I'm following a procedure on orgsyn.org.

I first weighed out 126.5g of commercial-grade oxalic acid dihydrate. I put this into a toaster oven and baked it at 220°F for 1 hour and 45 minutes. After this baking process, the weight dropped to 91.0g, which I rounded down to the roughly-equimolar 90.0g, mainly to align with my esterification synthesis. The oxalic acid had caked together, which seemed to indicate there was a loss of water, nonetheless.

In this, I poured everything into a 500mL flask. I then added 100mL of anhydrous methanol (dried over molecular sieves) and a stir bar. I then measured out 36.0mL of 93% sulfuric acid and added it slowly via a Ziplock bag. This was added very slowly in the beginning (drip-rate about 1 every 3 seconds) to rapid towards the end (constant slow stream); the color changed very little, but all of the oxalic acid dissolved, which seems to indicate the drip rate is more important when the oxalic acid isn't dissolved. 

After everything was added, I let it heat up. Once it was near-boiling, there was nothing aside from trace cloudiness left in the flask, so I decided to just take it off heat and let it cool instead of filtering first (the procedure opted to filter first).. Once cool, there was a copious amount of crystallization. I let this sit for about 36 hours.

Afterwards, I filtered everything, and let it sit for another 36 hours in the funnel. I tipped everything onto some paper towels and pressed this until I couldn't get any more liquid through. Afterwards, I added the crystals to to 100mL of methanol. I heated this and stirred until near-boiling. I filtered through a small amount of cotton to remove the debris and cloudiness (which worked very well), then let the filtrate cool. 

It produced a copious amount of crystals after a couple hours, but I let it sit for several more. I then filtered off the crystals through a coffee filter. I dried this with several paper towels, then over a fan for a few hours. Afterwards, I got 56.6g of some very thin and nearly-dry crystals. The melting point of this was 54–55.5°C, and it melted quite rapidly. This is within error of the nominal melting point (53–55°C) to prove this is dimethyl oxalate and not, for instance, oxalic acid dihydrate. I blame the slight deviation on my setup, which is improvised, and not professional. 

I decided to improve yield by cooling both the reaction filtrate and the recrystallization filtrate, the former of which also had to be recrystallized. This gave an additional 6.0g. However, the melting point of this was 104–106°C, which is more consistent with oxalic acid dihydrate. So, I did not include it in the final product. 

Thus, the end percent yield is about 48%. The procedure got a yield of 68–76%, so mine is quite a bit lower. I think the main loss was due to the initial drying, which may have not removed as much water as the procedure did, and so, the esterification didn't go to completion. Also, it's possible the recrystallization solvent had water in it, since I used the methanol I had on-hand, which was distilled from HEET. 

I'm following a procedure I found in Small-Scale Synthesis of Laboratory Reagents. To start, I weighed out 38.0g of sodium hydroxide. To this, I added about 45mL of distilled water and stirred to dissolve. I let this cool ambiently. In another container, I mixed together 27.0g of urea, 0.8g of unflavored gelatin, and 23mL of distilled water. This was very endothermic, so I had to microwave it for 30 seconds to get it to dissolve. I let this cool ambiently as well.

In separate contaners, I measured out 94mL of 31% HCl. I then measured out 25mL of distilled water and added 27mL of 87% sulfuric acid to it.

Once everything had cooled, I added 279mL of 10.0% sodium hypochlorite to the sodium hydroxide solution. I then poured the urea solution into a 500mL flask. I placed this in an ice bath and stirred until it was below 10°C. I then put the bleach solution into a ziplock bag, and put the bag in a funnel. I cut a small hole in the bag and let it drip at a moderate speed into the urea solution. There was a slight amount of foaming, but nothing crazy. This was added at a rate that kept the temperature at 11°C, which is about 5–6 drops per second. It took the better part of an hour to add everything.

Once everything was mixed, I immediately removed it from the ice bath and heated it until it hit 72°C. During this time, the color changed from a light yellow to a yellow, and effervescence occurred. Once it hit 72°C, I immediately placed it back into the ice bath to cool. 

Once below 10°C, I added the HCl solution via ziplock bag like before. The drip rate was about 1 drop per second. There was a small amount of foaming and a smoke of hydrazine hydrochloride formed. The temperature was kept at around 15°C (the procedure called for below 10°C, but I couldn't maintain it at this temperature). The addition took about 30 minutes, and the color changed from a yellow to colorless.

