musings on music and life

April 24, 2017

Professional Courtesy

Filed under: Carnatic Music, Uncomfortable truths — sankirnam @ 3:05 pm

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This situation has happened to me way too many times now, and I need to vent here. It’s just a matter of having basic professional courtesy as a musician. If you don’t have the instrument, or are unwilling to pay for transportation costs, then don’t accept the engagement. It’s that simple.

As a professional, I do this myself – before accepting a concert engagement, I always inquire for the sruthi (pitch) of the main artist and make sure I have access to the correct instrument. It’s amazing to me how so many others don’t do this, and instead hope that someone else will lend their instrument for their use. I have actually had some of my mrudangams come back basically destroyed after loaning them out for concerts.

I do not go to all the trouble of maintaining my instruments just so that others can use them in concerts. This would not be such a big deal if I were living in India (or Chennai specifically), where access to mrudangam artisans and repairers is easy. The mrudangam is an incredibly finicky, high-maintenance instrument, and I don’t put a lot of my own time, effort, and money into maintaining my instruments just so that other people can use them.

The same thing can hold for concert organizers, if they read this: don’t expect one musician to give his/her instrument (especially a high-maintenance instrument like the mrudangam in the US) to another musician.

</end rant>

April 9, 2017

Classics in Organic Chemistry, Part X

Filed under: Classics in Organic Chemistry — sankirnam @ 8:14 pm

It’s been over a month since Prof. Olah passed away, and I haven’t made a post here since then, so this one can also be dedicated to some of the work that he did.

Prof. Olah may have been best known for carbocation and superacid chemistry, but his research covered a very broad swath of organic chemistry, including novel synthetic methods, nitration, Friedel-Crafts chemistry, onium ion chemistry, fluorine chemistry, polymer chemistry (carbocationic polymerization), and physical organic chemistry. This post will be about work that I did during my PhD (2008-2014), and was in full force during the time Prof. Olah received the Nobel Prize (1994).

This topic is called superelectrophilic activation and can be thought of as a way to rationally design new electrophiles for Friedel-Crafts chemistry, as well as develop new types of Friedel-Crafts reactions. But first, some background is required.

In the 1970’s, Prof. Olah’s group (then at Case Western Reserve University, Cleveland), as well as Brouwer and Kiffen at Shell Amsterdam, had noted that acetylium salts could carry out hydride abstraction from tertiary alkanes. Prof. Olah noted the solvent dependence of this reaction – it took place in superacid media (e.g. HF-BF3 or FSO3H), but not in aprotic solvents. A similar phenomenon was observed with the nitronium ion (NO2+ salts); in superacid solution, the nitronium ion was capable of reacting with methane, forming nitromethane (although the yields are low and this is not preparatively useful, it is in stark contrast to the usual scenario of no reaction).

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Slides are from my PhD Defense, University of Southern California, 2014.

Around the same time, Prof. Koichi Shudo (University of Tokyo), was doing independent but related research in a similar area. Prof. Shudo had just come back to Japan after doing a postdoc with Prof. Paul G. Gassman (University of Minnesota). Gassman’s influence is evident in Prof. Shudo’s research in Physical Organic Chemistry, as he was doing research at the time on nitrenium ion chemistry. Prof. Shudo was a brilliant chemist and bought a lot of rigor to his investigations on superelectrophiles. I never met him, but I did meet his junior colleague, Prof. Tomohiko Ohwada, at Prof. Olah’s 85th birthday at USC a few years ago.

In any case, Prof. Shudo and his colleagues observed that when N-phenylhydroxylamine or nitrosobenzene was mixed with benzene and TFA (trifluoroacetic acid), N-arylation was observed, yielding diphenylamines. On the other hand, when TFSA (triflic or trifluoromethanesulfonic acid) was substituted for the acid, completely different products were obtained – the reaction yields aminobiphenyls, indicating attack on carbon rather than nitrogen. One thing to keep in mind is that triflic acid has a Hammett acidity of -14.1, while TFA’s is -2.7; triflic acid is therefore about 1012 times more acidic than TFA! In addition, most people would expect that simply increasing the acidity would just affect the reaction kinetics, and that this would be subject to general acid catalysis. However, since the products and product distribution is completely different, a different reaction or mechanism is now involved.

