DAT Destroyer O Chem Flashcards
What is the tollens reagent
Ag(NH3)2
What does the tollens reagent Ag(NH3)2
they are oxidizing agents that convert aldehydes to acids
what is the equation for double bond equivalents
(2C + 2 - H - X + N) / 2
what reaction is caused by
PCC
——->
CH2Cl2
the oxidation of alcohol to an aldehyde or ketone
What is a grignard reagent
an RMgX
what does a grignard reagent do
the R group Nu attacks the Carbonyl carbon and attaches, forming an alcohol
What is an azeotrope
an azeotrope is a constant boiling mixture that is made up of substances in a certain ratio that simple distillation cannot separate
Where do radicals usually add
the most substituted carbon
how is conversion from glucose to fructose started
removal of the alpha H
what is a solvolysis reaction
when the solvent acts as a nucleophile
which has higher boiling points alcohols or ethers
alcohols
what is a constitutional isomer
same formula, different connectivity
what do electron withdrawing groups do to adjacent bases
make them less basic
which is more basic a lone pair in an sp3 or sp2 orbital
the lone pair in the sp3 orbital
What does ___ do
RCl
—–>
AlCl3
it adds the R (at least to benzene)
What does ____ do to a primary alkane
K2Cr2O7
————->
H3O+
converts it to a carboxylic acid
what does Br2/FeBr3 do
adds bromine
What does _____ do to benzene
HNO3
——–>
H2SO4
adds a nitro group
What are activating groups (electron donators)
2HN- (How nice of you to donate)
- OH (OH, you need some money)
- OR (OR i can give you food)
- R (Really, I’ll give you money
- aryl groups (Plate of food - its an aromatic group)
What are deactivating groups (electron withdrawers)
carbonyls SO3H (SO! I ain't giving you money) Cyanide (CN) is CNister NO2 (You want money, NO!) NR3 (No really, I'm not givin you money)
acivators and deactivators = o,p,m directors
Activators are OP directors
Deactivators are M directors
What does _______ do
I 2 excess
————–>
Oh-
it’s the haloform reaction
it removes a CH3 from a methyl ketone, replacing it with an O- group
what is heat of combustion
the heat required to break down the molecule
What does a high heat of combustion = less stability
because it does
Which has a higher heat of combusiton, the more or less substituted alkane
the less
What is the product of the claisen condensation
an anhydride
what does the dieckmann condensation do
cyclizes half of a diester
what kinds of molecules would easily be converted into a grignard reagent
those without acidic protons
what is the product of a benzylacid chloride and a benzoic acid
an anhydride with two benzyl groups
what does CH3CHOOOH do to alkenes
forms an epoxide
what does ______ do
C2H5OH
————–>
H+
the C2H5O- Nu attacks the more substituted carbon
What does ________ do
TsCl
——>
Pyr
the Ts replaces the H of an OH group (to be later replaced by another Nu)
how are bicyclo compounds named
- bridghead recieves C1
2. Numbers in parentheses indicate how many carbons are between the two bridgeheads
what things give positive tests with Br2/CCl4 and cold dilute KMnO4
things with double bonds (benzene doesn’t count, the double bonds are not normal due to resonance hybridization)
how many products can the chlorination of 2 methylbutane
6 (including stereoisomers)
which things favor which type of reaction Nucleophilic substitution Nucleophilic addition Electophilic addition electrophilic substitution
Esters and amides do Nu substitution
Aldehydes and ketones do Nu addition
alkenes and alkynes do electrophilic addition
aromatic compounds usually do electrophilic substitution
What does _____ do
LiAlH4, Et2O
——————->
H3O+
- reduces aldehydes to primary alcohols
- reduces ketones to secondary alcohols
- esters into primary alcohols
- carboxylic acids into primary alcohols
- doesn’t reduce double or triple bonds
what happens when you react an aldehyde with a amide
the carbonyl carbon of the aldehyde double bonds to the Nitrogen of the amide
what does K2Cr2O7/H do to a secondary alcohol
turns it into a ketone
what does (R)3 P+ -CH2/ DMSO do to a carbonyl
replaces the O with the R group
what does B2H2, THF / H2O2, OH- do to a double bond
anti markovnikov addition of OH to the double bond
What does 1) CH3 MgBr / 2) H3O+ do with esters
2 moles of the grignard will react with it to form a tertiary alcohol
what is a lactone
a cyclic ester
What happens when an aldehyde is reacted with dilute acid or a base
if it has alpha hydrogens it will do aldol condensation
What will Cl2(excess) /OH- do to a carbonyl
it will replace all of the alpha hydrogens
When can heating carboxylic acids result in decarboxylation
only when you heat a beta-keto acid (a carboxylic acid on the beta carbon of a Ketone)
what kind of reaction is a double dehydrohalogenation
E2
would R-CN be replaced by I- in a reaction
nope
What does a large sterically hindered base do to a carbonyl
it will remove the most accessable alpha H
if you have an acid with a pKa of 5, at pH 7 is it mostly the acid or the ion
ion
When do we create a carbocation
nitration sulfonation alkylation acylation halogenation
What happens when doing alkylation if you have 3 carbons or more in a linear fashion
it rearranges, and will bond a more substituted carbon
what does Br2/heat do when there is a C-h group off of a benzene ring
it will replace the benzylic H
what are exceptions to the rule that atoms bound to more electronegative atoms are electron withdrawing groups
NO = activating group Halogens = activating groups
Secondary and tertiary Amines are withdrawing groups even though they have less electronegative atoms after it
what does Zn(Hg)/HCL do to a carbonyl group
completely remove the carbonyl, turn it into CH2
what does 1) Sn, HCL/ 2) OH- do to a nitrobenzene
turns the nitro group into an amine (aniline)
why does Br2 and light, or NBS attack benzylic H’s
because that creates the most stable radical
what do peroxide initiators do
allow one to create a polymer
what does Br2/CH2Cl2 do to a double bond
adds Br to both sides of the double bond (reduces it too)
What is the order of best to worst leaving groups amongst the halides
I>Br>Cl>F
What is 3 benzene groups attached to a P with a lone pair going to do to a alkyl halide
replace the halide. then it is deprotonated by a strong base (Li) this creates a witting reagent.
What does the witting reagent do to a carbonyl
replaces the C=O bond with C=R(of the wittig reagent)
what is the order of polarity
least to most
alkanes alkenes ethers esters aldehydes and ketones alcohols carboxylic acids
what would H3O+ do to a lactone
lacone is a cyclic ester
it cuts it and OH adds to the carboxylic acid
what does the jones reagent do to alcohols
turns them into aldeydes and ketones
what do electron withdrawing groups do to acidity
increase it
what happens to amides when reacting with water
the NH group will be replaced by O- in basic conditions
the NH group will be replaced by OH in acidic conditions
