Skunk spray

Butene-l-thiol is one component of skunk spray. How would you synthesize this substance from methyl 2-butenoate From 1,3-butadiene ... 

Chemistry of Skunk Spray. Professor William F. Wood, Department of Chemistry, Hum-boldt State Univeristy, http //sorrel.humboldt.edu/ wfw2/chemofskunkspray.html... 

These are volatile compounds and do have rather dreadful smells. They also occur in skunk spray in the form of their acetate esters. These are much less volatile and so contribute less to the immediate odor. However, on contact with water, they are slowly converted to the free thiols, a reaction that accounts for the persistence of skunk odor for days or weeks. The chemical components of skunk defensive secretion vary somewhat from species to species but thiols play a prominent role in all cases. 

Sulfur compounds are used to make rubber strong enough to be used in tires, in a process called vulcanization. Sulfur is also used to make detergent, paper, fertilizers, and medicines. Several sulfur compounds have a strong odor to them. Onions, garlic, skunk spray, and even bad breath get their unique odor from sulfur compounds. Sulfur by itself has no smell. 

Skunks are small animals that wage powerful defensive warfare in the form of spray that has a sickening offensive odor. The compounds that are responsible for skunk spray odor are organosulfur compounds. Although seven or more such compounds have been isolated from the spray of the striped skunk, Mephitis mephitis, it is now believed that there are only three major ones trans-2-butene-l-thiol, t ra .v - 2 - b u t e n y I -1 - thioacetate, and 3-methyl-1-butanethiol5 ... 

Offensive use of thiols. Skunks spray thiols to protect themselves from people, dogs, and other animals. 

Authentic skunk spray has become valuable for use in scent-masking products. Show how you would synthesize the two major components of skunk spray (3-methylbutane- 1-thiol and but-2-ene- 1-thiol) from any of the readily available butenes or from buta-1,3-diene. 

Think Critically The formula for one compound that produces the odor in skunk spray is CH3CH2CH2CH2SH. Draw and examine the structural formula. Does it fit the definition of a substituted hydrocarbon Explain. 

Humans sense of smell, or olfaction (from the Latin, olere, to smell + facere, to make), is highly developed. We can recognize approximately 10,000 scents, including mer-captans (disagreeable-smelling compounds contained in skunk spray), which we can detect at a concentration of one part per billion. 

All three isomers of butyl mercaptan are mobile liquids (liquids that flow easily) with very strong skunk-like odors. At one time, chemists thought that the butyl mercaptans were responsible for the distinctive odor of skunk spray. Research has now shown that some mercaptans are found in skunk spray, but the butyl mercaptans are not among them. 

Wood, William F. Chemistry of Skunk Spray. Humboldt State University. 

Skunks Analysis of skunk spray yields a molecule with 44.77% C, 7.46% H and 47.76% S. What is the chemical formula for this molecule found in the spray from skunks that scientists think is partly responsible for the strong odor ... 

Most liquids and gases that contain sulfur tend to have rather noxious odors. Notable examples include sulfur dioxide (SO ), hydrogen sulfide (FI S), and mercaptans the class of sulfur-based compounds that are responsible for the intense odor of a skunks spray. 

Skunk Mephitis). When threatened, skunks spray an evil-smelling secretion from their anal glands at their enemies. This consists mainly of ( )-2-butene-l-thiol, 3-methyl-1-butanethiol, and other thiols as well as their acetates. These acetates are apparently responsible for the persisting effect of the secretion since they are cleaved by water to the thiols. 

Many hunting dogs enjoy standing nose-to-nose with a skunk while barking furiously, oblivious to the skunk spray... 

The chemicals in skunk spray, all contain sulfur. This may be the world s worst smell. 

Second, almost all of the low-molecular-weight sulfur compounds have objectionable (to humans) odors. Thus, in defense, the skunk sprays offenders with a mixture of thiols (and other compounds) containing the disulfide, (E)-2-buten-l-yl methyl disulfide, and the thiols 1-butane thiol, 3-methylbutane-l-thiol, and ( )-2-butene-l-thiol. Additionally, although the mixture of low-molecular-weight hydrocarbons used as natural gas is essentially odorless (to humans), contamination of that material with only a few parts per billion (ppb) of a mixture of low-molecular-weight (mostly Cs-isomers) thiols is sufficient to allow humans to smell a gas leak. ... 

The foul smell that skunks spray is due to a number of thiols, one of which is methanethiol, CH3SH. A 10.(X)cm sample of methanethiol was exploded with 60.00cm of oxygen. Apply Avogadro s law and determine the final volume of the resultant mixture of gases when cooled to room temperature. 

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