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Prof. Olah’s insight was to propose that in a superacidic medium, positively charged cations (or “onium” ions) could undergo further interaction with the solvent to yield even more electron-deficient species. The nature of this interaction can vary anywhere from a hydrogen-bonding interaction to a complete protonation yielding dications or dicationic species in the limiting case. This is still an area of research, and it is quite possible that the observed effects could also be due to dielectric or field effects alone, with no contribution from protonation (since superacids are a high-dielectric medium). Prof. Olah dubbed this interaction of the superacid medium with onium ions protosolvation, and this general concept came to be called superelectrophilic activation.

superelectrophile_slide_3There are a couple of things to keep in mind here. The resulting species are known as superelectrophiles and are transient, short-lived, high-energy intermediates. Prof. Olah and his coworkers put a lot of effort into trying to characterize the protonitronium dication (HNO22+) by NMR and other methods, but these were largely unsuccessful. But just because an intermediate cannot be characterized, it doesn’t mean that it doesn’t exist at all; we now know that stability and reactivity are opposing properties, and that just because a particular species is amenable to isolation and characterization, it may not be the true reactive intermediate in the reaction coordinate.

The real proof of the existence of superelectrophiles comes from kinetic studies done with varying acidities. The rationale behind these studies is as follows: if the monoprotonated species is the key intermediate in the rate-determining step of the reaction, then the rate should level off once the acidity required for complete monoprotonation of the substrate has been achieved. If on the other hand, the reaction rate continues to increase with increasing acidity, then it is not the monoprotonated species that is involved in the reaction, but a diprotonated (or protosolvated) species.

superelectrophile_slide_4
The slide above shows some examples of this; the Friedel-Crafts hydroxyalkylation of benzaldehyde with benzene is particularly illustrative. The rate of the reaction increases dramatically with increasing acidity! Although the superelectrophile has not been characterized, one can use this kinetic data as support for its intermediacy. The nature of the superelectrophile is also up for debate; experimental data suggests that the O,O-diprotonated species is involved, while theoretical data suggests an O,C-diprotonated species.

This concept can therefore be used for the design of new electrophiles in Friedel-Crafts chemistry. Protonated moieties, substituents than can become positively charged (by protonation or ionization), or other highly electron-withdrawing groups can be used to activate carbenium ions nearby in the substrate towards reaction. N-halosuccinimides can be activated in superacid media and do halogen (“X+“) transfer to arenes; this reaction was investigated by Prof. Olah and can be carried out in BF3-H2O. BF3-H2O is a particularly interesting superacid; it was first discovered by Hans Meerwein and is probably the cheapest superacid available today (apart from anhydrous HF). It can be prepared by bubbling one equivalent of BF3 into ice-cooled water, and can be stored as a frozen solid and thawed when needed. In related chemistry, the nitronium ion can be activated in superacid in order to carry out nitrations of challenging substrates, such as nitrobenzene other nitrated aromatics (which are used in explosives and synthetic musks). Benzoyl esters can also be activated in superacid, giving protoacyl dications or diprotonated esters which can undergo condensation with arenes to conveniently yield benzophenones.

superelectrophile_slide_5

Currently, Prof. Douglas Klumpp (Northern Illinois University) is doing research in this area; he started as a postdoctoral fellow with Prof. Olah at the time he received the Nobel Prize. Prof. Klumpp has extended Prof. Olah’s concept to design new types of electrophiles and superelectrophiles, including novel condensations and domino reactions.

superelectrophile_fig_1

R. R. Naredla, C. Zheng, S. O. N. Lill, D. A. Klumpp, J. Am. Chem. Soc., 2011

Once these multiply-charged species are generated, new types of reactions can be designed based on charge-charge repulsion; this enables regioselectivity at a different position, such as an aryl carbon, similar to what Shudo did earlier with N-phenylhydroxylamine in TFSA.

This should serve as a brief introduction to this fascinating topic, and if you’re interested in reading further, there are several excellent manuscripts and reviews available, including a book Superelectrophiles and their Chemistry*.

*I’m not condoning the use of illegitimate PDFs – this was the first hit when I searched for “Superelectrophiles and their Chemistry”, so its not like nobody else would have found it anyway.

