dimethylsulfoxide

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 Diazepam (valium) C16H13ClN2O

  • Appearance: White solid
  • Molar Mass: 284.74 g/mol
  • Density: 1.08 g/cm3 (at 20°, solid)
  • Melting Point: 125-126°C
  • Boiling Point: n/a 
  • pKa: n/a

Diazepam is a benzodiazepine and well-known sedative used to combat all sorts of conditions like anxiety, depression, seizures, and even restless leg syndrome. While having a wide range of uses, it also comes with some bad paradoxical effects like actually worsening seizures. It is most well known for subduing anxiety attacks since diazepam rapidly sets in. It should be noted that it is highly advised not to overuse diazepam due to easy dependency formation. 

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Acetylcholine (ACh) C7H16NO2Cl

(data from the chloride salt of acetylcholine chloride)

  • Appearance: White/off-white powder
  • Molar Mass: 181.66 g/mol
  • Density: n/a
  • Melting Point: 146 - 150°C
  • Boiling Point: n/a
  • pKa: n/a

First identified in 1915 by Henry Dale, Acetylcholine is a neurotransmitter and was in fact the first one to be identified. It has uses in both the Central nervous system and the Peripheral nervous system as a modulator. In the CNS, it is known to have inhibitory functions where as in the PNS it actually activates muscles by opening ligand-gated sodium channels. In the CNS, it has a variety of effects on arousal and reward when acting as a neuromodulator. IT has an interesting structure as a polyatomic compound with an ammonium in between four carbons. AChCl is commercially available. 

2

Adamantane C10H16

  • Appearance: White/off-white powder
  • Molar Mass: 136.23 g/mol
  • Density: 1.08 g/cm3 (at 20°, solid)
  • Melting Point: 270°C
  • Boiling Point: sublimes 
  • pKa: n/a

Adamantane is a crystalline compound and is the simplest diamondoid. It consists of four cyclohexane rings in the “armchair”. The arrangement of atoms in adamatane is the same as a diamond crystal. Adamantane is unique in that it is rigid and almost free of strain and stress. It was first synthesized from Meerwein’s ester, however this process resulted in very low yield. Adamantane cations can be produced and are highly stable, and this is due to a three-dimensional aromaticity (homoaromaticity). Since it is an unfunctionalized hydrocarbon, it’s uses are limited, however aminoadamantanes have come up in medicine as an antiviral for influenza (though this has been discontinued) and as an antiparkinsonian drug. 

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Acetaldehyde C2H4O

  • Appearance: Colorless liquid
  • Molar Mass: 44.05 g/mol
  • Density: 0.784 g/cm(at 20°C)
  • Melting Point: -123.37°C
  • Boiling Point: 20.2°C 
  • pKa: 13.57

Acetaldehyde is one of the most important aldehydes, occuring in coffee and bread. It’s more well known as being the metabolite of ethanol by alcohol dehydrogenase, thought to be the main cause of hangovers. It undergoes keto-enol tautomerism, but only a small fraction of acetaldehyde is in the enol tautomer. Acetaldehyde used to be a precursor to acetic acid, however now it’s more important as a precursor to pyridine derivatives like pentaerthritol. It’s toxic when applied for extended periods, is an irritant on the skin, eyes, and mucous membranes, and is a possible carcinogen. It’s found smoke from cannabis and tobacco.

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(−)-trans9-tetrahydrocannabinol (THC) C21H30O2

  • Appearance: clear solid crystal (cold), waxy, viscous (warm)
  • Molar Mass: 314.469 g/mol
  • Density: n/a
  • Melting Point: n/a
  • Boiling Point: 250°C
  • pKa: n/a
  • (literally could not find ANY data for this)

Tetrahydrocannabinol is the main psychoactive component of cannabis. It has some analgesic effects and is known to increase appetite and enjoyment of food. It’s most famous for it’s effects on cognitive functions, leading to the substance being banned in many areas. These effects can actually be lessened by opioid receptor antagonists like naloxone. While being an illegal substance, the medical properties of THC have been investigated and seems to have many beneficial properties for those undergoing chemotherapy, people suffering from AIDS, multiple sclerosis, and neurological disorders like Tourette syndrome. The main metabolite of THC is 11-hydroxy-Δ9-tetrahydrocannabinol (11-OH-THC), where the methyl group gains a hydroxy group. 

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1,4-dioxane C4H8O2

  • Appearance: clear liquid
  • Molar Mass: 88.11 g/mol
  • Density: 1.033 g/cm3
  • Melting Point: 11.8°C
  • Boiling Point: 101.1°C
  • pKa: -2.92

1,4-dixoane is a heterocyclic structure that shares a similar chair conformation with cyclohexane. Due to the C-O-C bonds, it’s classified as a ether. The main use of 1,4-dioxane is as a stabilizer for 1,1,1-triochloroethane while in an aluminum container. It’s a good aprotic solvent that’s hygroscopic. The oxygen centers of the compound are lewis bases. It’s main solvent uses are in dyes, greases, mineral oils, fats, etc.

