Basic Chains

2. Basic Chains HYDROCARBONS…just carbon and hydrogen compounds ALKANES… just single bond C-C, saturated with hydrogenALKENES… double bond C=C, less hydrogen than alkanesALKYNES… TRIPLE BONDED C to C, even fewer hydrogen YOU MUST indicate where the double or triple bond is!

3. Hydrocarbon chains can be branched or straight line chains – even if they “bend” like bottom left. images from: http://www.howe.k12.ok.us/~jimaskew/chem/calkane.htm

4. Butane has 10 hydrogen atoms attached to just 4 carbons. The white balls are the H, the black ones are the C atoms. Alkanes have a general formula of CnH2n+2 image from: http://www.chm.bris.ac.uk/motm/thalidomide/structuraliso.html

5. Butene has one DOUBLE BOND between carbon atoms. It has a general formula of CnH2n

6. BUTYNE has a TRIPLE BOND image from: http://dbhs.wvusd.k12.ca.us/webdocs/Bonding/Lab-ModelBuilding/Lab-ModelBuilding-1.html

7. Halo Carbons Meet difluorochloromethane. A neat halocarbon example. It has 3 halogen groups attached to a small hydrocarbon. Does the name make sense? image from: http://www.airliquide.com/en/business/products/gases/gasdata/index.asp?GasID=14

8. ESTER I found this lady on the internet, her name appears to be Ester. She has NOTHING to do with organic chem, but finding a good “ester” picture is hard to do. Esters have a look like what you see below. The “R’s” stands for a small or large hydrocarbon groups attached to the C and to the O respectively.

9. Alcohols An alcohol group is an –OH group THAT DOES NOT DISSOCIATE when dissolved into water. It is NOT an Arrhenius Base. The –OH group is attached to an “R” group of some sort. This “R” group is a “prop- group” (3 carbons), and the –OH is on the FIRST carbon, so this is 1-propanol. Many organic chemicals we saw in the smell lab had rings like this. The circle means that all the carbons are double bonded together in a sort of shorthand style.

10. Ether Ether Ether A beautiful oxygen bridge between two “R” groups. This one is called di-methyl ether because the oxygen bridges 2 methyl groups.

11. ALDEHYDES Aldehydes have a carbon center double bonded to an oxygen plus a hydrogen. The carbon is then attached to an “R” structure (a ring hydrocarbon with an NO2 group) Nice aldehyde, eh?

12. Ketone A ketone can sort of look like an aldehyde, but there is NO hydrogen attached to the carbon atom. The devil is in the details. That expression means that nearly all these organic compounds look exactly alike and you ALWAYS need your table R to figure them out. Don’t be lazy, do not guess, look them up.

13. 13

14. ORGANIC ACIDS All organic acids have that COOH group, and it’s usually on one end or the other. This picture shows the –OH group with a bond between the “O” and the “H”, which is good chemistry, but we usually shorten it to just –OH.We “know” the bond is really there without seeing it.

15. AMINES "R" US Amines have a SINGLE NITROGEN atom with three bonds to three different “R” groups. Just like that “N” in the middle of this giant organic molecule. image from: http://www.acdlabs.com/iupac/nomenclature/79/r79_548.htm

16. image from: http://www.hcc.mnscu.edu/programs/dept/chem/V.18/page_id_34713.html

17. Naming Hydrocarbon Chains NAME THIS HYDROCARBON click ahead for the answer… image from: http://kjd.edu-ctr.pref.kanagawa.jp/edb2/chem/models/3d/1_2-Dimethyl-butane.jpg

18. The long chain is four carbons long, so it’s a type of BUTANE. There are 2 methyl groups attached at carbons number 2 and 3. It’s called 2,3-dimethyl butane. Count the hydrogen atoms. How many does it have?

