DAT Orgo forgettables

what does Na₂Cr₂O₇ oxidizes primary alcohols into?

carboxylic acids

what does Na₂Cr₂O₇ oxidizes secondary alcohols into?

ketones

ortho/para directors

(things with lone pairs) -NH, -OH, -OR, -R (alkyl), -benzene ring

meta directors

(things with a double bond to O) -NO2, -CN,

what is another name for asymmetrical carbon

chiral center

protic solvents

solvents that have H atoms bonded to O, N, or S. Examples include: CH₃OH, CH₃CH₂OH, CH₃COOH, H₂O

aprotic solvents

do not react with nucleophiles, so that they can proceed down the S_N2 or E2 pathway. Examples include: DMSO, acetone, DMF, THF, ether

what type of solvents do S_N1 and E1 reactions prefer?

polar protic solvents

what type of solvents do S_N2 and E2 prefer?

polar aprotic solvents

is NO₂ an ortho/para or meta director?

meta director

Is NH₂ an ortho/para or meta director?

ortho/para director

what is the rate for S_N2 reactions?

methyl > 1 > 2 > 3

what type of reactions use aprotic solvents?

E2 and SN2

are meta directors electron withdrawers or donors?

withdrawers

do meta directors increase or decrease acidity?

increase acidity

are ortho/para directors electron withdrawers or electron donors?

electron donors

do ortho/para directors increase or decrease acidity?

decrease acidity

is CH₃ an ortho/para or meta director?

ortho/para

aldol condensation

combines two carbonyl groups to form a beta-hydroxyl carbonyl

what is required for aldol condesation to occur?

an alpha hydrogen

what is an alpha hydrogen?

a hydrogen bonded to a carbon that is immediately adjacent to a carbonyl carbon.

what do these reagents make?

a syn diol (two OHs facing the same direction as each other)

what do these reagents make?

an anti diol

what are swern oxidation and PCC do?

they are oxidizing reagants that change primary alcohols to aldehydes and secondary alcohols to ketones

what are these

meta directors

what are these

ortho/para directors

what do electron withdrawing groups (meta groups) do?

draw electron density out of the aromatic pi-system, thereby decreasing the reactivity of the benzene (deactivate rings)

what do electron donating (ortho/para) groups do?

make an aromatic ring more reactive

thermodynamic product

the major product at higher temperatures

which type of reaction gives a stereochemical inversion of the configuration?

SN2

degrees of unsaturation

number of pi bonds + number of rings

which type of solvents are favored for SN2 reactions?

polar aprotic solvents

what does H2, Lindlar do?

converts an alkyne to a Z-alkene

what does Na, NH3 do?

turns alkyne into E-alkene

what does this do

makes a carboxylic acid

what does this do

convert secondary alcohol to a ketone

the more s character…

the more acidic

electrophilic aromatic substitution

a type of chemical reaction in which an atom, usually a hydrogen, attached to an aromatic ring is replaced by an electrophile

electrophile

has atom with + charge, has electron withdrawing group

nucleophile

has a - charge, has nonbonding electron pairs

what is true about SN1 reactions and aromaticity

aromatic compounds undergo SN1 reactions faster than anti-aromatic compounds because they are much more stable

wolff-kishner

treats a ketone or aldehyde, reduces all the way down to CH₂

how do you determine which nucleophile is strongest?

whichever one has the strongest, most concentrated lone pair with no resonance stabilization

decantation

the process of tilting a mixture to pour out the top layer without disturbing the bottom layer. This only works if you have two immiscible components

recrystallization

process used to purify solid compounds. If you have a solid dissolved in a liquid, you could use recrystallization to heat the solution, then gradually cool it to precipitate the solid out

what does this reagent do?

puts an OH and ester on the same molecule

the higher the energy conformation…

the less stable the compound is

what does this reagent do?

creates a ketone

extraction

a procedure used to separate substances based on their solubility in different aqueous vs. organic solvents

what is this

non-aromatic

Which of the following is the most basic?

H₃C^-