I then moved the solution to a glass bottle and added the sulfuric acid solution via ziplock, maintaining the rate at a drop per second, which took about 20 minutes. During this time, extensive effervescence occurred, and the temperature was un-monitored. After everything was added, there was a crystalline precipitate that had formed. I then capped the bottle and placed it into a freezer.

Once it was fully chilled, I filtered everything through a coffee filter. I tested to see if additional sulfuric acid would precipitate anything more, and although a seemingly-vigorous reaction occurred, there was no additional precipitate, so I believe the precipitation was complete. I then dried the filter cake over paper towels and squeezed to remove as much solution as possible. I re-suspended the it in 50mL of cold 91% isopropanol, and then filtered off the isopropanol. I washed everything with 50mL more isopropanol. I then let it dry for 20 hours on top of a fan. 

The yield was 20.0g of a crystalline white powder, which represents a percent yield of 35.5%. The procedure in Small-Scale Synthesis of Laboratory Reagents got a yield of 62% based on hypochlorite. The biggest issue, I presume, is the fact the reaction is highly dependent on an ideal temperature/time curve. Reducing the time by about 40% halved the yield, which is exactly what I did due to the half-scale of the reaction. In the regard, scaling the reaction almost-certainly isn't linear. So, I was unable to achieve ideal temperature and addition rates, and the yield was detrimentally affected.

I ended up recrystallizing this from distilled water to make it as dry and crystalline as my other hydrazine sulfate, and the yield lowered to 29.2%.

Overall, this reaction seemed to be more well-behaved than the previous hydrazine sulfate synthesis. There was also no overflow that occurred in either of the two possible points (mixing of urea and hypochlorite and neutralization) due to the slow addition via ziplock bags. The more-or-less automated dripping allowed for me to not be exposed to nearly as much aerosolized hydrazine as a manual addition. However, it was much longer reaction, taking nearly 2 hours to complete.

I would likely not follow the procedure again except for the slow neutralization, although I'd use just sulfuric acid. A fast reaction in a big flask prevents losses from a foam-over, and a slow neutralization would mitigate an overflow from carbonate. Using just sulfuric acid would prevent losses using too much water, and recrystallizing it from water anyway means any sodium bisulfate contamination is more or less prevented.

I started with 50 325mg aspirin tablets, which I crushed and added to about 200mL of acetone. I stirred until boiling, then filtered through a coffee filter. I washed everything with about 40mL of acetone, then distilled off the acetone, stopping once a solid crashed out. After it was cooled, I added 10mL of 31% hydrochloric acid, then topped it up to the 250mL mark with water. I let it heat up without a condenser until hot to the touch, then put the condenser on and refluxed for 2 hours. Afterwards, I let it cool.

I then filtered everything off, squeezed the liquid remaining out, and put it in another flask. While damp (mass was 11.6g), I added 126mL of dry isopropanol (NaOH → H2SO4 dried), then 2.5mL of 93% sulfuric acid. I then set up for a reflux and heated for 8 hours straight.

Afterwards, I added 126mL of water and added saturated sodium bicarbonate solution until there was no more effervescence. I then extracted it with about 50mL of heptane, which was pipetted off and evaporated (partially by heat and under a stream of air) until a concentrate was obtained. 

This concentrate smelled similar to a glossy magazine while dilute, and somewhat-spearminty while concentrated. The total was about 1mL, which is very far from what was expected, which was about 8%. I blame this on my damp salicylic acid, imperfect drying techniques for the isopropanol, and use of 93% sulfuric acid. I've read isopropyl esters can be tempermental to synthesize, and I'm just glad I was able to isolate some of it. 

I started with a 1-quart bottle of VP Racing Hobby Fuels, advertising 20% nitromethane, as well as 9% oil, with the rest being methanol. I added 225mL of this to a 250mL flask and setup for a fractional distillation, packing my column with shards of tempered glass supported by a small amount of cotton (I had read nitromethane might react with iron, so I couldn't use steel wool). I insulated the flask (body and neck) and the stillhead with aluminum foil.

