organic chemistry - How can an inexperienced chemist determine the chemical structure of a molecule?

I'm a fairly inexperienced, but nonetheless interested chemist, currently planning a small project for the coming summer: I want to isolate an unknown chemical from a plant and determine it's chemical structure.

I have ample access to Carex grayi, a sedge plant, and have chosen this plant for a few reasons.

1. Of the plants growing near where I live, I can definitively identify Carex grayi. I am relatively inexperienced in taxonomy and plant identification, and I want to know which species I am working with.


2. As far as I can tell, the plant is relatively unresearched, and may or may not contain alkaloids.

This brings me to my next point. I know it may seem immature or disheartening, but my interest in chemistry stemmed from my interest in neuroscience and neurotransmitters. From countless hours of reading, I have learned much about the pharmacological (and sometimes psychoactive) tendencies of alkaloids. I realize that ingesting unknown alkaloids is extremely dangerous, and I do not intend to ingest anything. However, due to their numerous applications in medicine and recreational use, there is a massive amount of information on the internet regarding their extraction and isolation. I am entirely open to the idea of isolating a chemical from another group, but as I am inexperienced and my interest stems from neuroscience, I only really know about alkaloids. I am only somewhat familiar with terpenoids, and know little about any other group.

So, assuming I am able to extract an unknown chemical of some specified group from a plant, is there any way for me to determine the chemical's structure? The Chemical structure Wikipedia page lists the following methods for determing chemical structure:

• X-ray diffraction


• Proton NMR


• Carbon-13 NMR


• Mass spectrometry


• Infrared spectroscopy

I don't really have access to these tools as student over the summer. I am willing to spend a small amount of money on this project, but no more than about one hundred dollars. Is it too much or too difficult for a student to determine a chemical's structure over the summer? Should I do anything differently (as in, is there a certain group of chemicals that would make this project possible or easier)?

Also, is there a "classical" chemical extraction similar to this that most fledgling chemistry students would conduct? This is obviously a ridiculous made-up example: extract dandylionine from a dandy lion flower.