Reactions Overview

Question 1

COMBUSTION OF AN ALKANE

• …Is when you are reacting ____ with ____*
• to produce ____*

Answer 1

Is when you are reacting SOMETHING

with O₂

to produce CO₂, H₂O and HEAT

Question 2

SYNTHESIS OF AN ALKANE FROM AN ALKENE

• …Is when you are reacting ____ with ____*
• to produce ____*

Answer 2

…Is when you are reacting an ALKENE

with H₂ IN THE PRESENCE OF A METAL CATALYST

to produce AN ALKANE

(H₂/Pd)

Question 3

OXIDATION OF AN ALCOHOL

• …Is when you are reacting ____ with ____*
• to produce ____*

Answer 3

…Is when you are reacting AN ALCOHOL (1° or 2°) with an OXIDIZING AGENT

to produce EITHER KETONES (2°) or ALDEHEDYDES/COOHs (1°)

• OXIDIZING AGENTS:*
• O₃, Cr₂O₇, CrO₄, KMnO₄, Jones, Collins, PCC, PDC*

Question 4

REDUCTION SYNTHESIS OF AN ALCOHOL

• …Is when you are reacting ____ with ____*
• to produce ____*

Answer 4

…Is when you are reacting KETONES, ALDEHYDES, COOHs or ESTERS (PREVIOUSLY OXIDIZED ALCOHOLS)

with REDUCING AGENTS

to produce (reduced) ALCOHOLS

REDUCING AGENTS:

LiAlH_{<strong>4</strong>} (STRONGEST), NaBH₄, H₂/pressure

Question 5

THE PINACOL REARRANGEMENT

• …Is when you are reacting ____ with ____*
• to produce ____*

Answer 5

Is when you are reacting A VIC-DIOL

with HOT ACID

to produce a KETONE or an ALDEHYDE

Question 6

PROTECTION OF ALCOHOLS (FROM OXIDATION)

• …Is when you are reacting ____ with ____*
• to produce ____*
• *What will RESTORE the ROH?**

Answer 6

…Is when you are reacting an ALCOHOL

with TMS or MOM

to produce RO-TMS or RO-MOM

• This protects ROHs from oxidation while still allowing the reaction to occur with OTHER functional groups on the molecule*
• ACIDIFICATION will remove TMS or MOM and restore the ROH

Question 7

ALCOHOL REACTION WITH SOCl₂ AND PBr₃

• Is when you are reacting ____ with ____*
• to produce ____*

Answer 7

Is when you are reacting an ALCOHOL (ROH)

with SOCl₂ or PBr₃

to produce R-Cl or R-Br

Question 8

FORMATION OF TOSYLATES / MESYLATES

• Is when you are reacting ____ with ____*
• to produce ____*
• **WHY WOULD WE WANT TO USE A TOSYLATE OR MESYLATE?***

Answer 8

Is when you are reacting Tosyl-Cl (or Mesyl-Cl)

with an ALCOHOL (ROH)

to produce Tosyl-OR and HCl

Mesylates and Tosylates are desirable because they make very good leaving groups that will react readily with almost any nucleophile

Question 9

DEHYDRATION OF AN ALCOHOL, A.K.A.

SYNTHESIS OF AN ALKENE

• Is when you are reacting ____ with ____*
• to produce ____*

Answer 9

Is when you are reacting an ALCOHOL

with an ACID

to produce WATER, and subsequently an ALKENE

• WATER LEAVES, FORMING CCI*
• ELECTRONS COLLAPSE, FORMING DB*

Question 10

GRIGNARD SYNTHESIS

• Is when you are reacting ____ with ____*
• to produce ____*

Answer 10

Is when you are reacting a CARBONYL ***

with RMgX

to produce an ALCOHOL

WITH AN EXTENSION OF THE CARBON CHAIN!!!!

