Reactants- Ochem 2 Exam 1

What are the reactants/reagents for benzene nitration?

HNO₃ + H₂SO₄

What is the product of benzene nitration?

Nitrobenzene (C₆H₅NO₂)

What electrophile is generated in benzene nitration?

NO₂⁺ (nitronium ion)

What are the reactants/reagents for benzene sulfonation?

SO₃ + H₂SO₄

What is the product of benzene sulfonation?

Benzenesulfonic acid (C₆H₅SO₃H)

What are the reactants/reagents for benzene bromination?

Br₂ + FeBr₃

What is the product of benzene bromination?

Bromobenzene

What are the reactants/reagents for benzene chlorination?

Cl₂ + FeCl₃

What is the product of benzene chlorination?

Chlorobenzene

What are the reactants/reagents for Friedel-Crafts alkylation?

R–Cl + AlCl₃

What is the product of Friedel-Crafts alkylation?

Alkylbenzene (benzene with an R group)

What electrophile is generated in Friedel-Crafts alkylation?

A carbocation or carbocation-like electrophile (R⁺)

What are the reactants/reagents for Friedel-Crafts acylation?

RCOCl + AlCl₃

What is the product of Friedel-Crafts acylation?

Aryl ketone (benzene–C(O)R)

What electrophile is generated in Friedel-Crafts acylation?

Acylium ion (RCO⁺)

What are the reagents for a Clemmensen reduction?

Zn(Hg), HCl

What functional group does Clemmensen reduction convert?

Ketone/aldehyde C=O → CH₂

What are the reagents for a Wolff-Kishner reduction?

NH₂NH₂, strong base, heat

What functional group does Wolff-Kishner reduction convert?

Ketone/aldehyde C=O → CH₂

What are the reagents for oxidation of an alkylbenzene to benzoic acid?

KMnO₄, heat, followed by acidic workup

What starting material is required for alkylbenzene oxidation to benzoic acid?

An alkylbenzene with at least one benzylic H

What is the product of alkylbenzene oxidation?

Benzoic acid (Ar–CO₂H)

What are the general reactants for nucleophilic aromatic substitution (NAS)?

An aryl halide + nucleophile

What is the general product of NAS?

The nucleophile replaces the aryl leaving group

What conditions favor NAS?

An electron-deficient aromatic ring, especially with EWG(s) ortho/para to the leaving group

What are the possible leaving groups in NAS?

F, Cl, Br, or I

What is the typical leaving group reactivity order in SNAr?

F > Cl > Br > I

What are the reactants for forming an organolithium reagent?

R–X + 2 Li → R–Li + LiX

What are the reactants/reagents for forming a Grignard reagent?

R–X + Mg, dry ether → R–MgX

What conditions are required to form Grignard/organolithium reagents?

Strictly dry conditions; water/protic compounds must be excluded

What happens when an organometallic reagent reacts with an alcohol?

The organometallic reagent acts as a base and deprotonates the O–H group

What happens when an organometallic reagent reacts with water?

It is protonated and destroyed

What happens when an organometallic reagent reacts with a carboxylic acid?

It is protonated by the acidic O–H and destroyed

What are the reactants for making an alcohol from a carbonyl using a Grignard reagent?

Carbonyl compound + R–MgX, followed by H₃O⁺ workup

What are the reactants for making an alcohol from a carbonyl using an organolithium?

Carbonyl compound + R–Li, followed by H₃O⁺ workup

What product forms when formaldehyde reacts with a Grignard/organolithium reagent?

Primary alcohol

What product forms when an aldehyde reacts with a Grignard/organolithium reagent?

Secondary alcohol

What product forms when a ketone reacts with a Grignard/organolithium reagent?

Tertiary alcohol

What are the reagents for hydrogenation of an aldehyde or ketone?

H₂ + metal catalyst (such as Pt, Pd, or Ni)

What does hydrogenation of an aldehyde produce?

Primary alcohol

What does hydrogenation of a ketone produce?

Secondary alcohol

What are the reagents for reducing an aldehyde/ketone with NaBH₄?

NaBH₄, followed by aqueous workup

What does NaBH₄ reduce?

Aldehydes and ketones → alcohols

What does an aldehyde become with NaBH₄?

Primary alcohol

What does a ketone become with NaBH₄?

Secondary alcohol

What are the reagents for reducing an aldehyde/ketone with LiAlH₄?

LiAlH₄, followed by H₃O⁺ workup

What does LiAlH₄ reduce?

Aldehydes, ketones, carboxylic acids, and esters

What does an aldehyde become with LiAlH₄?

Primary alcohol

What does a ketone become with LiAlH₄?

Secondary alcohol

What does a carboxylic acid become with LiAlH₄?

Primary alcohol

What does an ester become with LiAlH₄?

Two alcohol products

What are the reagents for reducing a carboxylic acid to a primary alcohol?

1. LiAlH₄ 2. H₃O⁺

What is the difference between H₂ and H⁻ in carbonyl reduction?

H₂ adds hydrogen through catalytic hydrogenation; H⁻ is delivered by metal hydrides such as NaBH₄ or LiAlH₄

What are the reactants/reagents for opening ethylene oxide to make a primary alcohol?

Ethylene oxide + nucleophile, followed by acidic workup

What happens when a nucleophile opens an epoxide?

The epoxide ring opens and the carbon bearing the nucleophile becomes bonded to the nucleophile; the other carbon becomes an alcohol after workup

What are the general reactants for ether formation from two primary alcohols?

Two primary alcohols + acid catalyst, with appropriate heating/conditions

What is the product of intermolecular ether formation from primary alcohols?

An ether + water

What is the product of intramolecular ether formation from a suitable diol?

A cyclic ether + water

What is required for intramolecular ether formation?

The molecule must contain an alcohol and another suitable carbon bearing an OH group positioned to form a ring

What are the reagents for forming a vicinal diol with OsO₄?

OsO₄, followed by appropriate oxidative/reductive workup depending on the course conditions

What does OsO₄ do to an alkene?

Converts the alkene into a syn vicinal diol

What is the stereochemical result of OsO₄ oxidation?

Syn addition; the two OH groups end up on the same face

What are the general reactants for ester formation?

An alcohol + carboxylic acid derivative

What are the reactants/reagents for Fischer esterification?

Carboxylic acid + alcohol + acid catalyst

What are the products of Fischer esterification?

Ester + H₂O

What principle drives Fischer esterification toward products?

Le Châtelier's principle

How can Fischer esterification be pushed toward ester formation?

Remove water and/or use excess alcohol

What are the reactants for forming an ester from an alcohol and an acid chloride?

Alcohol + acid chloride

What are the products of alcohol + acid chloride reaction?

Ester + HCl

What are the reactants for forming an ester from an alcohol and an acid anhydride?

Alcohol + acid anhydride

What are the products of alcohol + acid anhydride reaction?

Ester + carboxylic acid