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Oxymercuration-reduction

When the formation of an alcohol from an alkene is wanted, but the formation of carbocations unwanted, oxymercuration-reduction is the reaction to take. It’s a two step reaction, with the oxymercuration being first, followed by the reduction. In this reaction, the alkene attacks and is attacked by the mercury diacetate, displacing one of the acetates and forming a cyclic mercurinium ion. This reaction also takes place in water with THF as a solvent. The water then attacks the more stable position on the cyclic structure, forming a protonated alcohol with the mercury hanging off. 

Next, the mercury is cleaved with the addition of NaBH4 by a mechanism that is currently unknown. (oops).

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Addition of Bromine to an Alkene in water

In the addition of bromine to an alkene, the pi-bond of the alkene attacks one of the bromine atoms, and the atom attacks the other end of the pi-bond, forming a cyclic bromonium ion after the other. Before the newly formed bromide ion can attack and break the bromonium ion, the water molecules attack at break it open. The protonated alcohol is then deprotonated, forming a halohydrin.

Acid-catalyzed addition of an Alcohol to an Alkene

The acid-catalyzed addition of an alcohol to an alkene undergoes the exact same reaction as the addition of water. The alcohol, in this case, methanol, is added in excess. The methanol protonated by the acid catalyst and then deprotonated by the alkene. This causes it to form a 2° carbocation which the methanol attacks, forming a protonated alkoxide. This is subsequently deprotonated by the excess alcohol.

2

Dopamine C8H11NO2

  • Appearance: Colorless solid
  • Molar Mass: 153.18 g/mol
  • Density: 1.26 g/cm3 (at 20°, solid)
  • Melting Point: 128°C
  • Boiling Point: decomposes 
  • pKa: n/a (an anime, so it’s an organic base). 

Dopamine is a neurotransmitter in humans and animals. It has a major role in reward-motivation. Dopamine is released into the brain in increased levels when “rewards” are completed. Several addictive drugs play on this like cocaine and amphetamine-based drugs. Outside the nervous system and the brain, dopamine does have some uses in the body like an inhibitor to norepinephrine in blood cells and increasing sodium excretion. Dopamine gets it’s name from it’s metabolite precursor, L-DOPA. Dopamine however cannot breach the blood/brain barrier, however it still is useful if it’s needed to be intravenously infected. In the body, it’ broken down by the enzyme monoamine oxidase via oxidation. However it can also be autooxidized by direct oxygen, resulting in quinones and free radicals. One of dopamine’s nicknames is the “pleasure chemical”. 

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Cis/Trans and E/Z Naming

  • Cis - same side
  • Trans - opposite side
  • E - opposite size (think eppesite side)
  • Z - same side (think zame zide)

When you name alkenes, you have to account for the isomer that you’re talking about. Cis/Trans naming is used for alkenes in chains or disubstituted alkenes like the top row of alkenes, 2-butene and 3-hexene. Cis/Trans and E/Z could be applied to these. The cis isomer is when the two hydrogens are on the same side of the double bond and the two alkyl chains are on the other. The trans isomer is when they’re switched. So going across the image above, the structures would be:

  • Trans-2-butene or (E)-2-butene
  • Cis-2-butene or (Z)-2-butene
  • Trans-3-hexene or (E)-3-hexene
  • Cis-3-hexene or (Z)-3-hexene

Once there is more than one substituent on each sp2 carbon, the cis/trans naming cannot be used. E/Z naming is essentially the same thing, however it’s based on the “weight” and “heaviness” of the substituents. The heavier the substituent, the higher it ranks. When judging how to name E/Z, the attachments on each sp2 carbons are identified, never judge across the double bond. Only compare the two substituents connected to the same carbon, as circled in the image above. The heavier one is chosen. In the second row, there is:

  • (E)-2,3-dibromo-2-butene
  • (Z)-2,3-dibromo-2-butene
  • (E)-3,4-dimethyl-3-hexene
  • (Z)-3,4,-dimethyl-3-hexene

Issues arise when the same substituent is connected to the same carbon like the first two structures in the third row. The first structure has two ethyl groups coming off the sp2 carbon and in the second one, there are two hydrogens on the sp2 carbon. This leaves it so that there can’t be isomers of the structure. Underneath, on the last row, is maleic and fumaric acid. These two are isomers of each other and are common examples of E/Z isomers. The last structure is (Z)-4-methyl-1,4-hexadiene. You’ll notice that there are two double bonds in the structure, but only one of them can be an E/Z. Since the terminal double bond has two hydrogens, it’s ineligible to be an isomer. 