The distillation was slower than one would expect, about a drip every 2–3 seconds. The stillhead temperature was between 62°C and 64.5°C, consistent with the methanol/nitromethane azeotrope. After a few hours, I stopped the distillation, as there was only about 75mL remaining in the flask. Once cool, I poured the distillate into a flask, then poured the liquid "concentrate" left in the boiling flask into a separate one. After this, I repeated the process 3 times with the remaining racing fuel (I had to insulate half of the column during the second run to try to increase the distilling rate). 

After this was over, I poured the concentrate back into the boiling flask and distilled about 100mL of azeotrope off of it. I then stopped the distillation and left it overnight.

The next day, I continued to distill off the azeotrope. After an hour or two, the stillhead temperature reached 65°C, and there were some isolated drops in the boiling flask, so I decided the azeotrope was finished coming over. I turned off the heat and let everything cool. Once cool, I switched out the glassware for a simple distillation. The liquid level at this point was close to 150mL, and I obtained about 700mL of azeotrope. 

I turned on the heat and insulated the flask with foil again. Quite a bit came over at about 97°C, then the drip-rate slowed and the temperature slowly dropped. Because of how much was still left in the flask (about 100mL), I thought the nitromethane was just having a hard time coming over. So, I increased the heat slightly, but the temperature never increased. I let it coast with heat until the stillhead temperature hit 60°C, then decided to call it, and turned off the heat.

I measured the mass and volume of the distillate to obtain yield and a rough idea of purity. I got 63.0mL of a clear liquid with a calculated density of 1.135g/mL. So, I feel confident in calling this practically-pure nitromethane. Based on inaccuracies, assuming the only impurity is methanol, and assuming the volume doesn't change when nitromethane and methanol mix, the purity is between 98–99%, which is excellent. The smell of nitromethane is similar to a weird hybrid between diethyl ether, isopropyl nitrite, and methyl ethyl ketone, which I wasn't expecting (my drop of nitroethane I made once smelled like fruit snacks).

I also calculated the density of the methanol/nitromethane azeotrope, which came out to be 0.835g/mL. Assuming the volume does not change upon mixing, this means that it contained 12.3% by mass nitromethane, which was slightly more than the azeotrope. I don't have that many theoretical plates in my 20cm column (over 2, but industrial processes go up to 40 stages), so I'm not surprised, but it means I could recover more in the future.

In summary, I got 63.0mL of practically-pure nitromethane and roughly 700mL of methanol/nitromethane azeotrope. I did get less initial fuel than was advertised (around 850mL instead of 946mL), but the overall gross yield of nitromethane was very close to 20% of the original mass (and the error can easily be chalked up to estimations and mechanical losses).

I'm following a procedure derived from a paper, which I've cited. I first measured out an entire 4oz bottle of medical-grade castor oil—totaling 105.9g—which I poured this into a 250mL Erlenmeyer flask. In following a paper, I then measured out about 15g of methanol and placed this into a small flask. To this, I added 1.09g of potassium hydroxide and swirled the flask to dissolve everything.

I then set-up for heating: I placed the 250mL flask into a waterbath at about 45°C, then let the oil heat up with stirring. After a couple of minutes, I added the methanol solution using a funnel (to prevent any of it from getting onto the joint). I then attached a condenser to the flask (joint wrapped in a bit of Teflon tape). Initially, there were two layers, but after a minute or so, a homogeneous, dark yellow solution had formed. 

I let this stir for a total of 60 minutes, trying to keep the temperature below 50°C using a mixture of temperature control, adding cold water, and adding ice.

After the hour, I took it out of the hot water bath and let it cool for a while. After this time, I added the mixture to a 250mL separatory funnel. I then washed it with 3x30mL of a 1M solution of hydrochloric acid (though, I realized afterwards that the procedure said to use a 1M sodium chloride solution), then a brine solution. The organic phase remained quite cloudy, so I added a bunch of anhydrous magnesium sulfate until it appeared dry. I then decanted off the liquid and filtered everything through a coffee filter overnight. 

The next day, I was left with a yellow filtrate, with an oil-like viscosity and smell similar to castor oil. I got roughly 50mL of product. I can't really calculate the yield because I'm unable to truly ascertain purity, but I lost a decent amount throughout the process, especially the drying step.

