Exam 2 Flashcards
How much more stable are conjugated dienes than isolated dienes?
** Because of resonance!!! **
Conjugated dienes are 27 kJ/mol more stable than isolated dienes
Examples of EWG
Aldehydes, Ketones, Esters, Amides, Carboxylic Acids, Nitriles, Nitros, Sulfones, & Sulfoxides
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/571/905/a_image_thumb.png?1626707749)
Examples of EDG
Alkoxys, Syllyloxys, Aminos, Ester’s oxygen, Amide’s nitrogen, Alkyls
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/574/619/a_image_thumb.png?1626707926)
Diene Reactivity
** Want most stable s-cis conformation **
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/574/836/a_image_thumb.png?1626708303)
Diels-Alder Reaction Stereochemistry
Concerted mechanism = no changes in conformation
** Racemic mixtures because products are not chiral, so products must not have chirality **
Endo Transition State: EWG pointing in towards newly formed pi bond
** Stabilized by overlap between pi bond and p-orbital **
Exo Transition State: EWG pointing away from newly forming pi bond
Pyrrole
Resonance Energy = 22 Kcal/mol
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/575/935/a_image_thumb.png?1626710413)
Imidazole
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/577/023/a_image_thumb.png?1626710454)
Furan
RE = 16 Kcal/mol
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/577/041/a_image_thumb.png?1626710487)
Thiophene
RE = 29 Kcal/mol
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/577/087/a_image_thumb.png?1626710545)
Pyridine
RE = 22 Kcal/mol
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/577/183/a_image_thumb.png?1626710581)
Pyrimidine
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/577/199/a_image_thumb.png?1626710626)
Purine
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/577/256/a_image_thumb.png?1626710660)
Indole
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/577/272/a_image_thumb.png?1626710693)
Benzofuran
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/577/284/a_image_thumb.png?1626710717)
Quinoline
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/577/307/a_image_thumb.png?1626710747)
Benzene
RE = 36 Kcal/mol
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/577/353/a_image_thumb.png?1626710781)
Napthalene
RE = 60 Kcal/mol total, 30 Kcal/mol per ring
** Resonance energy per ring decreases as conjugation increases **
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/577/378/a_image_thumb.png?1626710852)
Anthracene
RE = 84 Kcal/mol total, 28 Kcal/mol per ring
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/577/431/a_image_thumb.png?1626710894)
Phenanthrene
RE = 91 Kcal/mol total, 30 Kcal/mol per ring
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/577/461/a_image_thumb.png?1626710958)
Phenol
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/577/481/a_image_thumb.png?1626711011)
Toluene
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/577/515/a_image_thumb.png?1626711032)
Xylene
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/577/528/a_image_thumb.png?1626711055)
Aniline
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/577/546/a_image_thumb.png?1626711085)
Benzoic Acid
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/577/560/a_image_thumb.png?1626711123)
Styrene
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/577/589/a_image_thumb.png?1626711151)
Anisole
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/577/621/a_image_thumb.png?1626711183)
Cresol
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/577/626/a_image_thumb.png?1626711211)
Aromatic Ring
Common Nomenclature
Name substituents with ortho (o), meta (m), para (p)
![](https://s3.amazonaws.com/brainscape-prod/system/cm/351/577/643/a_image_thumb.png?1626711384)