midterm 1 reaction reagents

reagents for nitration

HNO3, H2SO4

reagents and purpose for wolff kishner

NaOH, (NH2)2, heat ; purpose is to eliminate a carbonyl’s oxygen

how to bypass the drawbacks of FC alkylation

do FC acylation then wolff kishner to eliminate carbonyl’s oxygen

reagents for sulfonation

H2SO4, heat —> product has an added SO3H

reagents for iodination

I2, H2O2, H+

reagents to change NO2 to NH2

H2, Pd/C

reagents to change R group to carboxylic acid

H2CrO4

benzene to cyclohexane reagents

H2, Ni

reagents for wolff kishner (completely get rid of carbonyl’s oxygen)

(NH2)2, NaOH

reagents to change Br to R group (aka Suzuki rxn)

R-B-(OH)2, Pd, base

reagents to change NH2 to N≡N (before sandmeyer can occur)

NaNO2, HCl

what occurs when a benzene reacts with a diazonium ion

azo coupling occurs and an azo compound (-N=N- functional group in between the two benzene rings) is formed

reagents for ozonolysis (reduction)

1.) O3, -78C 2.)(CH3)2S (aka dimethylsulfide)

reagents to reduce acyl chloride into aldehyde

1.) LTBA 2.) H2O

reagents to reduce ester into aldehyde

1.) DIBAL, -78C 2.) H2O

reagent for secondary OH to ketone

H2CrO4

reagent for primary OH to carboxylic acid

H2CrO4

reagent for primary OH to aldehyde

PCC

reagents for primary alcohol to carboxylic acid

H2CrO4

reagents for aldehydes to primary alcohols and ketones to secondary alcohol (and C≡N to single bond)

H2, raney ni

reagent for acetal breakdown/reversing cyclic acetal into original cyclohexane-ketone structure)

an acid (eg. HCl, H3O+)

rank the reducing agents (via providing hydrides) for carbonyl derivatives from strongest to weakest

LAH (aka LiAlH4), NaBH4, DIBAL, LTBA (aka LiAlH(Ot-Bu)3)

what are the reversible nucleophiles learned so far

-CN, H2O, HOR

examples of irreversible nucleophiles learned

hydride ion (H-), carbanion (CH3-)

reagents to convert ketone to cyanohydrin

KCN, HCl

reagents to convert ketone into a hydrate

H2O (with either acid or base catalyst)

reagents to convert a ketone into an acetal

2 eq of HOR, H+ catalyst

reagents to make a grignard reagent

Mg0, EtO2, 35C

organolithium reagents (strongest of organometallic reagents; changes halogen substituent to Li)

R-Li

order of substituents for pre sandmeyer to end of sandmeyer

nitrate (with HNO3, H2SO4) then change to NH2 (via H2, Pd/C), change to diazonium salt (via NaNO2, HCl), then change to halide (via CuX)

reagents to change NH2 to diazonium salt

NaNO2, H-X

list hydrides from strongest to weakest with their uses

• LiAlH₄ (LAH): reduces everything to alcohol

• NaBH4: mild, reduces aldehydes and ketones to alcohols

• DIBAL: reduces esters to aldehydes

• LTBA: weak, reduces acyl chlorides to aldehydes

grignard reagents (middle strength of organometallics)

R-MgX

gilman reagents (weakest strength of organometallics; replaces halogen with R group)

R2CuLi

reagents for suzuki (couples R groups)

RB(OR2), L2Pd, base

key feature of generation of electrophile for bromination of benzene

generate FeBr5

key feature of generation of electrophile for nitration of benzene

make HNO3 have water LG to leave and generate +NO2

key feature of generation of electrophile for sulfonation of benzene

use to H2SO4 to generate H2O good LG to leave and generate +SO3H

key feature of generation of electrophile for FC acylation

Cl that never quits and generates acylium ion R+C(O)

key feature of generation of electrophile for FC alkylation

Cl that never quits and generates R+

rank organometallics from strongest to weakest

1.) organolithium (R-Li)

2.) grignard (R-Mg-X)

3.) organocuprates (R2CuLi)