chem 2325 exam 2 flashcards

my goat would've never stressed me like this

complete the following reaction

EAS - Halogenation of aromatic rings uses FeX3 or AlX3 (where X is Br or Cl) as a catalyst to brominate/halogenate at ortho or para positions

what is unnatural about halogens regarding their electron-donating/withdrawing status and where they add on aromatic compounds?

they are considered electron-withdrawing (well both), but add at ortho or para positions like electron donating groups

complete the reaction

EAS - nitration. replaces a hydrogen atom on an aromatic ring with an NO2 group to form a nitroaromatic compound using HNO3 and H2SO4

complete the reaction

sulfonination (EAS) - SO3 and H2SO4 react to form an SO3H group off an aromatic compound, replacing the H with SO3H

complete the reaction

Clemmenson reduction (EAS). Zn (Hg) in HCl, also called Zinc Amalgam, reduces aldehydes and ketones to their corresponding alkyl groups. this is like an acidic version of Wolff kishner

complete the reaction

Wolff-Kishner converts aldehydes or ketones into alkanes by deoxygenating the carbonyl group. similar to Clemmenson reduction. this is like a basic version of Clemmenson.

complete the reaction

Friedel-Crafts acylation. combines a R-CO-X (where X = halogen) group with a benzene/aromatic compound to add a ketone group to it. the bond occurs where the halogen was bonded to

complete the reaction

Friedel-crafts alkylation - attaches an alkyl group to an aromatic compound using EAS. it uses AlCl3 or FeCl3 as a catalyst. bond replaces the position where the chlorine was

complete the reaction

gatterman-koch. it uses CO, HCl in AlCl3 to replace a hydrogen on a benzene carbon with a H-C=O group.

complete the following reaction

nitrobenzene reduction. uses metal (Fe, Sn, Zn) and acid or Pd, Pi, Ni catalyst H2 to convert a nitro group into various nitrogen containing groups

complete the following reaction

catalytic hydrogenation. adds H across unsaturated carbon-carbon double bonds to create a saturated alkane

complete the following reaction

witting reaction. converts an aldehyde or a ketone into an alkene using a phosphorus ylide (wittig’s reagent). it combines the two reagents where the =O used to be and forms a double bond there.

complete the following reaction

Suzuki coupling - reacts organoboron reagent and organic electrophile (like an organohalide) to form a C - C bond.

complete the following reaction

heck reaction. very similar to Suzuki, breaks the C-Br and C-H bond and bonds together the two structures in a carbon carbon bond

can also use Pd(PPh3)4

complete the following reaction

Corey-house. reacts a culi reagent with an alkyl halide to form carbon carbon bonds

complete the following reaction

while this typically performs strong/harsh oxidation and creates a carboxylic group at a benzylic position, when reacted with a phenol, it produces a 1,4-quinone structure.

complete the following reaction

primary alcohols react with carboxylic acids to form an ester compound and h2o byproduct

complete the following reaction

kmno4 performs harsh oxidation. it identifies benzylic carbons and turns the first carbon into carboxylic acids, regardless of how long the chain is.

this only works if at least one hydrogen is present on the carbon, otherwise no reaction will occur

this can also be done with na2cr2o7

complete the following reaction

birch reduction - uses NaNH3 in tbuOH or another alcohol to create non conjugated double bonds on a formerly aromatic structure

ethanol and water can also be used instead of tbuOH, but tbuOH is ideal because of the bulkiness and steric hindrance

may be 2 or 3 minor reactions missing