***YOU CAN ALSO DO THIS REACTION WITH ELECTROPHILIC DB’S SUCH AS:

C=N,** **CYANO** GROUPS, **S=O,** AND **N=O

Question 11

HOFFMAN DEGRADATION

• Is when you are reacting ____ with ____*
• to produce ____*
• THIS RXN _____S THE CARBON CHAIN
• THIS RXN IS IMPORTANT BECAUSE IT ALLOWS YOU TO ADD ___ TO A ______ _____

Answer 11

REACTING A PRIMARY AMIDE

WITH STRONG, BASIC SOLUTIONS OF:

Cl₂ OR Br₂

TO PRODUCE A PRIMARY AMINE

• This reaction SHORTENS the carbon chain
• Rxn is important because it allows you to add an AMIDE to a TERTIARY CARBON

Question 12

DECARBOXYLATION OF A β-KETO CARBOXYLIC ACID

• …Is when you are reacting ____ with ____*
• to produce ____*

Answer 12

Is when you are reacting A β-KETO CARBOXYLIC ACID

with :B (A BASE)

to produce CO₂ + A RESONANCE-STABILIZED CARB_ANION_

(ENOL ⇔KETO TAUTOMERS)

Question 13

HALOGENATION OF AN ALDEHYDE OR KETONE

• …Is when you are reacting ____ with ____*
• to form an ____ intermediate, and then reacting THAT intermediate with ___ to form ____*

Answer 13

Is when you are reacting

AN α-HYDROGEN OF AN ALDEHYDE OR KETONE

• with* A BASE (ex: NaOH)
• to form* an ENOLATE intermediate
• and then reacting THAT with* X_{<span>2</span>} (ex: Br₂)
• to form an α*-HALOGENATED PRODUCT

Question 14

REDUCTION SYSTHESIS OF AMINES

• …Is when you are reacting ____ (2 options) with ____*
• to produce____*

Answer 14

• Is when you are reacting NITRO OR NITRILE GROUPS*
• with* REDUCING AGENTS (LiAlH_{<span><em>4</em></span>} > NaBH₄)
• to produce PRIMARY AMINES*

Question 15

ACETOACETIC ESTER SYNTHESIS

• …Is when you are reacting ____ with a ____*
• to form an ____ intermediate, and then reacting THAT intermediate with ___ to form a ____*

Answer 15

• Is when you are reacting a* β-KETO ESTER with A BASE
• to form a* CARBANION intermediate
• and then reacting THAT intermediate with an* ALKYL HALIDE (RX) to form a KETONE

A base abstracts the acidic alpha hydrogen, leaving a carbanion
The carbanion attacks an alkyl halide (R-X), resulting in addition of the –R group to the alpha carbon
Hot acid during workup causes loss of the entire –COOR group

Question 16

PINACOL REARRANGEMENT

• Is when you are _________ing a ____*
• to produce a ____*
• via a ___shift*

Answer 16

Is when you are PROTONATING

a VIC DIOL (1,2-diol)

to produce a CARBONYL

via a METHYL SHIFT

Question 17

ALDOL CONDENSATION

• Is when you are reacting a ____*
• with an ______ or _____, which then attacks*
• _________*
• to produce an _______*

Answer 17

• Is when you are reacting a* BASE, (-OR)
• with* an ALDEHYDE OR KETONE
• which then attacks* ANOTHER (!) ALDEHYDE OR KETONE
• to produce an* ALDOL

Question 18

“SAPONIFICATION” (HYDROLYSIS OF AN ESTER)

• Is when you are reacting ____ with a ____*
• to form an ____ and a _____ ____ ____*

Answer 18

• Is when you are reacting an* ESTER
• with a* HYDROXIDE ION (NaOH)
• to form an ALCOHOL*
• and a* CARBOXYLIC ACID SALT (Na⁺)

Question 19

TRANSESTERIFICATION

• Is when you are reacting a/n _____ with a/n _____,*
• producing a _______ _____*

Answer 19

• Is when you are reacting* AN EXISTING ESTER
• with an* ALCOHOL,
• producing a* DIFFERENT ESTER

Question 20

GABRIEL SYNTHESIS

Is when you are reacting a ______ ___ with a/n _____ ______, producing a _____ _____

Is an UPGRADE over ALKYL AMIDE SYNTHESIS because?

Answer 20

• Is when you are reacting a* PHTHALIMIDE ION
• with an* ALKYL HALIDE,
• producing a* PRIMARY AMINE
• Is an UPGRADE because it avoids the side products that the you get doing doing Alkyl Amine Synthesis*
• (remember that AAS results in many side products b/c the resultant amine is still a good Nu: and can react AGAIN)*