Organic Chemistry II: Exam 3 - Important Reagents

LiAlH4 reduces an aldehyde to a...

1° alcohol

LiAlH4 reduces a ketone to a...

2° alcohol

LiAlH4 reduces an acid to a...

1° alcohol

LiAlH4 reduces an ester to a...

1° alcohol

LiAlH4 reduces an acyl chloride to a...

1° alcohol

LiAlH4 reduces an amide to an...

amine

NaBH4 reduces an aldehyde to a...

1° alcohol

NaBH4 reduces a ketone to a...

2° alcohol

LiAlH[OC(CH3)3]3 reduces an acyl chloride to an...

aldehyde

DIBAL-H reduces an ester to an...

aldehyde

CrO3 / Na2Cr2O7 / K2Cr2O7 / KMnO4 oxidizes an aldehyde to a...

carboxylic acid

The reagent ⏤Ag2O, NH4OH⏤ ONLY oxidizes _____.

aldehydes

Ag2O, NH4OH oxidizes aldehydes to...

carboxylic acids

Which reagent converts a carboxylic acid → an acid chloride?

SOCl2

CrO3 / Na2Cr2O7 / K2Cr2O7 / KMnO4 oxidizes a 2° alcohol to a...

ketone

CrO3 / Na2Cr2O7 / K2Cr2O7 / KMnO4 oxidizes a 1° alcohol to a...

carboxylic acid

PCC oxidizes 1° alcohols to...

aldehydes

PCC oxidizes 2° alcohols to...

ketones

Addition of R''MgX to aldehydes forms...

2° alcohols

Addition of R''MgX to ketones forms...

3° alcohols

Addition of NaCN, HCl to an aldehyde or ketone forms a...

cyanohydrin

Addition of a 1° amine to an aldehyde or ketone forms an...

imine

Addition of a 2° amine to an aldehyde or ketone forms an...

enamine

Addition of H2O to an aldehyde or ketone forms a...

gem-diol / hydrate

2 equivalents of CH3OH and H3O+ to an aldehyde or ketone forms an...

acetal

CH3OH, H+ converts a carboxylic acid to an...

ester

SOCl2 converts a carboxylic acid to an...

acid chloride

Addition of R''MgX (2 equivalents) to esters forms...

3° alcohols

Addition of R''MgX (2 equivalents) to acid chlorides forms...

3° alcohols

-Addition of Grignard reagents converts acid chlorides AND esters to 3° alcohols while forming _____ C-C bonds.

-The Grignard reagent adds to the carbonyl carbon _____ during this reaction.

-First, as part of a nucleophilic acyl substitution to form a ketone intermediate.

two ; twice

An acid chloride + carboxylate forms an...

anhydride

When dicarboxylic acid reacts with 𝝙, a _____ forms.

cyclic anhydride

When acid chloride + H2O react with pyridine, a _____ forms.

carboxylic acid

When anhydride + H2O react with each other, what products form?

TWO carboxylic acids

When acid chloride reacts with CH3OH and pyridine, what product forms?

ester

When an anhydride reacts with an alcohol, what products form?

ester AND carboxylic acid

CH3OH, H2SO4 converts a carboxylic acid into an _____ and _____.

This reaction is known as...

-ester and water

-Fisher Esterification

Which reagents convert a carboxylic acid into an ester?

CH3OH, H2SO4

1) NH3 2) 𝝙 converts carboxylic acid into an...

amide

NH3 (1 equiv) converts an ester into an...

amide

NH3 (2 equivalents) converts an anhydride into an...

amide + carboxylate

NH3 (2 equivalents) converts an acid chloride into an...

amide + salt (ammonium chloride)

NH3 (1 equivalent) converts carboxylic acid into a...

carboxylate

H3O+ (hydrolysis) converts a lactone into a _____ and a cyclic acetal into a _____.

-dicarboxylic acid

-diol

1) LiAlH4 2) H2O reduces a nitrile to a...

1° amine

1) DIBAL-H 2) H2O reduces a nitrile to an...

aldehyde

Which reagent reduces nitrile → aldehyde?

1) DIBAL-H

2) H2O

Which reagent reduces nitrile → 1° amine?

1) LiAlH4

2) H2O

1) R'MgX or R'Li 2) H2O reduces a nitrile to a...

ketone

Which reagent reduces a nitrile → ketone?

1) R'MgX or R'Li

2) H2O

H2O (with acid) converts a nitrile to a...

carboxylic acid

Nitriles are prepared by _____ substitution using unhindered alkyl halides as starting materials.

SN2

When a ketone or aldehyde reacts with a Wittig reagent ylide, an _____ forms.

alkene

1) R2BH 2) H2O converts terminal alkynes to...

aldehydes

1) R2BH 2) H2O converts internal alkynes to...

ketones

CO2, H3O+ converts an organometallic reagent to a...

*Remember it adds a new C-C bond!*

carboxylic acid

NaOH converts an alkyl halide to an...

alcohol

Which reagents are used to cleave alkenes?

1) O3 2) Zn, H2O

OR

1) O3 2) CH3SCH3

Which reagents are used to cleave alkynes?

1) O3 2) H2O

Cleavage of internal alkynes produces...

TWO carboxylic acids

Cleavage of terminal alkynes produces...

a carboxylic acid AND CO2

HCl converts ALL alcohols to an...

alkyl chlorides

HBr converts ALL alcohols to...

alkyl bromides

PBr3 converts CH3OH and 1° and 2° alcohols to...

alkyl bromides

H2SO4 converts an alcohol into an...

alkene

KMnO4 CANNOT oxidize quaternary alkyl groups or 3° alcohols. KMnO4 can oxidize aldehydes, alkyl groups (with at least one carbon), and alkenes to...

carboxylic acids

When a ketone reacts with a diol and TsOH, what product is formed?

cyclic acetal

H3O+, heat converts the cyano group (CN) of a cyanohydrin to a...

carboxylic acid

What starting material and what two reagents are needed to form a Wittig Reagent Ylide?

Starting material: alkyl halide

Reagents: 1) Ph3P 2) BuLi

Which reagents are needed to convert an alkyne into a ketone?

H2O, H2SO4, HgSO4

Li, NH3 reduces an alkyne to a...

TRANS alkene