Carboxylic+Acids

carboxylic acids

media type="file" key="Sophie Becky and Alison Honors Chem.m4a" width="273" height="273"

Awesome job on the script! i hope it will take 5 min to say though.

Ok, this is Alison, and I'm going to write in blue. I'm putting pics of the sources on a flashdrive, but I'm also going to put them on here just in case. Do we need to site pics?


 * Heyy guys. so i added the corboxylic acid and i also reformatted one of the charts because it didnt have the subscripts. so the new chart is right below the other chart. It is somewhat similar so i was kind of confused why it was there but i reformatted it anyway. i agree with alison i think we do have enough info i just think we need to just put it all together now. P.S. in the future if you see pink writing in the wiki it is probably me commenting. let's try to either write in our own colors or put our names next to messages so we dont get confused. - Becky


 * I feel like we have all the info we need, unless we need to go into more detail. What do you guys think? Could someone put a carboxyl group? I can't figure out how to. It's just N-C-OH with =O attached to the C. This would be the recognizable aspect in the compounds (something we need to include).**


 * Heyy guys. I was just thinking it might be easier to just get a bunch of information first and then try to go from there. Maybe get a bunch of cites and then divide them so we aren't all going through the same things. Below I added a few cites that looked helpful at a glance

http://ull.chemistry.uakron.edu/genobc/Chapter_15/ http://www.chemguide.co.uk/organicprops/acids/background.html [|http://chem.pdx.edu/~wamserc/C335W00/16notes.htm] http://www.chem.ucalgary.ca/courses/351/Carey5th/Ch19/ch19-0.html ^^ sources that might be helpful. I will try to go through them but i am just trying to get a base down.
 * [|http://www.cem.msu.edu/~reusch/VirtualText/crbacid1.htm]

Alison B Becky N Sophie B**

You will be making a podcast to give information to your classmates about a particular type of organic compound. Including the following: · Some examples of compounds · Structure of these compounds · Information on how these chemicals can be recognized (from the structure) · Naming the compounds · Where can these compounds be found in nature · Use of these compounds Be sure to include citations! The podcast around January 12. Before then you will need · Pictures · A script · Indicate on the script which pictures will be used and when The podcast will only be 5 – 8 minutes in duration

This is a carboxolic acid:
 * Carboxylic acids are organic compounds that contain the carboxyl functional group, which comes at the end of a carbon-atom chain.**

|| || || || || ||
 * = **Carboxylic acid** ||= **Structual Formula** ||= **Source** ||
 * = methanoic acid ||= [[image:http://www.chemgapedia.de/vsengine/media/vsc/en/ch/12/oc/c_acid/nomenklatur/ameisens_egif.gif]] ||= Ants
 * = butanoic acid ||= [[image:http://www.scientificpsychic.com/fitness/butyricacid.gif]] ||= rancid butter
 * = hexanoic acid ||= [[image:http://upload.wikimedia.org/wikipedia/commons/9/94/Trihydroxy-dioxo-hexanoic-acid.png width="144" height="59"]] ||= milk fats, coconut oil, palm oil
 * = lactic acid ||= [[image:http://www.chem.purdue.edu/gchelp/molecules/lacta.gif width="199" height="130"]] ||= sour milk, blood, and muscle fluid
 * = malic acid ||= [[image:http://tbn3.google.com/images?q=tbn:uVUngwuHCDucaM:http://www.thewinemerchantinc.com/images/MalicAcid.gif width="110" height="61" link="http://images.google.com/imgres?imgurl=http://www.thewinemerchantinc.com/images/MalicAcid.gif&imgrefurl=http://www.winemerchantraleigh.com/articles%3Fid%3Dnsession%26article_id%3D212&usg=__Y8v9VS0XpQQbCTzRsNY4dsvsuKw=&h=136&w=247&sz=7&hl=en&start=9&tbnid=uVUngwuHCDucaM:&tbnh=61&tbnw=110&prev=/images%3Fq%3Dmalic%2Bacid%26gbv%3D2%26hl%3Den%26sa%3DG"]] ||= apples
 * = oxalic acid ||= [[image:http://www.chemgapedia.de/vsengine/media/vsc/en/ch/12/oc/c_acid/nomenklatur/ethandis_egif.gif]] ||= rhubarb