March 8, 2017

Rest in Peace, Prof. Olah

Filed under: Chemistry — sankirnam @ 11:54 pm

I just heard the news today that Prof. George A. Olah had passed away.

This affects me personally, as I did my PhD in his laboratories, and was the last student to actually do research in superacid chemistry and carbocations, which is what Prof. Olah received the Nobel Prize for.

Prof. Olah was truly a giant not just in Physical Organic Chemistry, or Organic Chemistry, but Chemistry in general. I don’t need to rehash what has already been inscribed in the annals of scientific history – Prof. Olah has written several autobiographical accounts of his life and his research career, and these do a much better job at explaining things than I ever could.

What I can say is that Prof. Olah’s approach to science was extremely rigorous, thanks to the education he received in Hungary prior to the Communist revolution. This rigor was carried into everything he studied in Organic Chemistry. Prof. Olah was also extremely fearless when it came to exploring new ideas in chemistry, and this quality stuck with him the rest of his life. He started his career off in a makeshift laboratory (which was pieced together in a balcony) in the Technical Institute in Budapest, where, much to the disapproval of his PhD advisor, he did work in fluorine chemistry, Friedel-Crafts chemistry, and superacid chemistry, the subjects that would be a recurring theme in his life.

Lately, there’s been a trend in popular media, whether it’s books, blogs, or news media, to pit foxes and hedgehogs against each other. Foxes are people who have a very shallow understanding of lots of topics, whereas hedgehogs are said to be people who have a deep understanding of one topic. All of these sources tout the superiority of foxes, claiming that they make better predictions due to the fact that they don’t get caught up on one idea. Ever since I first read about this in Nate Silver’s The Signal and the Noise, I was unconvinced, because I knew scientists who worked on one (or a few) big ideas for their entire careers. Prof. Olah was one such individual, and he truly made the case for the superiority of hedgehogs!

Prof. Olah’s modus operandi was to throw all his effort in one area until he was satisfied that he had learned as much as he could there. He would then collect all his manuscripts and write a large review either as an independent review article or as a book, and then move on to the next topic. In this fashion, he covered a large swath of chemistry, from synthetic methodologies, to carbocation chemistry, Friedel-Crafts chemistry, onium ions, nitration, and methanol. If you want to learn more about these topics, I wrote about them briefly here.

Prof. Olah was extremely organized and methodical in his approach to science, and this is revealed in his publications, the majority of which are in various series. He has a series of 300+ papers on “Stable carbocations”, 60+ papers on “Friedel-Crafts chemistry”, 200+ papers on “Synthetic methods and reactions”, and so on. Each of these papers is a gem. Prof. Olah’s command over English is impeccable, and the papers are all carefully written to make the science not just understandable but accessible. Prof. Olah also had the good fortune to get married to a fellow chemist, Judith Olah, and they published several papers in Friedel-Crafts chemistry together.

Prof. Olah was one of the few chemists to get a reagent named after himself – Olah’s reagent is a mixture of HF and pyridine that is much easier to handle than pure HF itself, since it is a liquid at room temperature. Prof. Olah also came up with the use of SO2ClF as a cosolvent for superacids, as well as discovering that the mixture of HSO3F and SbF5 could form an extremely powerful liquid superacid system convenient for studying carbocations. The oft-repeated story of how that mixture came to be called “Magic Acid” is something that doesn’t need to be told again here.

There are a few things that set Prof. Olah apart from other chemists, not just from his generation, but also the current generation. The first is that he was able to do Nobel-Prize winning work while not being at a top university (e.g. Harvard/Stanford/Caltech/MIT/Berkeley etc.)! This was always a matter of pride for him, and really does go to show the quality of his ideas and his thinking. The second was his concern to do research that was truly practical and addressed the problems facing humanity today, such as climate change and energy storage. It was due to this concern that he spent the last 2 decades focused solely on a pet idea – The “Methanol Economy”. He also developed the process of methanol “bi-reforming”, which is based on existing Fischer-Tropsch chemistry, in order to make it practical.

