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Flashcards in Reactions Overview Deck (20)
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1
Q

COMBUSTION OF AN ALKANE

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

Is when you are reacting SOMETHING

with O2

to produce CO2, H2O and HEAT

2
Q

SYNTHESIS OF AN ALKANE FROM AN ALKENE

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

…Is when you are reacting an ALKENE

with H2 IN THE PRESENCE OF A METAL CATALYST

to produce AN ALKANE

(H2/Pd)

3
Q

OXIDATION OF AN ALCOHOL

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

…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*
4
Q

REDUCTION SYNTHESIS OF AN ALCOHOL

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

…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

5
Q

THE PINACOL REARRANGEMENT

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

Is when you are reacting A VIC-DIOL

with HOT ACID

to produce a KETONE or an ALDEHYDE

6
Q

PROTECTION OF ALCOHOLS (FROM OXIDATION)

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

…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
7
Q

ALCOHOL REACTION WITH SOCl2 AND PBr3

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

Is when you are reacting an ALCOHOL (ROH)

with SOCl2 or PBr3

to produce R-Cl or R-Br

8
Q

FORMATION OF TOSYLATES / MESYLATES

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

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

9
Q

DEHYDRATION OF AN ALCOHOL, A.K.A.

SYNTHESIS OF AN ALKENE

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

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*
10
Q

GRIGNARD SYNTHESIS

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

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

11
Q

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 ______ _____
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
12
Q

DECARBOXYLATION OF A β-KETO CARBOXYLIC ACID

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

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)

13
Q

HALOGENATION OF AN ALDEHYDE OR KETONE

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

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
14
Q

REDUCTION SYSTHESIS OF AMINES

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

A
  • Is when you are reacting NITRO OR NITRILE GROUPS*
  • with* REDUCING AGENTS (LiAlH<span><em>4</em></span> > NaBH4)
  • to produce PRIMARY AMINES*
15
Q

ACETOACETIC ESTER SYNTHESIS

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

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

16
Q

PINACOL REARRANGEMENT

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

Is when you are PROTONATING

a VIC DIOL (1,2-diol)

to produce a CARBONYL

via a METHYL SHIFT

17
Q

ALDOL CONDENSATION

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

A
  • Is when you are reacting a* BASE, (-OR)
  • with* an ALDEHYDE OR KETONE
  • which then attacks* ANOTHER (!) ALDEHYDE OR KETONE
  • to produce an* ALDOL
18
Q

“SAPONIFICATION” (HYDROLYSIS OF AN ESTER)

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

A
  • Is when you are reacting an* ESTER
  • with a* HYDROXIDE ION (NaOH)
  • to form an ALCOHOL*
  • and a* CARBOXYLIC ACID SALT (Na+)
19
Q

TRANSESTERIFICATION

  • Is when you are reacting a/n _____ with a/n _____,*
  • producing a _______ _____*
A
  • Is when you are reacting* AN EXISTING ESTER
  • with an* ALCOHOL,
  • producing a* DIFFERENT ESTER
20
Q

GABRIEL SYNTHESIS

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

Is an UPGRADE over ALKYL AMIDE SYNTHESIS because?

A
  • 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)*