 * **Formula ** || **Common Name **  || **Source **  || **IUPAC Name **  ||
 * CH 3 CO 2 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">H || <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">acetic acid  || <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">vinegar (L. acetum)  [[image:http://dontdatethatdude.files.wordpress.com/2008/04/vinegar.jpg]] || <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">ethanoic acid  ||
 * <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">CH <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">3 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">(CH <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">2 <span style="font-size: 12pt; color: black; font-family: 'Arial','sans-serif';">) <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">CO <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">2 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">H || <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">propionic acid  || <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">milk (Gk. protus prion)  [[image:http://www.foodmag.com.au/Uploads/PressReleases/food/Images-20080507/milk.jpg]] || <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">propanoic acid  ||
 * <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">CH <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">3 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">(CH <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">2 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">) <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">3 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">CO <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">2 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">H || <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">valeric acid  || <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">valerian root  [[image:http://www.todayshorse.com/Images/valerianRoot.jpg]] || <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">pentanoic acid  ||
 * <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">CH <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">3 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">(CH <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">2 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">) <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">4 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">CO <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">2 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">H || <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">caproic acid  || <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">goats (L. caper)  [[image:http://www.incubaker.com/tank/wp-content/uploads/2007/08/goat_1.jpg width="877" height="658"]] || <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">hexanoic acid  ||
 * <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">CH <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">3 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">(CH <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">2 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">) <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">5 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">CO <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">2 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">H || <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">enanthic acid  || <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">vines (Gk. oenanthe)  [[image:http://www.gertens.com/sites/default/files/images/Climbing%20vine.jpg]] || <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">heptanoic acid  ||
 * <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">CH <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">3 <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">( <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">CH <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">2 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">) <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">6 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">CO <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">2 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">H || <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">caprylic acid  || <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">goats (L. caper)  [[image:http://www.windrifthill.com/Images/Farm/goat3a.jpg]] || <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">octanoic acid  ||
 * <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">CH <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">3 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">(CH <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">2 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">) <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">7 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">CO <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">2 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">H || <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">pelargonic acid  || <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">pelargonium (an herb)  [[image:http://www.hageprat.com/images/pelly/pelargonium-eden-temperate-royal-oak.jpg]] || <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">nonanoic acid  ||
 * <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">CH <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">3 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">(CH <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">2 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">) <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">8 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">CO <span style="font-size: 12pt; font-family: 'Arial','sans-serif';">2 <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">H || <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">capric acid  || <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">goats (L. caper)  [[image:http://z.about.com/d/esl/1/0/1/a/goat.jpg]] || <span style="font-size: 10pt; color: black; font-family: 'Arial','sans-serif';">decanoic acid  ||

<span style="background-color: rgb(255, 223, 0);"><span style="background-color: rgb(255, 253, 245);">Carboxylic Acid Nomenclature: Properties:
 * Take the name of the parent compound. Then, find the longest continuous chain //that conatins the carboxyl group.// With only one carboxyl group, the last -//e// in the name of the corresponding alkane is replaced with //-oic// acid. With more than one carboxyl group, the full name of the corresponding alkane plus the suffix modified to indicate the number of carboxyl groups is used. For example, //-dioic acid// is for two carboyl groups, //-trioic acid// is for 3, and so on.**
 * React to lose a hydrogen ion
 * Negatively charged ions in water
 * Weaker than most inorganic acids

Uses:
 * Ethanoic and citric acids are used in foods to give them a tart or acidic flavor
 * Bensoic, propanoic, and sorbic acids are used as preservatives and kill microorganisms that cause food to spoil
 * Methanoic and ethanoic acids are the starting material for many chemical processes (ethanoic acid is used to produce polyvinyl acetate -PVA- which is used in latex paint, adhesives, and textile coatings)

__Sources__ Reusch, William. "Carboxylic Acids." __Virtual Textbook of Organic Chemistry.__ 16 July 2007. 1 January 2009. <[|**http://www.cem.msu.edu/~reusch/VirtualText/crbacid1.htm**]>.**
 * Davis, Raymond, H. Clark Metcalfe, John Williams, and Joseph Castka. __Modern Chemistry__. Austin: Holt, Rinehart, and Winston, 2005.