Nonetheless, I can measure characteristics of the product. The density was 0.89g/mL, which was inconsistent with the product being castor oil, and in the range of biodiesels. Because of this, I have reason to believe that the product is a biodiesel, and not just unreacted castor oil. The flammability is quite low, only somewhat more flammable than oil itself. Burning it in a spoon, it burned very consistently once it was heated to its flash point, only leaving a slight residue behind.

To start, I measured out about 166mL of 7.5% Great Value bleach. I put this into a 500mL flask with a stirbar with an ice bath. I then weighed 16.0g of sodium hydroxide, which I added in roughly 3 portions, keeping the temperature below 20°C. Between additions, I weighed 11.0g of urea in a beaker, then added about 20mL of distilled water. I microwaved this until hot (about 10 seconds), then added 0.4g of unflavored gelatin. I stirred it around with a spatula until most of the gelatin dissolved, then I let it cool. I also mixed together 45mL of 93% sulfuric acid and 45mL of water. This heated up a lot, so I set it aside to cool.

Once this had cooled to room temperature, I added it to the bleach solution. This caused a jump in temperature to about 25°C, accompanied with a lot of foaming. I turned the stirring down and, once the height of the foam stopped rising—about 30 seconds—I took the flask out of the ice bath and let it stir; I re-used the ice bath to cool the sulfuric acid mixture. After about 10 minutes, I turned on the heat. The color changed from a green-ish, to a yellow, to a slightly-yellow before I turned it off, which was when it hit 65°C. This was to allow the heat to "coast" to about 80°C before cooling back down slowly.

After it had cooled to about 40°C, I put the same ice bath around it, added some snow, and started to add the now-cold sulfuric acid solution. There were three stages to this addition: neutralizing NaOH, neutralizing Na2CO3, and neutralizing the hydrazine. The temperature increased until effervescence, indicating the first stage. During the effervescent stage, which was the neutralization of Na2CO3, some solution spilled into the ice bath. This just represents a loss to my yield, but, based on past experience, this "overflow" step indicates the end of the difficult neutralization (although, when done properly, it just presents itself as extensive effervescence instead of overflow). Afterwards, addition of the sulfuric acid solution yielded no bubbling, and produced a white precipitate, which is the desired hydrazine sulfate. I added the entire rest of the sulfuric acid solution, then let everything cool with stirring.

Once this hit about 25°C, I put it in the freezer, and after it was quite cold, I filtered off the precipitate. Once filtered, I scooped the filtrate into some water and heated until it was around 85°C. Because it all didn't dissolve, I added some more water. Once it clarified at about 75°C, I let the solution cool to near room-temperature, then put it in the fridge for about half a day to fully cool. Afterwards, some nice crystals had formed, and I filtered them through a coffee filter. I dried this further by placing the filter onto a paper towel. I then scooped the crystals off of the filter and into a small amount of 91% isopropanol. I swirled it around for a few seconds, then filtered off the crystals through a new coffee filter. I then let this filter dry on top of a fan.

The final yield was 6.2g of sparkly white crystals, representing a yield of 26.0%. This is lower than usual for this reaction by about 10%. I believe that the low yield is primarily due to using a lower concentration of bleach (normally, I use 10%), as well as using too much water in the recrystallization; the overflow, I believe, although a loss, was not as significant as these two. 

To start, I measured out 150mL of undiluted Prestone Antifreeze, which is mostly ethylene glycol with some impurities like a fluorescent dye, bittering agents, and some amount of water and diethylene glycol. I poured this into a jointed Erlenmeyer flask, then added 15mL of 93% sulfuric acid with stirring; the color changed slightly. I then insulated the flask with foil, set up for a fractional distillation, and started heating. I used the fractional column only to prevent reagents and some high-boiling side-products from coming over. As I collected everything below this point, I didn't bother measuring the head temperature and opted to use a stopper instead.

After about 20 minutes post-heating, some product started to condense in the column. This is a most likely mixture of water and a bit of acetaldehyde, which is a side product formed by acid-catalyzed elimination of ethylene glycol. After an additional 10 minutes, the first drops started to come over. This product is a clear liquid with a smell similar to apple. A few minutes after this, water followed, forming characteristic beads on the column, and had little smell. The 1,4-dioxane started to come over a bit after this with some water, which helped clarify the beads on the column. This was likely more dilute than the azeotrope, as the boiling solution was quite hot and likely boiled out anything that was formed. 