Of course, success always breeds contempt, and unfortunately Prof. Olah did have enemies in his lifetime. Plenty of older chemists will remember the scientific rivalry (bordering on animosity) between Prof. H. C. Brown and Prof. Saul Winstein, and after Prof. Winstein suddenly passed away in 1969, Prof. Olah took his place. Another injustice is that Prof. Olah was never invited to give a lecture at Caltech or Harvard University. This is unconscionable, given his scientific accomplishments in chemistry!

I am proud to belong to the scientific family of Prof. Olah (which extends back to Emil Fischer), and grateful to have had the opportunity to learn and practice organic chemistry in his laboratories at the Loker Hydrocarbon Research Institute, USC.

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My copy of Superacid Chemistry…

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…signed by all the authors, including Prof. Olah!

EDIT (3/9/2017): USC has issued a press release in memory of Prof. Olah, which is well-written and very detailed.

2nd EDIT (3/14/2017): C&EN has written an article in memory of Prof. Olah, and some of his former students and colleagues have commented online.

February 27, 2017

Classics in Organic Chemistry, Part IX

Filed under: Classics in Organic Chemistry — sankirnam @ 10:05 pm

Apologies for the hiatus, I’ve just been busy with getting settled into the routine of work while also juggling everything else going on in my life.

This next paper is one that I feel has not received the attention it deserves – it is incredibly groundbreaking and really should get the author, A. J. Arduengo, a Nobel Prize. Every October, I wait eagerly for the Nobel Committee’s decision in hope that Arduengo’s name comes up, but so far have been disappointed. Oh well… there’s still time for them to redeem themselves.

As students of organic chemistry know, carbon is unique among the elements in terms of the number and variety of stable bonds it can form with itself and other elements. This ability of carbon is central to life and biochemistry; no other element has these properties to the same degree that carbon does. While silicon is also tetravalent like carbon (and has provided inspiration to countless sci-fi writers), it polymerizes through Si-O linkages, forming polysiloxanes. Si forms bonds with itself with great difficulty, in contrast to carbon.

When undergraduate students learn organic chemistry, they are introduced to the concept of “arrow pushing”, which is a formalism that allows one to keep track of electrons – after all, reaction mechanisms are simply the rearrangement of electron pairs (e.g. σ bonds, lone pairs, and π bonds) relative to the nuclei. Most organic mechanisms proceed through carbon intermediates in a variety of oxidation states that students quickly become familiar with. The major ones are carbocations, carbanions, and carbenes.

Prof. G. A. Olah received the Nobel Prize in Chemistry in 1994 for the work he had done studying carbocations over the course of his (now 70-year) career. Prof. Olah’s big breakthrough was the isolation of carbocations – particularly the t-butyl cation, as stable, isolable species that were amenable to spectroscopic characterization (e.g. NMR and IR spectroscopy). This was a big deal at the time of discovery, because prior to that, chemists had proposed the intermediacy of carbocations as intermediates in acid-catalyzed organic reactions and rearrangements, but had not been able to conclusively prove their existence. Regular readers of this blog will know that I had the privilege of working under Prof. Olah and Prof. Surya Prakash, continuing research on new classes of carbocations – but that is not relevant to this discussion.

While carbocations have been isolated, free carbanions still have not been (at least to my knowledge). This also leads into a discussion on solvent effects and solvation. When carbocations are generated in the condensed phase in superacid media, one has to also consider the counterion, which is the conjugate base of the acid (e.g. SbF6). Is the anion also associated with the carbocation, and if so, what is the nature of the ion pair? These questions were studied by Prof. Saul Winstein at UCLA in the early 20th century, and he came up with the concept of the “intimate ion pair” based on solvolytic studies he had carried out in order to probe the the SN1-SN2 continuum.

In organic synthesis, when you want to generate a carbon nucleophile, you don’t actually use a “free” carbanion – instead, you use a pseudo-carbanion, and most common organometallics are exactly that (e.g. Grignard reagents and organolithiums). Grignard reagents and organolithiums are commonly employed as souces of nucleophilic carbon, but the C-Mg or C-Li bond is actually rather covalent. The ionic character increases as you go down the periodic table, and so C-Cs bonds would be expected to be very ionic. I haven’t looked much into organocesium chemistry, but since I have not heard much about it, I can safely assume that it is pretty esoteric – cesium is not the easiest metal to handle, since it ignites spontaneously in air.