=SCRIPT!!!!!!!!!! YAY!!!!!!!!!!!!!!!!!!!!!!!!!=

Becky: **<span style="color: rgb(255, 0, 220); background-color: rgb(240, 219, 240);">Carboxylic acids are organic compounds that have a carboxyl functional group, which consists of one carbon, two oxygen, and one hydrogen element. The carboxyl group can be found at the end of a carbon-atom chain in a carboxylic acid. This is a carboxylic acid: (show picture). You can see on the carboxyl group from the center to the right. ** Alison: <span style="background-color: rgb(108, 198, 254);">**The way to name carboxylic acids is sort of confusing. If this makes any sense you take the name of the compound. Then you find the longest chain that has the carboxyl group is attached to. If there is only one carboxyl group, the last -e in it becomes -oic acid. If there is more than one carboxyl group you put the name of the compound and then add the suffix in front of -oic, such as -tetraoic to tell how many carboxyl groups there are.**

Sophie: **<span style="background-color: rgb(124, 255, 117);">Carboxylic acids react and lost a hydrogen ion through the process. In water, they are presented as negatively charged ions. Compared to most inorganic acids, their bonds are weaker. **

Sophie: **<span style="background-color: rgb(154, 254, 161);">Carboxylic acids are used in our daily lives. Ethanoic and citric acids are examples of carboxylic acids. They give certain foods a tart or acidic flavor. Bensoic, propanioc, and arobic acids are also examples, and they prevent food from spoiling by killing microorganisms. Methanioc and ethanoic acids are the foundations of many chemical processes, such as the ones that create latex paint. **

Becky**: <span style="color: rgb(255, 26, 219);"><span style="color: rgb(255, 102, 240);"><span style="color: rgb(188, 1, 129); background-color: rgb(255, 255, 255);"><span style="background-color: rgb(254, 134, 244);"><span style="color: rgb(0, 0, 0);">Some examples of carboxylic acids are :

<span style="font-family: Arial,Helvetica,sans-serif;"> <span style="font-family: Arial,Helvetica,sans-serif;"> **Becky**: Ø <span style="font-family: 'Times New Roman'; font-style: normal; font-variant: normal; font-weight: normal; font-size: 7pt; line-height: normal; font-size-adjust: none; font-stretch: normal;"> <span style="background-color: rgb(255, 163, 242);">  <span style="font-size: 12pt; font-family: 'Times New Roman','serif';"><span style="background-color: rgb(255, 163, 242);">Methanoic acids also called formic acids. These acids are the least complex of the carboxylic acids and can be found in bee and ant stings

<span style="background-color: rgb(255, 163, 242);"><span style="background-color: rgb(255, 255, 255);"> <span style="font-family: Arial,Helvetica,sans-serif;">   **Alison: ** Ø <span style="font-family: 'Times New Roman'; font-style: normal; font-variant: normal; font-weight: normal; font-size: 7pt; line-height: normal; font-size-adjust: none; font-stretch: normal;"> <span style="font-size: 12pt; font-family: 'Times New Roman',Times,serif; background-color: rgb(128, 208, 254);">Butanoic acids also called butyric acids. These are fatty acids that give off terrible smells. Butanoic acids are present in rancid butter and parmesan cheese. <span style="font-size: 12pt; font-family: 'Times New Roman','serif';"> <span style="font-family: Arial,Helvetica,sans-serif;"> **