19. Organic Reactions There are several reactions in organic chem that we need to review and get to recognize. They are: substitution: one atom or group is replaced by another addition: atoms are added where a double or triple bond exists, the bond gets smaller and atoms are added into the molecule fermentation: oxidation without oxygen (produces alcohol) esterification: acid + alcohol  ester + water hydrolysis: ester + water  acid + alcohol saponification: fat + NaOH  glycerol + soap oxidation: the combustion of hydrocarbons

20. Substitution Reactions CH4 + Cl2 HCl + CH3Cl (chlormethane) CH3Cl + Cl2  HCl + CH2Cl2 (dichloromethane) CH2Cl2 + Cl2  HCl + CHCl3 (trichloromethane) CHCl3 + Cl2  HCl + CCl4 (tetrachloromethane) In each step, one hydrogen atom is replaced with a chlorine atom, the extra chlorine combines with the H to form hydrogen chloride (HCl)

21. Addition Reactions + Br2  In addition reactions, a double bond breaks into a single bond and two atoms can be added. Sometimes a triple bond can break into a double and two atoms can be added as well.

22. FERMENTATION This is an organic process that requires YEAST organisms. They undergo oxidation in the absence of oxygen (anaerobic). The products are carbon dioxide and ethanol. With the proper conditions, those products are champagne. CO2 yeast enzymes  + sugar in yeast yields ethanol & carbon dioxide

23. Esterification vs. Hydrolysis ORGANIC ACID + ALCOHOL ESTER + WATER ESTERIFICATION reaction goes while  HYDROLYSIS GOES to the left THESE ARE OPPOSITE REACTIONS the H+ ion represents the acid catalyst image from: http://www.crnasomeday.com/Images/chem/esterification.gif

24. Esterification This means making an ESTER. An alcohol and an organic acid combine to make an ester and water. HYDROLYSIS This reaction takes an ESTER and water, break the water and combine the products into alcohol and an organic acid. The reverse of esterification.

25. SAPONIFICATION ESTER + 3NaOH  glycerol + 3-soap Look for the ester groups, the 3 base3, the triple alcohol group (glycerol), and all the functional groups. Get relaxed looking at this and appreciate how much you have learned already about organic chemistry. THIS is hard stuff. image from: http://www.chem.latech.edu/~deddy/chem122m/L06U00Soap122.htm

26. oxidation, organic chem style

27. OXIDATION of HYDROCARBONSwith sufficient oxygen present CH4 + 2O2 2CO2 + 2H2O without sufficient oxygen present 2CH4 + 3O2 2CO + 4H2Othe CO = CARBON MONOXIDE CH4 + O2 C + 2H2O the loose carbon = SOOT

28. Reference Tables Practice using your reference tables. Use the homework answers and your returned Organic Chem Smell Lab to practice drawing and interpreting organic molecules. LOOK INSIDE YOUR TEXTBOOK AS WELL! It might help! See the happy students reading their chemistry textbook and finding bliss and many answers to life’s many questions. Chemistry is part of your life. Life is a great breakfast cereal. You may read your text over breakfast everyday, no problem!

29. Although you don’t like to hear it, maybe reading this will impact you in a positive way. In a few weeks you will take the Chemistry Regents Exam. It will be hot and you will be in the gym with hundreds of other misfortunate souls who would all rather be playing in the sun, having fun, being normal. No one will actually be happy in the gym that day, not really. The only way to make your time there even remotely reasonable is to be prepared for this long, tedious, cumulative test. One way to do that is to buy a review book NOW. The sooner you start the easier it will be. This may be the hardest test of your life. Many lessons can be learned from a failure of a test like this. That is a lesson that you will learn if you fail. You don’t want to learn that lesson. Get a book. Start studying soon. Now. Stop fooling yourself that you have time. Time waits for no man or woman. The time is now. There is no time like the present. No time outs left. Just Do It! It is NOT COOL to fail. Rise up to this challenge and meet it. Do your best with the time you have now, plan to come to the evening session. Come in during lunch. Take advantage of all your opportunities to celebrate your knowledge rather than waste your time with not trying as hard as you can.