Anyway, the main thing is that “free” carbanions have not really been isolated or studied the same way that Prof. Olah was able to study carbocations – perhaps there’s another Nobel Prize up for grabs there?

After carbocations and carbanions, the final carbon intermediate is carbenes. Carbenes are unusual in that they are formally neutral, and have properties of both carbocations and carbanions. They have an empty orbital like a carbocation, and also have a lone pair of electrons. The other complication is that what I just mentioned holds true for one particular spin state of carbenes; the empty orbital allows carbenes to have 2 potential spin states, namely the singlet and triplet states. When the lone electrons are paired, then it is said to be in the singlet state, and when the electrons are unpaired, then it is said to be a triplet species.carbenes

Carbenes are important species because of their utility in a variety of areas – most significantly, the Grubbs 2nd generation catalyst has an NHC (N-heterocyclic carbene) ligand, which confers extra stability compared to phosphines due to its ability to strongly donate electrons as well as engage in π-backbonding.grubbs_catalyst_2nd_generation

With that context, today’s paper is on the isolation of the first stable, crystalline carbene. This was carried out by A. J. Arduengo and coworkers at the DuPont Central Research and Development laboratories in Delaware in 1990. The DuPont laboratories were the place to be in the 20th century for cutting-edge chemistry research – they basically single-handedly revolutionized not just the field of chemistry, but the lives of everyone on the planet. It’s difficult to overstate the impact that DuPont’s research had; here’s a brief list:

  • Wallace Carothers in the 1930’s single-handedly developed the field of polymer chemistry while at DuPont, creating Nylon, Neoprene, and the concept of step-growth polymerization.
  • Roy Plunkett discovered Teflon by accident when he saw that the pressure in a cylinder of tetrafluoroethylene had dropped to zero. Upon sawing the cylinder open, he obtained a white powdery solid that was very chemically inert, had a low surface friction, and had a very high heat resistance. Plunkett became infamous for later developing Freons (fluorochlorocarbons which were extensively used as refrigerants due to their heat capacity, until Prof. Rowland (UCI) discovered that they were responsible for ozone depletion in the upper atmosphere) and tetraethyllead (which was used as an anti-knock additive for gasoline until it was realized how undesirable lead pollution is).
  • Stephanie Kwolek invented Kevlar while at DuPont, and showed that when woven, the strands of aramids were incredibly strong, thus leading to their use in bulletproof vests.
  • Charles J. Pedersen synthesized crown ethers while at DuPont, and showed that 12-C-4 had a high affinity for Li+, 15-C-5 for Na+, and 18-C-6 for K+. Pedersen later received the Nobel Prize in Chemistry for this work, and was one of the few recipients not to have a PhD!
  • Richard Shrock started his research career at DuPont investigating tantalum alkylidenes, which are metallic carbene intermediates in olefin metathesis. Shrock continued these investigations as a professor at MIT, and eventually received the Nobel Prize along with Prof. Robert Grubbs (Caltech) for his work in developing well-defined olefin metathesis catalysts.
  • F. N. Tebbe developed the eponymous Tebbe’s reagent for methylenation of carbonyl compounds. This led to the later development of the Petasis reagent, which I might cover later.
  • Norman Borlaug also worked at DuPont CR&D for 2 years, but did his major Nobel-Prize (and humanitarian) work afterwards. Norman Borlaug’s impact on humanity cannot be overstated; it’s mindboggling to think that just due to three people (himself, Fritz Haber, and Carl Bosch), we have been able to support an estimated extra 3 billion people on the planet!
  • T. V. Rajanbabu (now at OSU) and coworkers did some very elegant work in the 80’s developing a new polymerization method called group-transfer polymerization, and also demonstrated some very nice radical-mediated ring closures using Ti(III) reagents.

Arduengo’s work therefore follows a long line of high-impact research that was conducted by some of the best minds in the world at one of the most productive laboratories in the world! Shrock and Tebbe had done some carbene research at DuPont earlier, so there was a precedent for that. Arduengo generated the first stable persistent carbene by deprotonating the imidazolium species below. arduengo_1Catalytic DMSO is needed, and the actual base is the dimsyl anion, as NaH is basically insoluble in THF. In fact, NaH and THF reminds me of a spectacular gaffe by a research group in China that found its way into JACS in 2009 claiming the discovery of a NaH-mediated oxidation of secondary alcohols to ketones (which turned out to actually be mediated by peroxides in the THF or atmospheric oxygen).

