Organic Chemistry Reactions and Reagents: Alcohols, Carbonyls, and Derivatives

What reagent converts a 1° alcohol to an aldehyde?

PCC or DMP

What reagent converts a 1° alcohol to a carboxylic acid?

Na2Cr2O7 / H2SO4 / H2O

What reagent converts a 2° alcohol to a ketone?

PCC, DMP, or Na2Cr2O7

What does alkene ozonolysis yield?

Aldehyde / ketone (O3, DMS)

What reagents convert a terminal alkyne to a ketone?

H2SO4, HgSO4, H2O

What reagents convert a terminal alkyne to an aldehyde?

1) R2BH 2) H2O2/NaOH

What is formed when a carbonyl reacts with H2O?

Geminal diol

What is formed when a carbonyl reacts with ROH and acid?

Acetal

What reagent converts an acetal back to a carbonyl?

H3O+

What is formed when a carbonyl reacts with a 1° amine?

Imine

What is formed when a carbonyl reacts with a 2° amine?

Enamine

What reagents are used in the Wolff-Kishner reduction?

NH2NH2, base, heat → alkane

What reagents are used in the Clemmensen reduction?

Zn(Hg)/HCl → alkane

What does NaBH4 reduce?

Aldehydes / ketones

What does LiAlH4 reduce?

All carbonyls

What does Grignard reagent + formaldehyde yield?

1° alcohol

What does Grignard reagent + aldehyde yield?

2° alcohol

What does Grignard reagent + ketone yield?

3° alcohol

What is formed when cyanide reacts with a carbonyl?

Cyanohydrin

What does the Wittig reaction do?

C=O → C=C

What does Baeyer-Villiger oxidation convert?

Ketone → ester

What reagent converts an acid to an acid chloride?

SOCl2

What is formed when an acid reacts with an alcohol?

Ester, H+

What is formed when an acid chloride reacts with ROH?

Ester

What is formed when an acid chloride reacts with NH3?

Amide

What is the product of ester hydrolysis?

Acid + alcohol

What does ester + LAH yield?

Two alcohols

What does amide + LAH yield?

Amine

What converts nitrile to acid?

H3O+, heat

What does nitrile + LAH yield?

Amine

What is the reactivity order of acid derivatives?

Acid chloride > anhydride > ester > amide