Reactions Overview Flashcards
COMBUSTION OF AN ALKANE
- …Is when you are reacting ____ with ____*
- to produce ____*
Is when you are reacting SOMETHING
with O2
to produce CO2, H2O and HEAT
SYNTHESIS OF AN ALKANE FROM AN ALKENE
- …Is when you are reacting ____ with ____*
- to produce ____*
…Is when you are reacting an ALKENE
with H2 IN THE PRESENCE OF A METAL CATALYST
to produce AN ALKANE
(H2/Pd)
OXIDATION OF AN ALCOHOL
- …Is when you are reacting ____ with ____*
- to produce ____*
…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*
REDUCTION SYNTHESIS OF AN ALCOHOL
- …Is when you are reacting ____ with ____*
- to produce ____*
…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
THE PINACOL REARRANGEMENT
- …Is when you are reacting ____ with ____*
- to produce ____*
Is when you are reacting A VIC-DIOL
with HOT ACID
to produce a KETONE or an ALDEHYDE
PROTECTION OF ALCOHOLS (FROM OXIDATION)
- …Is when you are reacting ____ with ____*
- to produce ____*
- *What will RESTORE the ROH?**
…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
ALCOHOL REACTION WITH SOCl2 AND PBr3
- Is when you are reacting ____ with ____*
- to produce ____*
Is when you are reacting an ALCOHOL (ROH)
with SOCl2 or PBr3
to produce R-Cl or R-Br
FORMATION OF TOSYLATES / MESYLATES
- Is when you are reacting ____ with ____*
- to produce ____*
- **WHY WOULD WE WANT TO USE A TOSYLATE OR MESYLATE?***
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
DEHYDRATION OF AN ALCOHOL, A.K.A.
SYNTHESIS OF AN ALKENE
- Is when you are reacting ____ with ____*
- to produce ____*
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*
GRIGNARD SYNTHESIS
- Is when you are reacting ____ with ____*
- to produce ____*
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
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 ______ _____
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
DECARBOXYLATION OF A β-KETO CARBOXYLIC ACID
- …Is when you are reacting ____ with ____*
- to produce ____*
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)
HALOGENATION OF AN ALDEHYDE OR KETONE
- …Is when you are reacting ____ with ____*
- to form an ____ intermediate, and then reacting THAT intermediate with ___ to form ____*
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
REDUCTION SYSTHESIS OF AMINES
- …Is when you are reacting ____ (2 options) with ____*
- to produce____*
- Is when you are reacting NITRO OR NITRILE GROUPS*
- with* REDUCING AGENTS (LiAlH<span><em>4</em></span> > NaBH4)
- to produce PRIMARY AMINES*
ACETOACETIC ESTER SYNTHESIS
- …Is when you are reacting ____ with a ____*
- to form an ____ intermediate, and then reacting THAT intermediate with ___ to form a ____*
- 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
PINACOL REARRANGEMENT
- Is when you are _________ing a ____*
- to produce a ____*
- via a ___shift*
Is when you are PROTONATING
a VIC DIOL (1,2-diol)
to produce a CARBONYL
via a METHYL SHIFT
ALDOL CONDENSATION
- Is when you are reacting a ____*
- with an ______ or _____, which then attacks*
- _________*
- to produce an _______*
- Is when you are reacting a* BASE, (-OR)
- with* an ALDEHYDE OR KETONE
- which then attacks* ANOTHER (!) ALDEHYDE OR KETONE
- to produce an* ALDOL
“SAPONIFICATION” (HYDROLYSIS OF AN ESTER)
- Is when you are reacting ____ with a ____*
- to form an ____ and a _____ ____ ____*
- Is when you are reacting an* ESTER
- with a* HYDROXIDE ION (NaOH)
- to form an ALCOHOL*
- and a* CARBOXYLIC ACID SALT (Na+)
TRANSESTERIFICATION
- Is when you are reacting a/n _____ with a/n _____,*
- producing a _______ _____*
- Is when you are reacting* AN EXISTING ESTER
- with an* ALCOHOL,
- producing a* DIFFERENT ESTER
GABRIEL SYNTHESIS
Is when you are reacting a ______ ___ with a/n _____ ______, producing a _____ _____
Is an UPGRADE over ALKYL AMIDE SYNTHESIS because?
- 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)*