After about 35 minutes post-heating, I insulated half of the Vigreaux column to help these high-ish boiling-point products go through the column. I furthered this insulation, covering all boiling-side glassware with aluminum foil except for a couple inches of column, at about the 60 minute mark. The drip-rate at this point was quite inconsistent: There would be about 6 drops in a second, followed by a slow tapering-off of the drip to about 1 every 3 seconds, then another 6 drops in a second. This cycle was about 15 seconds long, and I attribute it to the collection of water on the stillhead male joint—surface tension prevents it from dripping down to the condenser, and once enough collects, it all gets pulled into the condenser and causes a drip-rate surge.

Over the next 20 minutes, the color changed from a yellow to a golden to a very dark brown, and mild foaming was occurring. Because of this, I turned down the stirring slightly. I also took off all of the insulation on the column. At the 90 minute mark, some foam was moving up the column, so I quickly took off the flask insulation and turned off the heat. The foam died down rather quickly, but the liquid was at around 50mL, which was an unacceptably-high amount. So, I turned up the heat again after a couple of minutes, but not as high as last time. 

This ended up not allowing anything to come over. So, at the 100 minute mark, I insulated the column with foil, but not the flask, hoping it would facilitate vapors to come up the column, but keep liquids in the flask. This happened as expected, the drip-rate even going up to a drop per second at times. The liquid volume decreased until the 150 minute mark, at which point I stopped heating and let everything cool. The distillate was starting to go slightly yellow, and I figured I had gotten the majority of the 1,4-dioxane out. I was left with a slight bit of tar in the boiling flask. Upon disassembly, this had a syrup-y smell. In the receiving flask was 126mL of liquid, which smelled sweet and a bit acrid. The density of this was 1.02g/mL, but this doesn't really mean anything when this impure. I poured this into a clean flask to purify.

To start purifying and isolating the 1,4-dioxane, I added potassium hydroxide with stirring until the solution became translucent, about 5g. This caused an instant yellow color change as acetaldehyde underwent base-catalyzed condensation reactions. The translucent nature of the solution indicates the 1,4-dioxane phase-separating out from the water, which breaks the azeotrope and thus anhydrous 1,4-dioxane could be obtained. I let this stir with very gentle heating for about a half hour, with the top of the flask covered in a watch glass.

Over this time, the turned significantly darker, which is good, as it means more acetaldehyde is polymerizing. After the half hour,  I took it off the heat and let the layers separate and cool to room temperature in a freezer. The lower layer—presumably mainly water—was orange-ish, and the upper layer—presumably mainly 1,4-dioxane—was a deep, dark red color. After this cooled, I used a separatory funnel and drained off the lower layer, keeping the upper layer, amounting to 75mL.

To further remove any acetaldehyde, as well as water, I poured the 1,4-dioxane layer into a clean jointed flask. On top of this, I added an additional 4.0g of potassium hydroxide. I then started stirring, attached a reflux condenser, and turned on the heat. I let this reflux mostly unattended for about 3 hours. Afterwards, I let it cool overnight with the condenser still attached.

The next day, I noticed two layers had formed, so I used a separatory funnel to remove the bottom layer. I put the top layer into a jointed flask, then set up for a simple distillation with temperature control and stirring. The first distillate came over at about 84°C, consistant with the 1,4-dioxane/water azeotrope. After about 10 minutes post-boiling, the temperature started to rise slowly, which indicated that the boiling solution only contained a small amount of water.  It rose until 97.5°C, at which point I turned off the heat, as the boiling flask was close to boiling dry.

The distillate was a clear liquid that smelled sweet. I didn't bother measuring yield, as I was going to dry it anyway. I poured the distillate into a jar, along with quite a few molecular sieves. I let this sit for a couple weeks to remove the small amount of water. After this time, I filtered off the sieves through some cotton, then measured its mass and volume. 

In the end, I got 10mL of a clear liquid with a density of 1.024g/mL. This is within the margin of error for anhydrous 1,4-dioxane, as the density decreases from 1.035g/mL from azeotropic 1,4-dioxane with decreasing water content. Also, the amount of sieves I used was overkill, over 50% by volume. This represents a yield of 8.7%, which is honestly terrible. I think the biggest impact was using so many sieves, as I put in over triple the volume prior.

