows) aren’t found in nature-that’s

significant b/c things like this had never been made!

• There are even patents on some life forms-ex: oil-eating bacteria

Let’s talk about methane

• Methane-CH4 also called swamp/marsh gas• Also on other planets• http://videos.howstuffworks.com/discovery/31001-

methane-discovery-on-distant-planet-video.htm 2 min• methane stories, gas detector, church, etc.• apples give off methane, that’s why they’re not stored with

nanners at Kroger-they would ripen too fast

• http://www.youtube.com/watch?v=Oh-1wOSTiP0 2 min

• The methane molecule has a pyramid or tetrahedral shape

•

• Electrons (and H’s) get as far away as possible from each other

Methane & the Bermuda Triangle• Methane Gas Hydrates

This theory appears to hold promise for at least some of the disappearances in the Bermuda Triangle. Scientists at Cardiff University have discovered the presence of large concentrations of methane gas trapped in the ocean floor. This gas is due to dying and decomposing sea organisms. The sediment contains bacteria that produce methane, which accumulates as super concentrated methane ice, called gas hydrates. The layer of ice traps the methane gas, and scientists are studying it as a potential energy source.

• Image courtesy Office of Naval Research

•Within seconds of a methane gas pocket rupturing, the gas surges up and erupts on the surface without warning. If a ship is in the area of the blowout, the water beneath it would suddenly become much less dense. The vessel could sink and sediment could quickly cover it as it settles onto the sea floor. Even planes flying overhead could catch fire during such a blowout. Although he doesn't agree with the methane hydrate theory as an explanation for the Bermuda Triangle, Bill Dillon, a research geologist with the United States Geological Survey said that, "On several occasions, oil drilling rigs have sunk as the result of [methane] gas escape."

• Simulation http://www.youtube.com/watch?v=DkIIMEVnNDg&feature=PlayList&p=4BBEE997F92D7079&playnext=1&playnext_from=PL&index=7 3 min

Cows and methane

• Cows excrete methane• methane depletes the ozone layer• So, are cows are bad? maybe• http://www.youtube.com/watch?

v=zbKRSYAuSNg 4 min• Our govt comes to the rescue! The Ruminant Livestock

Methane Program is formed-consuming millions of taxpayer dollars in the study of reducing bovine methane emissions

• http://videos.howstuffworks.com/planet-green/33432-stuff-happens-wheres-the-beef-video.htm 4 min

  

  

New Def of Organic• Obviously, the old def of organic needed to

be changed• New def: organic things contain Carbon• BUT. . . . . • not all carbon compds are organic

– ex: CO (carbon monoxide)– CO2 (carbon dioxide)– CO3’s (carbonates) – CN’s (cyanides)

Forms of Carbon

• Diamond-has a bunch of C’s bonded together with very strong and tight bonds

• http://www.youtube.com/watch?v=_0UOB50Otok

• Graphite-has strong planar bonds, but weaker inside bonds-molecules slide easily

• Q: are there more organic compounds or inorganic compounds in the world?

• A: Organic!

• Q: why?

• A: Reason #1-the C atom is very versatile!

• Let’s look at it

The Carbon Atom

• Atomic # =6

• # electrons = 6

• # neutrons = 6

• 666=and all life is based on carbon

• C has 4 valence electrons-what does this mean?

• electron configuration of carbon

Carbon cont’d

• C would like to gain or lose 4 e-s, but that’s unlikely

• Looking at the EN (?) of C, it’s kind of in the middle-has no strong desire to give up or gain e-s

• If C stayed like this, it wouldn’t bond w/anything

• So, it decides to hybridize!

Orbital Hybridization of C (this happens in methane)

• Instead of the normal 1s2 2s2 2p2 configuration, Carbon hybridizes into 4 sp3 orbitals

• draw these w/arrows• each sp3 orbital contains 1 electron, and it’s easy for H atoms

to bond w/these single e-s

• Remember this?

• Balloons demo-to show orbital hybridization in methane • http://www.youtube.com/watch?v=DrGRTtdJgoo

Bond #’s in Organic Compds

• 8 is the happy number, but 2 is also OK• CHONPS halogens• don’t forget your diatomics!• Draw these:

NH3 CH2O C3H8

H2O HCl HCN

Let’s build them

Organic Families

• Alkanes• Alkyl halides• Alkynes• Alkenes• Alcohols• Aromatics• Aldehydes• Ketones• Ethers• Esters• Carboxylic acids• Amines• Amides

• Organic families song-cheesy 3 min http://www.youtube.com/watch?v=mAjrnZ-znkY&feature=related

• Bonding video 3 min http://www.youtube.com/watch?v=oNBzyM6TcK8&feature=related

Diffs Bet Orgs and Inorgs• Elements present

• mpt/freezg pt

• boiling pt

• solublity in HOH

• solubility in organic solvents

• flammability

• bond type

• electrical conductivity

• rxn rate

• side rxns

• product yield

• structure

• ions/molecules in solution

Isomerism

• Fun with Tinker Toys• Draw C2H6O• names & properties• Def: Isomers• The existence of isomers is one reason for

the large # of organic compds• What was the other reason? Be able to list

both.

Draw these molecules one way

• C3H6O C5H12 C3H3Br3O

• C2H2 CH3PO C3H6O2

• C3H4 C2H6O C4H7N2

• C4H4 C3H2O4 C2H5NO

• C3Cl4 C3H5O2 C2H4O2

• C3H4O5 C3H6O3

• C13H10O5N2Cl2

The end