The incredible thing is that the carbene so generated is stable and can be isolated in pure form. It can be recrystallized, and Arduengo was able to get X-ray diffraction data, as well as NMR data. The 13C NMR shows that C2 still has some electrophilic character even though it formally also has a lone pair. Part of the stability enjoyed by the carbene is due to the blocking provided by the very bulky adamantyl groups – in fact, the carbene can be melted and remelted without depression of the melting point!

As Arduengo concludes in the paper:

Carbenes have long been recognized as important reaction intermediates. The aggressive study of carbenes as reactive intermediates has provided much fundamental knowledge for chemical science. Until now there have not been any “bottle-able” carbenes, and we hope that the production of these stable nucleophilic carbenes will allow for convenient study of this class of compounds. We are currently investigating both the electronic structure and chemical reactivity of 1 and related isolable carbenes.

If NHC’s and related compounds are being used as versatile ligands in organometallic chemistry, organic synthesis, and as organocatalysts in their own right, it is all thanks to the seminal work of Prof. A. J. Arduengo. I sincerely hope that one day, he and his work get the recognition that is due.

Addendum: After all this, I hope you will share my disbelief that DuPont gutted the CR&D in 2015-2016.

February 22, 2017

View from the office

Filed under: Photography — sankirnam @ 10:48 pm

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Taken with my cellphone (Nexus 5) camera. Effects and filter done automatically by Google Photos.

January 28, 2017

Good news

Filed under: Chemistry Jobs — sankirnam @ 9:29 am

Regular readers of this blog will know of my struggles to find a job for the last two years. I finally have some good news on this front – I started a new job on Monday for a small consulting firm in Orange County. The work is challenging, but at the same time, interesting and rewarding. I also have the privilege of working alongside some extremely successful, accomplished, and intelligent people, so I am actually excited to go in to work each day!

I’m very happy that the position is local – one of my priorities was to stay in CA, not just for mrudangam but also given recent developments (the election and the US economy in general). For better or for worse, everything is getting concentrated on the coasts, and most tech/biotech jobs are either in the Bay Area or Boston – not being proximate to those areas can set you back in terms of job growth potential. In addition, I learned the hard way that networking is everything when it comes to getting a job – applying online is like playing roulette hoping that your resume gets chosen out of the pile out of 100’s/1000’s of others.

#chemjobs #thestruggleisreal

January 20, 2017

Farewell, Obama

Filed under: Life — sankirnam @ 11:16 am

Thanks, President Obama, for a remarkable 8 years. Your administration accomplished a lot, and even though it may seem that we do not appreciate your struggles (especially with a gridlocked partisan Congress), I hope history will be a lot kinder and that you do get the recognition you deserve. You were more than we, the American people, deserved as last November’s election showed. You can now take a well-earned break from public scrutiny – but please don’t disappear for too long, as we need your help in making sure all your hard work doesn’t get undone by the next President!

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Some links:

  1. An excellent article by President Obama for The Economist (Oct 2016) on the state of the US economy, and what challenges still lie ahead.
  2. Obama’s farewell address (I missed seeing this live on TV, so I have to watch it today in order to console myself over current developments):

  3. I did happen to see this one live – Obama awarding the Presidential Medal of Freedom to Vice-President Joe Biden!

     

  4. Obama’s State of the Union address from 2015! I particularly remember this speech as he was slightly snarkier than usual, and deservedly so. He also chastised Congress towards the end for being so partisan, and implored Republicans and Democrats to come together to generate solutions for the good of the nation.

January 17, 2017

Poromboke Paadal

Filed under: Carnatic Music — sankirnam @ 12:39 pm

This video has been trending on Youtube for the last couple of days:

One cannot fault TMK’s music – the music is beautiful, and his rendition is excellent, as always.

I just find it interesting that he is using Carnatic music as a medium for environmental activism, given that Carnatic music is an extremely niche art form. This may not be the optimal way to reach out to a lot of people with this message.