Before the actual synthesis, I needed to make lead (ii) chloride, which I did without measuring out reagents. I added some metallic lead, sourced from cheap fishing sinkers, to some hot dilute nitric acid. Once most of the lead dissolved, I filtered the solution and added it to a sodium chloride solution; a white precipitate immediately formed. I cooled the solution and then filtered off the lead (ii) chloride, washed with some cold water, and dried it. Couldn't calculate a yield, but I assume it was pretty high. 

Now, for the actual synthesis, I scaled-down the procedure written in Brauer's Handbook of Preparative Inorganic Chemistry. I added 3.0g of the dry lead (ii) chloride to 60mL of 31% hydrochloric acid. Brauer makes a mention of ensuring the lead (ii) chloride is a fine powder by grinding it up multiple times, but the way I prepared the lead (ii) chloride formed it as a fine powder, so I disregarded this. This didn't result in a reaction, and the solution was just a suspension of lead (ii) chloride. I put this in an ice bath to cool.

I then set up a chlorine generator and, with strong stirring, I bubbled the chlorine through the lead (ii) chloride suspension. Brauer says it took hours, but it took a few minutes (this may be due to the scaling, though). The lead (ii) chloride dissolved and the solution turned yellow from the formation of hexachloroplumbic acid. I continued generating chlorine for a little bit after the solution cleared to ensure it all reacted.

After this, I made a solution of 1.2g of ammonium chloride and 12mL of water; I added this to the solution, and bright yellow crystals precipitated immediately. I let it sit for about an hour in the ice bath, and then filtered the crystals off. I added some ammonium chloride solution to the filtrate, and nothing else precipitated, so I focused on the filter cake. I washed it with a small amount of anhydrous isopropyl alcohol, then let it dry over a fan. Because it was still slightly damp with hydrochloric acid, I let it dry further overnight in a homemade desiccator, which was a glass jar with some calcium chloride.

The next day, I took the filter paper out and weighed the product. It came out to 2.7g of small, dry, bright-yellow crystals. Brauer got 3.5g, but I figured my yield would be lower. The percent yield was around a 55% from theoretical, which isn't terrible. This product smells of chlorine, which I both assume is because my washing was subpar and the product off-gasses chlorine from the product hydrolyzing in air (though, this doesn't seem to be that significant with this salt compared to the potassium one). I don't have any plans for this compound, and I just wanted to make an interesting coordination complex with reagents that I had on-hand.

I started by crushing up 9 250mg pills of thiamine mononitrate. Without extraction, I added this to a mixture of 20mL of methanol and 8mL of water at room temperature with stirring. In a separate flask, I mixed 0.5g of sodium hydroxide with 5mL of water.  I added this to the thiamine solution dropwise, and it turned a bright yellow, which is from the thiamine freebase. I then added 7mL of benzaldehyde that I had made from benzyl alcohol, dilute nitric acid, and sodium nitrite. The benzaldehyde I had was orange, but that's just from slight impurities. I added a condenser to the top and started heating. 

I heated off-and-on with stirring for 80 minutes. I made sure the flask was hot to the touch, but not refluxing. The top of the reflux condenser smelled sulfurous, but upon taking it off, it smelled like a mix of thiamine (rubbery and gross) and benzaldehyde (cherry). While it was still hot, I filtered off the pill fillers through one coffee filter. I washed the flask and filter with some hot methanol/water in a 5:2 ratio like I had used previously. Some precipitate had crashed out already, so I shook it up and then let this cool in a freezer. 

Afterwards, I filtered off the precipitate and washed with cold water. I then dried it somewhat with a paper towel and scooped it into a flask. On top of this, I added 10mL of the 5:2 methanol to water ratio as before. I let this get to boiling, then kept adding more until everything dissolved. This came out to around 20mL total. I then let it cool to room temperature, then in the freezer. Eventually, some crystal "blobs" had formed. I swirled it, let it cool further, then filtered. I washed this with some methanol/water mixture, then let it dry in front of a fan. I was left with an tan powder that smelled similar to benzaldehyde, but with a more benzoic acid-like smell. However, some thiamine still remained, I believe, and it made objects smell gross when  they came in contact with the benzoin (most notably my fingers).

