Chem exam 2-2 Flashcards
IUPAC name for methylacetate (ester is split personality - 2 names)
methylethanoate
ester is…(ester in the OC OC)
OCOC
amidation (amidation of a box and ammonia)
making amides - carboxylic acid with NH3, NH2, or NH
amides and amines are basic or acidic?
basic
amide or carboxylic acid higher bp?
amide - really high
amines or amides are more basic?
amines - BC the carbonyl group on amides is not an electron donor
naming amides (am I’d going to have to split the C and N?)
the part attached to the C=O ends in amide, ie - butanamide - anything attached to the NH is a substituent - name it N-akyl, like N-methylbutanamide
naming ethers (ether split in half and name)
it’s just C-O-C - no double bond. Double bond is ester. ethyl methyl ether.
when naming ethers…(ether one side and the other in alphabetical)
neither side has priority - it’s alphabetical - ethyl methyl ether
if a branch is O-CH3 it’s called…
methoxy - oxy at the end
remember - amides will have an….
O - so it may be written like CONH2
naming esters (I ate my ester)
the left side starting with the C=O is the acid, so name it oate. The right side is first.
The right side starting with the C is the akyl group - so methyl, etc.
naming esters
the right side is first, the left side second ending in ate.
difference btwn aldehydes and carboxylic acids
aldehydes have C (double bond) OH, and carboxylic acids have COOH, or C(double bond) O, OH group.
aldehydes end in…(AL-dehydes)
al.
a low pKa is more or less acidic than a high pKa?
a low pKa is more acidic
DON’T forget the C bonded to the..
=O
common name for propanedioic acid?
malonic acid
IUPAC name for carboxylic acid when it’s added to the end of a ring (lord of the rings gets the full box)
has carboxcylic at the end - ie - cyclopentanecarboxylic acid
if you see an amide that looks like this -
C-C - N
||
O
just ignore the O when naming, it’s still just an amide. So ethanamide
amines with 5 carbons are still…
water soluble
geometry of amines is..(amine is in Egypt)
trigonal pyramidal
when naming amines, any substituent off of the N will be named…
N-akyl, ie - N-methyl
amines are acids or bases? (am I on base?)
bases
common naming system (ethyl is so common)
will be ethyl, methyl. IUPAC will be numbering the chain
formic acid (formica HiCOOH)
HCOOH
when the OH group is removed from carboxylic acid, it’s called
oyl, ie - benzoyl group
add dioc to the end of the name if…
there are 2 carboxylic groups, ie butanedioc acid
low weight unsubstituted amides (NH2) are…(state of matter also)
solid (except formamide) and they are soluble in water and organic solvents
when naming ketones the common way, remember…(key out the C)
it's split in half, but you DO NOT count the C attached to the O. The O || C is like an independent group.
addition reactions with ketones and aldehydes is…(add water to the hyde in the keys)
just the addition of water (the H bonds with the O, and the O and the other H bond with the C, and the double bond is gone.
hemiacetals and hemiketals are formed when…(hemi alchy)
alcohol is added to ketones and aldehydes
what has to be added to an alcohol and ketone or aldehyde to form an acetal or ketal?
acid catalyst
REMEMBER, benzyl is..(benzyl my methyl)
benzene with CH2 attached
if you have phenyl ether or diphenyl ether…
it’s just 2 phenyls with an O in the middle. the carbons are there but you don’t need to draw them
if you’re drawing an aldehyde it should look like this…
O
||
C \ H
don’t forget to count the C attached to the____on an aldehyde
=O
the ONLY time you don’t count the carbon is when…
it’s attached to ketone and you’re doing common naming (split in half)
remember, if you’re using IUPAC to name ketones…
count all of the carbons in the chain
boiling points from highest to lowest - ketones, ethers, alcohols
alcohols, ketones, ethers (the double bond makes the bp higher for ketones and aldehydes)
if you see a formula with carboxylic acid plus an OH somewhere and heat and H+ it’s…
esterification. THEN you just take the OH off of the caboxylic acid and add it with one H from the other alcohol and move it over to make + H2O. Combine the rest of it to make O-CH3 at the end.
if see a formula with something plus NH2, it’s…
amidification. You simply take one H from the NH group and combine with the OH to make + H2O. Then add the remaining NH to the C on top
only use N or N, N with..
amines and amides
when naming amines…
anything coming off of the N is a substituent - so it would be named yl, like cyclopentyl amine
when naming amines, if you see a benzene with the NH attached, REMEMBER to name it
aniline
all amines can form what bonds?
hydrogen bonds, BUT only primary and secondary amines can hydrogen bond with each other.
which has the highest bp? alkanes, amines or alcohol?
alcohol first, then amines, then alkanes
amines plus water are…
weakly basic because the form -OH (the H from water joins with NH2 to make NH3) and the O and H from water form to make + -OH)
amines are acids or bases?
bases - because the lone pair of electrons on the H can form an H+ bond with acids or water
a base ___a hydrogen
accepts
if you have an amine attached to 4 other things (quatranary) name it..
ammonium ion at the end
naming amines - if there are no branches, it’s just
amine - ex. ethanamine is CH3CH2NH2. IF there are branches, then it’s N-alkyl amine
when trying to identify esters, carboxylic acids, and amides..
they are all carbonyl groups, they just have different things attached to the C=O. Ester has C-O attached, amide NH and carboxylic - OH
carboxylic acid - can it H bond with itself?
yes, and it’s liquid at room temp
H2C=CHCOOH name
propenoic acid
remember - if a carboxylic acid is attached to ring, cyclic structure, name it…
carboxylic acid, ie. cyclohexanecarboxylic acid
if you see benzene w/ NH2 and carboxylic acid attached (COOH) name it…
amino benzoic acid - not analine
small alcohols, Small acids, Amines and amide are or are not water soluble?
they can be dissolved in water
aldehyde and ketone intermolecular forces
dipole-dipole
aldehyde and ketone - hydrogen bonding?
not with each other but can with water
intermolecular forces amines
dipole dipole, and primary and secondary can hydrogen bond with themselves
carboxylic acid - intermolecular forces and hydrogen bonding?
dipole dipole and can H bond with themselves
intermolecular forces - esters and H bonding
they are dipole dipole and can’t H bond with water bc they don’t have an H
amide intermolecular forces and H bonding
dipole dipole and have highest BP bc the N and H’s can bond with water and themselves
Hydrogen bonding w/ amides
just 1st and 2nd, tertiery doesn’t have H to bond with
Polar dissolve in…
polar solvent such as water
The ability to make H-bonding increases the…
solubility in water
can be dissolved in water (5A K can dissolve)
small alcohols, Small acids, Amines and amide, ketones, aldehydes - all small
the more H to bond with, the..
higher the bp
highest BP Alcohol, carboxylic acid, amines and aldehydes?
carboxylic is highest bc it can H bond with itself - so strong that the bp increases
BP in order - everything! lowest to highest
Boil the sake
The As, HAKE ACAA
alkane-alkene-alkyne (dispersion forces) –> halogens, aldehydes, ketones, esters (dipole-dipole only since hydrogen is only bonded to carbon)—> alcohols, carboxylic acids, amines, amides. (hydrogen bonding).
last 4 bps - lowest to highest (ACAA)
alcohols, carboxylic acids, amines, amides.
if BP is below room temp, it’s a…
gas