December 16, 2016

My experiences with learning “Data Science” in 2016

Filed under: Coding, Data Science — sankirnam @ 11:21 pm

Well, 2016 is drawing to a close…

This has been a weird year globally, with the death of a lot of influential people in history (including, among others, Muhammad Ali and lately J. Jayalalitha, the Chief Minister of Tamil Nadu, India), and some other strange political occurrences (Brexit and Trump getting elected). I haven’t posted here much because I have a million thoughts swirling around my mind all the time now, and finding a couple of hours of focused time in order to distill them down into an article on a single topic is a bit challenging. Nonetheless, there is something that I want to discuss today.

Firstly, I had the sobering realization a few days ago that it has been 2 years since I finished my PhD and I have nothing concrete to show for it; I’ve been unemployed for the past two years. Well, I’ve learned some valuable things about life and other topics which I wouldn’t have been able to learn otherwise, but it has been at a rather expensive cost: progress in my career.

In any case, one of the major themes of this year (for me) was that I made major progress in learning programming! I want to share what I learned so that others who are thinking of venturing down this path can learn from my experiences.

Firstly, my motivation in learning to code resulted in me being a little unfocused; I was unemployed and seeing a lot of people around me getting hired for cushy tech jobs with great salaries. Desperation shouldn’t be your only motivation for trying something. I was also unaware of the vast variety of “coding” jobs out there, and they can be quite different; CSS is considered “coding”, but it is vastly different from doing software development in C++, for instance.

I’m all for teaching computer science principles in the grade school level; the basics of control flow are not terribly complicated – it’s just logic, after all. Understanding looping, recursion, iterations, and conditionals does not require a very advanced background in any other subject, and knowing these will take you very far later on in life. I’m a strong believer that everyone should learn to code, given the increasing automation that is threatening all industries today. Those who can code will be the last people to have their jobs automated out of existence, pure and simple.

All this being said, I started my journey down this rabbit hole with Codecademy. I highly recommend this for others who also have no formal background in programming/CS, as it eases you into the relevant concepts of the language of your choice. It’s a great place to learn the higher-level languages (such as JavaScript, Python, and Ruby), but keep in mind that the courses are introductory, and very short (they can be completed in a few hours). They’re designed to give you just enough knowledge so that you can go out and keep learning on your own or from other sources.

After Codecademy, my next stop was FreeCodeCamp. FreeCodeCamp is amazing, and I hope it grows from strength to strength over time. It is the brainchild of Quincy Larson, and it attempts to create a fairly rigorous curriculum in Full-Stack Web Development starting from scratch; no prior knowledge is required, like Codecademy. The first lesson is literally “Hello World!”. It starts off with a comprehensive coverage of the front-end (website building with HTML and CSS), and also covers responsive design using Twitter’s Bootstrap API. It then progresses into JQuery and vanilla JavaScript, and it has you also do some pretty challenging algorithm challenges, which reinforce your understanding of all the methods and properties in JavaScript. The bonus with FreeCodeCamp is that it also has you working on projects, which can be incorporated into a portfolio so that you have something to show to prospective employers.

Web Development has the lowest barrier to entry among all the different types of programming, and that’s why places like FreeCodeCamp thrive. It was after doing it for a while that I realized webdev wasn’t for me, however; I don’t have the patience to mess around with DOM elements and get that alignment juuuuust right; if I really had to choose, I would be more comfortable doing back-end stuff.

I continued working on JavaScript and FreeCodeCamp while applying to programming bootcamps in April-May 2016, and eventually ended up taking a “Data Science” bootcamp by Logit in Hollywood. I wrote about it earlier,  so there’s no need to reiterate what’s already been said. I felt like “Data Science” would be the best fit, given what I had experienced with programming thus far, and also (naively) thought it would give me the best ability to leverage my PhD.

