OCHEM exam 2 unit 16

1) BH3 2) H2O2

solvents needed to turn c-c triple bond into aldehyde

DIBAL-H and H2O workup

solvents needed to turn ester into aldehyde

PCC

solvent need to turn primary alcohol into aldehyde

1) O3 2) DMS

solvent needed to turn double bond C into aldehyde

CuCH3 H2O workup (need weaker metal, not Li or MgX)

solvent needed to turn acid chloride into ketone

AgSO4 H2SO4 H2O

solvent needed to turn c-c triple bond into ketone

-al

ending of IUPAC for aldehyde on chain

-carbaldehyde

ending of IUPAC for aldehyde on ring

-one

ending of IUPAC for ketone

PCC

solvents needed to oxidize 1 degree alcohol to aldehyde

DIBAL-H then H2O

solvents needed to reduce an ester to an aldehyde

1) LiALH(CO(CO3)3)3 2) H2O

solvents needed to reduce acid chlorides to aldehyde

1) R2BH 2) H2O2, -OH

solvents needed to turn alkyne (triple bond) into aldehyde

1 degree alcohols, esters, acid chlorides, and alkynes

what are aldehydes prepared from

2 degree alcohols, acid chlorides, and alkynes

what are ketones prepared from

CrO3 or NaCr2O7 or PCC

solvents needed to oxidize a 2 degree alcohol into a ketone

1) R'CuLi 2) H2O

solvents needed to turn acid chloride into ketone

AlCl3

solvent needed to perform friedel crafts acylation into a ketone from an acid chloride and other organic compound

H2O H2SO4 HgSO4

solvents needed for hydration of an alkyne (triple bond) to a ketone

O3

additional solvent to make aldehydes and ketones with oxidative cleavage of alkenes

nucleophilic addition to the carbonyl carbon

general reaction that aldehydes and ketones undergo

acid catalyst

what is needed for nucleophilic addition at aldehydes or ketones if the nucleophile is more neutral?

protonation of carbonyl oxygen

first step of a reaction involving a carbonyl group and a strong acid

NaBH4, CH3OH, or 1)LiAlH4 2) H2O

solvents for carbonyl into primary alcohol and H

1) RMgX or RLi 2) H20

solvents for carbonyl into primary alcohol and R

CH3CN and HCl

solvents for carbonyl into primary alcohol with CN

Ph3P+--CR2

solvent for carbonyl into alkene with Rs sticking off double bond

RNH2 and mild acid, then H2O

solvent for carbonyl into imine (C=N)

R2NH and mild acid, then H2O

solvent for carbonyl into enamine (C=C-NR2)

ROH, H+

solvent for carbonyl into acetal (two OR groups where C=O used to be)

a 1 degree or 2 degree alcohol

result of treatment of aldehyde or ketone with either NaBH4 or LiAlH4 followed by protonation

a 1, 2, or 3 degree alcohol with a new C-C bond

result of treatment of aldehyde or ketone with either an organolithium or Grignard reagent followed by water

adds the components of HCN across the C=O

treatment of aldehyde with NaCN and a strong acid such as HCl

treatment with a base (deprotonation followed by elimination of CN)

how to reconvert a cyanohydrin to a carbonyl compound

heating with aqueous acid or base (H2O)

how to hydrolyze a cyanohydrin to a carboxy group (COOH)

Ph3P=O

result of wittig reaction (additional product)

1) SN2 reaction of Ph3P with an alkyl halide to form a salt 2) deprotonation of salt with strong base to form ylide (has free elections on a carbon)

two steps for Wittig

unhindered alkyl halide

preferred wittig reagent is derived from an

organic nitrogen compounds that contain a nonbonded electron pair on the N

define amine

imine

result of treating an aldehyde or ketone with a 1 degree amine

how many R groups it is bonded to

how is degree of amine determined

N=C

critical part of an imine

RN-H2 and mild acid then H2O

solvents needed to turn aldehyde or ketone into imine

C=C-NR2

critical part of an enamine

nucleophilic addition of 2 degree amine followed by elimination of H2O

mechanism for enamine from ketone or aldehyde

R2N-H and mild acid, then H2O

solvents needed to turn aldehyde or ketone into enamine

hydrolysis with a mild acid (H3O+)

how to convert imine or enamine back into carbonyl

H2O then H+ or OH-

solvents needed to turn carbonyls or aldehyde into two OH groups (works best with carbonyls or with aldehydes with electron withdrawing groups)

converts H2O to a-OH a stronger nucleophile

how a base hydrates a aldehyde or ketone to 2 OH

protonates carbonyl group, making it more electrophilic and more susceptible to nucleophilic attack

how an acid hydrates an aldehyde or ketone to 2 OH

two equivalents of alcohol

what do aldehydes and ketones react with to form acetals (carbon bonded to 2 OR)

1) CH3OH 2) TsOH

solvents needed to turn aldehyde or ketone into acetal

acetal

image is of what functional group

hydrolyzed by treatment with aqueous acid

how does an acetal become an aldehyde or ketone again

HO------OH and TsOH

how to turn a carbonyl into a ring to protect it

1) H2O 2) H+

how to remove the ring to turn it back into a carbonyl

only the hemiacetal group reacts to form an acetal

what happens when a compound with both an alcohol OH and hemiacetal OH is treated with an alcohol (when the OH is connected to a C connected to another O)