Sophie**: Ø <span style="font-family: 'Times New Roman'; font-style: normal; font-variant: normal; font-weight: normal; font-size: 7pt; line-height: normal; font-size-adjust: none; font-stretch: normal;"><span style="background-color: rgb(119, 254, 147);"> <span style="font-size: 12pt; font-family: 'Times New Roman','serif';"><span style="background-color: rgb(119, 254, 147);">Hexanoic acids, also known as caproic acids, are also fatty acids. These smell even worse than butanoic acids and exist in some animal fats and oils. <span style="font-family: Arial,Helvetica,sans-serif;">  **

Becky**:Ø<span style="font-family: 'Times New Roman'; font-style: normal; font-variant: normal; font-weight: normal; font-size: 7pt; line-height: normal; font-size-adjust: none; font-stretch: normal;"> <span style="font-size: 12pt; font-family: 'Times New Roman','serif';"><span style="background-color: rgb(254, 189, 255);">Lactic acids are especially familiar to athletes. These acids create ATP in humans when there isn’t enough oxygen, which causes muscle pains. These can be found in sour milk as well as muscle fluids. <span style="font-size: 12pt; font-family: 'Times New Roman','serif';"> <span style="background-color: rgb(254, 189, 255);"><span style="background-color: rgb(255, 255, 255);"> <span style="font-family: Arial,Helvetica,sans-serif;">     **

Alison:**Ø<span style="font-family: 'Times New Roman'; font-style: normal; font-variant: normal; font-weight: normal; font-size: 7pt; line-height: normal; font-size-adjust: none; font-stretch: normal;"> <span style="font-size: 12pt; font-family: 'Times New Roman',Times,serif; background-color: rgb(169, 219, 255);">Malic acids are ones which cause interesting tastes in certain foods. It takes part in the source of sourness in apples. <span style="font-size: 12pt; font-family: 'Times New Roman','serif';"> <span style="font-family: Arial,Helvetica,sans-serif;">   **

Sophie**Ø<span style="font-family: 'Times New Roman'; font-style: normal; font-variant: normal; font-weight: normal; font-size: 7pt; line-height: normal; font-size-adjust: none; font-stretch: normal;"> <span style="font-size: 12pt; background-color: rgb(97, 255, 129);">Oxalic acids can be toxic or edible. Combined with other compounds, they create salts called oxalates in a human’s body. They are also useful chemicals in bleaches. They are eaten by humans when they eat rhubarb. <span style="font-size: 12pt; font-family: 'Times New Roman','serif';"> <span style="font-family: Arial,Helvetica,sans-serif;">   **

Becky**:Ø<span style="font-family: 'Times New Roman'; font-style: normal; font-variant: normal; font-weight: normal; font-size: 7pt; line-height: normal; font-size-adjust: none; font-stretch: normal;"> <span style="font-size: 12pt; font-family: 'Times New Roman','serif';"><span style="background-color: rgb(255, 164, 235);">Acetic acids are colorless liquids or crystals that smell like vinegar. They are used in strong oxidizers. Vinegar contains acetic acids. <span style="font-size: 12pt; font-family: 'Times New Roman','serif';"> <span style="background-color: rgb(255, 164, 235);"> <span style="background-color: rgb(255, 255, 255);"> <span style="font-family: Arial,Helvetica,sans-serif;">    ** Alison:**Ø<span style="font-family: 'Times New Roman'; font-style: normal; font-variant: normal; font-weight: normal; font-size: 7pt; line-height: normal; font-size-adjust: none; font-stretch: normal;"> <span style="font-size: 12pt; color: rgb(0, 0, 0); background-color: rgb(159, 210, 255);">Propionic acids are fatty acids that are formed from bacterial fermentation. They can be found in sweat, milk products, and perfume. <span style="font-size: 12pt; font-family: 'Times New Roman','serif';"> <span style="font-size: 12pt; font-family: 'Times New Roman','serif';"> <span style="font-family: Arial,Helvetica,sans-serif;">   **