(sorry for the long post, I hope this helps!!)

2

Addition of Hydrogen Halides to Alkenes and Alkynes

When a hydrogen halide (bromide or chloride) to an alkene, the double bond attacks the hydrogen, forming a carbocation on the more stable carbon (generally always a 2° or 3°) and a bromide ion. The bromide ion reacts with the newly formed carbocation to form the alkyl halide. it’s a very simple reaction.

The exact same thing occurs when reactings an alkyl halide with an alkyne, however after it’s been reacted, it can have a second hydrogen halide added to it, resulting in a geminal alkyl halide. When the second hydrogen halide is added, it undergoes the same reaction, resulting in the diaddition shown. 

edit: oops fixed the direction of the arrows in the carbocation/bromide part. Thanks to rougelette for pointing it out!!

2

Disulfiram C10H20N2S4

  • Appearance: Beige powder
  • Molar Mass: 296.539 g/mol
  • Density: 1.3 g/cm3
  • Melting Point: 71.5°C
  • Boiling Point: 117°C (at 17 mmHg)
  • pKa: n/a

Disulfiram is a drug that is used to support chronic alcoholism by blocking the enzyme that breaks down acetaldehyde to acetic acid, causing a build up. Acetaldehyde is the metabolite of ethanol after it’s been broken down by alcohol dehydrogenase. The build up of acetaldehyde is what is generally thought to be the cause of a “hangover”. Thus, disulfiram causes a larger build up of acetaldehyde, which leads to a more severe hangover. This effect is what can lead to the breaking of chronic alcoholism.

2

Methylamine CH5N

  • Appearance: Colorless gas
  • Molar Mass: 31.06 g/mol
  • density: 694 kg/m3
  • Melting Point: -93.10 °C
  • Boiling Point: -6.6°C 
  • pKb: 3.36

Methylamine is a derivative of ammonia and is the simplest primary amine. It’s commonly sold as anhydrous gas in metal containers. It’s a relatively easy compound to synthesis in lab, being a simple reaction between methanol and ammonia. Methylamine is a great nucleophile that’s also highly basic with little to no hindrance. Liquid methylamine has solvent properties similar to ammonia. It is toxic and listed as a List 1 Precursor chemical by the DEA since it’s well known for it’s use in the production of methamphetamine. 

2

Toluene C7H8

  • Appearance: Colorless liquid
  • Molar Mass: 92.14 g/mol
  • Density: 0.87 g/cm3
  • Melting Point: -95°C
  • Boiling Point: 111°C
  • pKa: 45

Toluene is a monosubstituted benzene ring (one hydrogen is replaced by a methyl group). It’s aromatic and is a useful organic solvent, having replaced benzene as a less toxic solvent. It’s also very useful for dissolving inorganic chemicals like sulfur, phosphorous, bromine, and iodine. Toluene can be used to induce a mild intoxication though it can cause unconsciousness and death. It has a high octane number and is used as an octane booster in fuels. Toluene is used as a precursor for compounds like toluene diisocyanate and TNT (trinitrotoluene). 

2

Benzene C6H6

  • Appearance: Colorless liquid
  • Molar Mass: 78.11 g/mol
  • Density: 0.8765 g/cm3
  • Melting Point: 5.5°C
  • Boiling Point: 80.1°C
  • pKa: n/a

Benzene is a 6-carbon aromatic ring. It has a continuous pi bond but is often depicted with alternative single-double bonds. It’s highly flammable and is a common part of gasoline, due to it’s high octane number. It’s a precursor to countless other organic compounds and is also used as a solvent. Benzene is carcinogenic so it’s uses have been cut down drastically. Toluene, a methylated benzene, has mostly replaced benzene in the lab since they are so similar and Toluene is less toxic.

2

Formaldehyde CH2O

  • Appearance: Colorless gas
  • Molar Mass: 30.03 g/mol
  • Density: .8153 g/cm(at -20°C)
  • Melting Point:-92°C
  • Boiling Point: -19°C
  • pKa: 13.3

Formaldehyde is the simplest carbonyl. It has a very simple structure but can take on multiple forms, making it difficult to handle. At room temperature, it’s a colorless gas that is an irritant and well known as a human carcinogen. It can form a trimer (1,3,5-trioxane) which can be useful as a way to use anhydrous formaldehyde in lab, not having to deal with gases. It can also form large polymer chains. In water, formaldehyde is hydrogenated and forms methanediol. Formaldehyde is a common precursor compound and also used as a disinfectant for bacteria and fungi. Methanol’s toxicity is primarily caused by formaldehyde. This formaldehyde is caused methanol being broken down to formaldehyde by the enzyme alcohol dehydrogenase, similar to how acetaldehyde (ethanal) is formed when ethanol is metabolized. However formaldehyde is much more toxic than acetaldehyde.