Currently in Organic I and I'm struggling to understand what solvents make good...

BunnyJinx
BunnyJinx

Currently in Organic I and I'm struggling to understand what solvents make good bases/nucleophiles and which ones are used for SN2 vs E2. Watched a bunch of videos but I still don't have a good grasp of it, even though the mechanisms and synthesis parts are easy for me.

General O. Chem bitching thread.

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All urls found in this thread:

sigmaaldrich.com/catalog/product/aldrich/308102?lang=en&region=CA
sigmaaldrich.com/catalog/product/aldrich/369527?lang=en&region=US
pubchem.ncbi.nlm.nih.gov/compound/N_N-Dimethylhexylamine#section=Top

Sharpcharm
Sharpcharm

Just got back my midterm Orgo II exam with a horrid grade. It's literally memorization at this point isn't it? I miss Orgo I

eGremlin
eGremlin

t. brainlets

King_Martha
King_Martha

I always had this mental model that as bulky bases cause elimination rather than substitution, ordinary bases in polar protic solvent act the same way, making a solvent shell which sterically hinders and prevents it from substituting the electrophile.

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StrangeWizard
StrangeWizard

"learning" [general] organic chemistry is almost useless and the only way to find out
what solvents make good bases/nucleophiles and which ones are used for SN2 vs E2
is to carry out many experiments on different substrates

realistically, there's not such thing as "good solvent", it depends on nucleophile used and substrate.
books often say that DMSO and DMFA are the best solvents, but workup may be a hassle if you are working with significant masses, and in some cases they are just too polar. I had once MTBE give the best yields for substitution

t. aced orgo, but found out how useless it is in practice two years ago

Gigastrength
Gigastrength

literally

TreeEater
TreeEater

Organic in 3-D Chemistry
fuck you and this picture

SniperGod
SniperGod

When are you nerds going to cook me some meth

TalkBomber
TalkBomber

soembody post a math version of this meme

PurpleCharger
PurpleCharger

Memelet

hairygrape
hairygrape

Any Medfags in here? I'm kinda curious how much of this knowledge I have to retain in my career.

lostmypassword
lostmypassword

good bases
weak conjugate acids. more so with negative formal charge
(pyridine, trialkylamines, LDA, hydroxide, tert-butoxide, methyllithium, amide, etc)
good nucleophiles
readily available lone pairs and lack of steric hindrance
(hydroxide, water, ethanol, halides, methyllithium, ammonia, amide, etc)
a lot of molecules are both good nucleophiles and bases, some are one and not the other, and some are neither. Sorting them into these categories based on general principles is pretty trivial. Methanol does not make a very good base in most cases because its protonated form has a low pka. Try to think about it in terms of stability of products/intermediates/reactants for a given pathway as well as steric effects

Methshot
Methshot

Absolutely none of it.

Emberburn
Emberburn

I'm in medical school as well. this guy is correct

Snarelure
Snarelure

are you literally me

RavySnake
RavySnake

Thanks for being part of the problem in today's medical field

New_Cliche
New_Cliche

help me doc, I got shot!
let's analyze the chemical structure of your clotting factors

Dreamworx
Dreamworx

help me doc I got shot
wait sorry I mean nurse because doctors don't do shit anymore

viagrandad
viagrandad

R thee me?

massdebater
massdebater

Was chirality covered yet? That was cool. The entire rest of the semester preceeding it was a memorization marathon. Rough.

Booteefool
Booteefool

Veeky Forums idk where to turn. I'm stuck with this online program that is brutal in how you input IUPAC naming.

What the fuck do they want?

N,N-dimethylhexamine is my best answer, but I've tried many combos.

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MPmaster
MPmaster

should be N,N-Dimethylhexylamine, your online program is pretty picky.

sigmaaldrich.com/catalog/product/aldrich/308102?lang=en&region=CA

haveahappyday
haveahappyday

I was good on my answer, and then checking sigma aldrich I found this which confirmed my theory, but that it is just a longer akyl.

sigmaaldrich.com/catalog/product/aldrich/369527?lang=en&region=US

The answer you gave wasn't accepted.

Deadlyinx
Deadlyinx

well fuck that shit then, damn. If you have unlimited tries you can give all these a go:
pubchem.ncbi.nlm.nih.gov/compound/N_N-Dimethylhexylamine#section=Top

But I thought that one was the IUPAC accepted.

TreeEater
TreeEater

Well fuck my ass and call me Lachatlier.

N,N-dimethylhexan-1-amine was the answer from that page. I swore I tried that combo.

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Evilember
Evilember

Lots of people bitching about orgo being irrelevant to their field are often wrong, but IUPAC naming is the one thing that is truly useless
t. chem phd, things need to be named in a way that can be easily communicated between people.

RavySnake
RavySnake

I love chem. O-chem is useful and gives me some drug nerd skills. It can be annoying, but as someone who semi-enjoys it I can see how other students want to kill themselves.

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Booteefool
Booteefool

OP here. Pretty sure I got over a 95 on this test, possibly over 100 thanks to the 7 point extra credit for identifying oleic acid and knowing it comes from olives.

That was actually pretty helpful, thanks.

WebTool
WebTool

drug nerd skills
Nice, reading erowid as a teenager was how i got into chemistry in the first place.

TechHater
TechHater

why does math have no funny meme's?

Ignoramus
Ignoramus

"solvent shell" image a good

AwesomeTucker
AwesomeTucker

t. someone who's never seen a real trauma get worked on
Shits insane. Trauma docs are crazy and 10 of them will just magically appear in the bay if they smell blood.

iluvmen
iluvmen

Because it's a humorless field full of people who are dead Inside.

Burnblaze
Burnblaze

Brainlet art student who wants to switch major to biology.

Will I be able to learn this or am I fucked?

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Nude_Bikergirl
Nude_Bikergirl

Your concept of spatial arrangement might give you an edge in visualizing molecules, but stuff like Genetics is going to fuck you pretty hard most likely. That and I can guarantee you aren't used to spending this much time practicing chemistry problems and understanding it past memorization. It takes more work than smarts though, so give it a shot if you are willing to work your ass off.

CodeBuns
CodeBuns

The whole point of the class is to prove you can catalog and understand large amounts of information rapidly and correctly. If you struggle with organic and think it's all about memorization (besides nomenclature) you should not consider medicine as your career.

No one is going to suddenly jump up from an operating table and scream
Which is the stronger nucleophile!?
But you're going to need to learn how to hold onto and understand a metric fuckton of information and organic chemistry are literal baby steps towards what medical school requires.

Raving_Cute
Raving_Cute

I'm aware of the way med school makes you drink from a firehose. But Organic at least prepares you to learn drug chemistry which is applicable to medicine. But your argument is often touted by Calculus professors as an excuse to take their worthless class. "Hurr it's critical thinking and problem solving!" So is literally every other college science class you pencil neck motherfucker! Fuck calculus and fuck physics 1. /rant

hairygrape
hairygrape

Brainlet detected

Playboyize
Playboyize

I want to be a doctor but also know as little as possible

PackManBrainlure
PackManBrainlure

all u need

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