I used the word “naively” in the previous paragraph; here’s what I learned:

  1. Getting a job after a bootcamp is all about how strong your resume is prior to the bootcamp. Now, that may not seem fair, as people want to go to bootcamps to “reset” their careers and get a fresh start, but the reality is that you really can’t learn much in just 12 weeks. And now that bootcamps are getting more popular, employers are looking for other ways to distinguish you from the hundreds or thousands of other people who are also taking bootcamps. Sure, you took a JavaScript bootcamp, but what else stands out? Do you have an advanced degree (MS/PhD) or did you go to a top university (Harvard/Stanford/MIT/Caltech/CMU etc.)? Do you have relevant prior work experience?
  2. In “Data Science”, degrees in CS, math, statistics, computational fields (e.g. computational biology), biostatistics, or physics are extremely sexy. If you have one, flaunt it as much as you can! Any other degree (including my PhD in Organic Chemistry, as I discovered) is worthless in this context. That’s because “Data Science” is a poorly defined field and a lot of employers still don’t know what they want. If you look at job descriptions, most will require knowledge of a scripting language (R or Python), Java, a lower-level language (C or C++), thorough understanding of SQL, and Bash scripting (on Linux). These are not things you can pick up in a few weeks at a bootcamp.
  3. The “Data Science” market is cooling off right now. A few years ago, there was a massive hype surrounding “Data Science”, and there were numerous articles talking about how there was a critical shortage of “Data Scientists” in the country. My experiences have shown the opposite, however – it took one of my friends in my cohort (who has a PhD in physics, one of the “sexy” subjects I mentioned above), about 4 months to land a job after the bootcamp.

So – what useful, actionable advice can I give after all this? What I can say is that if you want to learn “Data Science”, all the material is available online for free. The advantage with a bootcamp is that it gives you a roadmap of what to study, as well as connections – to your classmates, instructors, and other people who the organization is affiliated with. Out of all the courses I’ve seen and taken online regarding “Data Science”, this progression is probably the best, and most logical (feel free to leave comments if you have other suggestions):

  1. Start with Codecademy if you have 0 programming experience. If you want to get into Web Development, complete the JavaScript, HTML, CSS and related tracks, and then dive right into FreeCodeCamp. Otherwise, if you think you may want to do Data Science or want to have a broader understanding of CS fundamentals, stick with Python.
    N. B. Something to keep in mind: if you have no prior experience with programming, don’t worry about R. R is a specialized language for statistics; it is written by statisticians for statisticians, and the syntax is very challenging even for experienced programmers.
  2. Once you’ve completed Codecademy, the next course I would take is MIT’s 6.00.1x Intro CS course on EdX. I have taken this course myself and I have written about it. This course gives you a fantastic intro to the fundamentals of computer science at a fairly rigorous academic level, and it uses Python as well, so that should give you more practice with programming in vanilla Python. The follow-up course 6.00.2x is also good and covers more advanced topics including algorithms, random walks, and other topics, which should put you in a good position to learn more about “Data Science”.
  3. HarvardX’s PH526x course on EdX is a good follow up to this sequence, since it introduces a lot of the popular Python packages for “Data Science” including numpymatplotlib, Pandas, and others. I also just finished the course earlier this week and will put my thoughts on it in a separate post here.
  4. Microsoft DAT210x on EdX is also highly recommended, and I also wrote about it after completing the course. This course gives plenty of practice with machine learning, and will put you in a good position to learn more about any of the algorithms in the course (K-Means, KNN, SVM, Random Forest, and others).

So – after taking all of these courses, THEN you can think about joining a bootcamp to further your knowledge. I wish I had done all the above courses before I did the “Data Science” bootcamp this summer; I would have been in a better position to learn, absorb, and better assimilate the material. But what’s done is done, and I’m continuing to learn Python, Machine Learning, and “Data Science” concepts at my own pace. I’m continuing to practice vanilla Python on Hackerrank, and you can follow my progress on my github – I’m trying to make github commits on a regular basis so that it makes a favorable impression on whoever happens to stumble across it! Interestingly, some of my repositories are getting a fair bit of traffic….so, you never know!

I sincerely hope that this rather “stream-of-consciousness” post helps you, if you do decide to venture down this path!

 

December 9, 2016

More recordings!

Filed under: Carnatic Music — sankirnam @ 8:15 pm

Shameless plug for a thani I played in a concert a few months ago here, on Diwali:

In retrospect, the sound quality is not bad, considering that I was playing without mikes – this audio is directly spliced from the video recording of the concert.

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