Sophie**Ø<span style="font-family: 'Times New Roman'; font-style: normal; font-variant: normal; font-weight: normal; font-size: 7pt; line-height: normal; font-size-adjust: none; font-stretch: normal;"> <span style="background-color: rgb(154, 254, 180);"> <span style="font-size: 12pt; font-family: 'Times New Roman','serif';"><span style="background-color: rgb(154, 254, 180);">Valeric acids are also fatty acids that are part of a colorless liquid. They can be found in valerian roots and engineering plastics. <span style="font-size: 12pt; font-family: 'Times New Roman','serif';"> <span style="font-family: Arial,Helvetica,sans-serif;">   **

Becky**:Ø<span style="font-family: 'Times New Roman'; font-style: normal; font-variant: normal; font-weight: normal; font-size: 7pt; line-height: normal; font-size-adjust: none; font-stretch: normal;"> <span style="font-size: 12pt; background-color: rgb(254, 159, 245);">Enanthic acids, also called heptanoic acids, are clear oils with a bad smell. These can be found in vines and cigarettes. <span style="font-size: 12pt; font-family: 'Times New Roman','serif';"> <span style="font-family: Arial,Helvetica,sans-serif;">   **

Alison:**Ø<span style="font-family: 'Times New Roman'; font-style: normal; font-variant: normal; font-weight: normal; font-size: 7pt; line-height: normal; font-size-adjust: none; font-stretch: normal;"> <span style="font-size: 12pt; font-family: 'Times New Roman','serif';"><span style="background-color: rgb(134, 207, 254);">Caprylic acids are liquid fatty acids with terrible tastes. They can be found in dyes and perfumes. <span style="font-size: 12pt; font-family: 'Times New Roman','serif';"> <span style="background-color: rgb(134, 207, 254);"> <span style="background-color: rgb(255, 255, 255);"> <span style="font-family: Arial,Helvetica,sans-serif;">    **

Sophie**Ø<span style="font-family: 'Times New Roman'; font-style: normal; font-variant: normal; font-weight: normal; font-size: 7pt; line-height: normal; font-size-adjust: none; font-stretch: normal;"><span style="background-color: rgb(122, 255, 166);"> <span style="font-size: 12pt; font-family: 'Times New Roman','serif';"><span style="background-color: rgb(122, 255, 166);">Pelargonic acids are also fatty acids that appear to be clear to yellowish oily liquids. These can be found in pelargonium, which is an herb. <span style="font-size: 12pt; font-family: 'Times New Roman','serif';"> <span style="font-family: Arial,Helvetica,sans-serif;">   **

Becky**:Ø<span style="font-family: 'Times New Roman'; font-style: normal; font-variant: normal; font-weight: normal; font-size: 7pt; line-height: normal; font-size-adjust: none; font-stretch: normal;"> <span style="font-size: 12pt; font-family: 'Times New Roman','serif';"><span style="background-color: rgb(254, 174, 245);">And finally capric acids, also called decanoic acids, are also fatty acids. They can be found in animal fats and oils and are used to make perfumes and fruit flavors

ALL: We hope you enjoyed learning all about carboxlic acids :) http://www.3dchem.com/molecules.asp?ID=389 http://chemicalland21.com/industrialchem/organic/FORMIC%20ACID.htm http://www.3dchem.com/moremolecules.asp?ID=395&othername=Butanoic-acid http://www.brianmac.co.uk/lactic.htm http://www.bartek.ca/malic_acid.html http://growingtaste.com/oxalicacid.shtml http://www.cdc.gov/niosh/npg/npgd0002.html http://chemicalland21.com/specialtychem/perchem/VALERIC%20ACID.htm http://www.answers.com/topic/heptanoic-acid http://www.answers.com/topic/caprylic-acid http://chemicalland21.com/industrialchem/organic/n-NONANOIC%20ACID.htm http://www.answers.com/topic/capric-acid