Orgo 1 Synthesis Reactions

Zaitsev Product

Substituent is on more substituted alkene

Hoffman Product

Substituent is on less substituted alkene

Strong Base, Weak Nucleophile

E2 Reaction Needs

Strong Base, Strong Nucleophile

Sn2 and E2 Needs

Weak Base, Strong Nucleophile

Sn1 and Sn2 needs

Weak Base, Weak Nucleophile

Sn1 and E1 need

Polar Protic Solvents

Solvents with O-H and N-H bonds

Syn & Anti

Hydrohalogenation tends to be

Markonikov

HBr has _ addition

Anti-Markonikov

HBr + ROOR has _ addition

Racemic

Compounds that form with a halogen tend to form _ mixtures

Acid-Catalyzed Hydration

This synthesis adds H & OH across a double bond with Markonikov addition

H3O+ and H2O + Dilute H2SO4

Possible reactants for acid-catalyzed hydration

Oxymercuration-Demercuration

In this synthesis, carbocation rearrangements DO NOT occur

Nucleophile

Oxymercuration Demercuration installs the _ into more substitued side

Anti-Markonikov, OH

Hydroboration-Oxidation does _ addition of an _

Syn

Hydroboration-Oxidation only occurs in _ fashion

H2 and Pt

Catalytic Hydrogenation uses these reactants

alkene, alkane

Catalytic Hydrogenation reduces an _ into a _

syn, meso

Catalytic hydrogenation uses __ fashion and tends to form __ compounds

Anti

Halogenation installs halogens in this fashion

OH & OH

Anti Dihydroxylation installs _ across an alkene

Br2 & H2O

Halohydrins are formed when these reagents are used

More

For Halohydrins, the OH goes on the _ substituted carbon

RCO3H & H3O

These reagents are used for anti dihydroxylation

KMnO4, NaOH

Syn Dihydroxylation uses these reagents:

C=O

Oxidative cleavage cleaves an alkene to make two _ bonds

Anti-periplanar

E2 Reactions require the hydrogen and the leaving group to be

Na & NH3

To reduce an alkyne into an alkene, you need these reagents:

Trans

Na and NH3 reduce an alkyne to make a _ alkene

Cis Alkene

H2 and Lindlar’s catalyst make an alkyne into a

NaNH2/NH3 & H2O

To make a terminal alkyne, you need these reagents

No

Can Na & NH3 reduce a terminal alkyne?

H2SO4, H2O, HgSO4

Acid-Catalyzed Hydration of Alkynes uses these reactants

Enol, Ketone

Acid-Catalyzed Hydration of Alkynes will create an __ intermediate and a __ product

Aldehyde

Hydroboration-Oxidation of alkynes makes this functional group

1 eq. X2 & CCl4

Halogenation of an alkyne needs these reagents

Ozonolysis

O3 and H2O form which synthesis?

Carboxylic acid

Ozonolysis of internal alkynes will make two of this functional group:

CO2 and Carboxylic Acid

Ozonolysis of a terminal alkyne makes these products

NaNH2 & RI

Alkylation of Terminal Alkynes occurs with these reagents:

Homolytic bond cleavage

Radical reactions start with this step

Allylic

Which position on an alkene is best for radical mechanisms?

1

Allylic is how many carbons away from the alkene?

3

Radical bromination favors _° radical

Br2, hv

Radical Bromination requires these reagents:

NBS & hv

Allylic bromination uses these reagents:

Hydroxyl on a benzene

Phenol is a

True

T or F: H2 & Pt can be used to reduce a ketone into an OH

False

T or F: NaBH4 and H2O can’t be used to reduce a ketone into an OH

Ketone, Alcohol

LAH and H2O is used to reduce an unsymmetrical _ into a _

Carboxylic acids and Esters

To yield a primary alcohol, you can use LAH on:

R, Reduce

When using RMgBr & H2O tend to install a ___ group and ___ a ketone.

Protecting group

TMS-Cl & Et3N can act as a ___ for an alcohol

TBAF or H3O

TMS can be removed with

TsCl py & NaCl

To replace an alcohol with a halogen, you can use these reagents

Alkyl halides

SOCl2 + Py and PBr3 can convert 1° or 2° alcohols into:

Carboxylic acid

NaCr2O7, H2SO4, and H2O can be used to make 1° alcohols into

PCC & CH2Cl2

To make an aldehyde from a 1° alcohol, you may use

Ether

NaH & RX can make a primary alcohol into a

H2O, ROH

Oxymercuration Demercuration can create ethers if you replace ___ with __.

MCPBA

An epoxide can be prepared from an alkene with this reagent

Br2, NaOH

Epoxides are also made from an alkene when ___ reacts with water and ___.

Terminal alkyne

xs NaNH2 and H2O will transform a carbon with two halogens into a:

NaOH

When an alcohol that is connected to a sp2 hybridized carbon (it is connected to a double bond) is treated with ___, this function group forms a ketone