Dienes alder reactions

cyclohexane

Conjugated diene react with alkene to yield a substituted ____

2 new carbon-carbon

Dields alder reaction formes ______ bonds

Diels alder reaction

Conjugated diene react with alkene to yield a substituted cyclohexane

Pericyclic process

The reaction takes place in a single step (a concerted process) involving a ring of e- moving around in a closed loop through a cyclic transition state

cyclohexene

s-cis + ethene results in ____

EDG

e- donating group

EDG

A ____ on diene makes the reaction faster

EWG

e- withdrawing groups

EWG

A ____ on dienophile makes the reaction faster

EDG

Molecule has an R-group (Induction)

Molecule has LP e- next to in (resonance)

EDG

OMe on a s-cis diene would mean it has good ____

EWG

Molecule has Halogens

Pi-bond with electronegative atom (resonance).

EWG

CF3 on dienophile means it has good ____

negative

The diene double bond connect to the R-group will face induction. Where the double bond carbon attached to the R-group has a partial ____ charge because of induction.

positve

Bottom double bond carbon with no attachments that is probably terminal has partial ___ charge.

2-ring structure

Non-cyclic diene plus a cyclic dienophile makes a cute ____ where they each share a bridge bond

bridged 3D

cyclic diene plus a cyclic dienophile makes an ugly ____ structure where the diene is forced to fold up for the dienophile-diene bonds to be made.

True

s-cis will react because it’s concerted. Both of its ends are able to reach out and grab both ends of dienophile.

s bond

sigma bond in between two double bonds

False

s-trans diene will react in diene alder reaction. It is the more stable structure and more favored. And its one hand is able to grab the dienophile.

cannot

Reaction locked in s-trans state ___ react with dienophile

endo

____ bicycle is preferred when attachments=EWG because the TS will be lower in energy when the EWG interacts with the developing pi bond. ___ lowers energy of transition state by having R’s aligned with bridge

endo

EWG in same direction as bridge

exo

EWG in opposite direction as bridge

Endo

Outside substituent goes same dash/wedge direction as ____. +Enant

Exo

Inside substituent goes same dash/wedge direction as ____. +Enant

towards

Endo will face ___ the diene from its double bond

away

Exo will face ___ the diene from its double bond

diene

e- rich

dienophile

e- poor

conjugated diene

This takes priority over alkene and alkyne addition. This is because of resonance, induction, and the most stable carbocation.

EDG

OMe

EWG

CF3

going to attack there

If that carbon has a CF3 attached to it, the diene is ____

THF

Common solvent for dienophile in Diens-Alder