The total mass was only 1.2g, which represents an 18% yield. I think that the yield is poor because I didn't perfectly control pH or temperature, which the reaction seems to be sensitive to. I think that using thiamine instead of cyanide also hinders the reaction and contributes to the temperature and pH sensitivity, but I can't buy pure cyanide without raising some eyebrows. Also, the benzaldehyde was certainly not 100% pure, so this probably affected the yield as well, but I'm unsure by how much.

My plans for this benzoin is to oxidize it to benzil.

To start this synthesis, I added 10g of 2,5-dichloronitrobenzene to a 250mL flask. On top of this, I added 40mL of 31% HCl and 70mL of water. With stirring, I proceeded to add small amount of 0000 steel wool. I heated off-and-on to keep the solution hot, and the 2,5-dichloronitrobenzene eventually melted. In the middle of the reaction, a precipitate crashed out. So, I added enough water to hit the 200mL mark, and this precipitate redissolved. I eventually added an entire wad of steel wool, and at that point I stopped the reduction. The solution was an orange-ish color, with a black oil at the bottom, which I believe to be unreacted starting material.

Upon cooling, the precipitate crashed out again, so I added an additional 10mL of 31% HCl and topped the water up to the 250mL mark. I re-heated, then hot-filtered the solution into a 250mL 24/40 flask. I was left with a slightly-cloudy orange solution with a black-ish yellow solid caught in the filter. I weighed this, and it came out to 4.6g of unreacted starting material. 

Next came the steam distillation. I added sodium hydroxide slowly until there was a significant color change. This took a while, as the neutralization and dissolution was incredibly exothermic. Eventually, I was left with a solution gray from the precipitate. I set up for a steam distillation outside, and started the distillation. This proved to be incredibly tedious, as the steam-distilled product solidified in the condenser and vacuum takeoff adapter, and I had to keep turning off and on my water recirculator. After the boiling flask bubbled over and contaminated the receiving flask with iron hydroxides and impurities, I gave up on the steam distillation. My three-way distillation adapter also got stuck because I didn't grease the joint, so I broke it while attempting to free it. I ended up having to slowly chip away at the remaining piece that was stuck in the flask's neck. Luckily, the flask was unharmed.

I opted instead for an acid-base extraction, using my thiophene-free toluene. I first filtered off any precipitate using a coffee filter, using the same filter for both for the receiving flask and distilling flask. I then extracted using around 5x25mL of toluene for the distilling flask, and the toluene turned a yellowish-orange color. I then extracted using 2x25mL of a 10mL to 40mL 31% HCl to water solution. Upon addition,the toluene turned a pinkish-red. I collected both of these, then washed the toluene with water. After this wash, the toluene was a slightly-yellow color. I then added the HCl extraction to a flask and, with stirring, I added sodium hydroxide until the pH was strongly basic. I then let the solution cool and filtered. I then repeated this process for the receiving flask, but used 3x25mL. 

With the precipitate caught by the filter, I soaked the entire coffee filter in around 100mL of toluene and stirred it around for a few minutes. I then decanted the toluene from the paste of iron oxides that remained and into a flask. I then extracted using HCl, but used 31% to start instead of dilute. It formed a large amount of precipitate, which dissolved when I added water. I extracted using dilute HCl, but I started to run out of flask space. So, I added 31% HCl and filtered off the precipitate, repeating until no more precipitate was formed. I then washed the toluene with water and put it in the dilute acid. With these extractions, I basified much like the previous times for the dilute extractions, plus the aqueous layer that passed through the coffee filter from the 31% HCl precipitate (this precipitate did not yield anything upon dissolution and basification). I then filtered like earlier.

All of the toluene afterwards was distilled, dried, re-distilled and recovered with a small loss. The end product was 2.0g of a light brown powder.  Out of a theoretical 8.4g, this represents a 23.7% yield. However, if you only count my percent recovery and omit the mass of the unreacted starting material, the yield goes up to 43.9%. I believe that the reason my synthesis was such a mess was because I tried to do it on too large of a scale for my glassware to handle. Unfortunately, I will need to repeat this synthesis in order to have enough product to move onto the next step.