Unit 4 Questions Flashcards
What are stereoisomers?
Isomers with the same structural formula but different orientations in space
What are two molecules in mirror image called?
Enantiomers
What are enantiomers?
Two molecules in mirror image
What is a chiral molecule?
A molecule that cannot superimpose
What does “optically active” mean?
They rotate the plane of polarised light
What is a racemic mixture?
An equimolar mixture of enantiomers that is optically inactive
Give three pieces of evidence against Kekule’s structure of benzene
- Benzene doesn’t decolourise bromine, therefore has no pi-bonds
- X-ray spectroscopy shows equal bond lengths, which means there can’t be a mixture of singles and doubles
- Hydrogenating cyclohexene to cyclohexane should release 360 kJmol-1 but we only get 208, so benzene is more stable
What is resonance energy?
The difference between the experimental delta H reaction for benzene and the delta A reaction according to Kekule’s structure.
Why is benzene more stable than Kekule’s structure?
Because of the electron delocalisation
Give a detailed explanation of the structure of benzene
A planar ring of carbon atoms bonded to one another and to their hydrogens by sigma (sp2) bonds. Each carbon has one unused p orbital with one electron which sit perpendicular to the plane of the ring with one lobe above and one below. Each p-orbital overlaps sideways with two neighbouring orbitals to form a single pi-bond that extends as a ring of charge above and below the plane.
A diagram would probably be good.
What kind of molecules does benzene attract?
Electrophiles because of the great electron density
What do the characteristic reactions of benzene all involve and why?
They all involve substitution because the delocalised ring of electrons makes benzene incredibly stable. Addition would destroy the ring, requiring more energy than it would take to break a C=C bond.
Nitration of benzene. Name the reagents, conditions, and type of reaction.
What happens if the temperature is too high?
Describe/draw the mechanism
Reagents: concentrated sulphuric acid (H2SO4) and concentrated HNO3
Conditions: reflux, 55 degrees C
If the temperature goes above 55, further substitution makes dinitrobenzene.
For the rest see diagram A
What are the two methods of halogenating benzene?
By electrophilic substitution or by free radical addition
Halogenating of benzene by free radical addition: conditions and skeletal equation diagram
UV light at a warm temperature
For the reaction see diagram B
Halogenation of benzene via electrophilic substitution: conditions and skeletal mechanism
Room temperature and a halogen carrier (Friedel-Crafts catalyst)
For reaction see diagram C
Alkylation of benzene: reagents and skeletal mechanism
The alkyl group must be within a halogenoalkane and needs a Friedel-Crafts catalyst
For mechanism see diagram D
Why does hydrolysis of benzene not work under normal conditions when the halogen is attached directly to the ring? What conditions does it need?
The C-Cl bond is too strong in chlorobenzene due to the delocalisation of the pi electron cloud of the ring with the p-orbital electrons (or lone pairs) of the chlorine atom. Furthermore, benzene is already electron rich and therefore not susceptible to nucleophilic attack.
Hydrolysis needs extreme conditions such as 200atm, 473K.
Forming alcohols from halogenoalkanes: reagents, conditions, reaction type.
Give the mechanism (displayed)
What kinds of alcohols does this not work well for and why?
Reagents: Aqueous NaOH solution
Conditions: warm, reflux
Type: nucleophilic substitution
Doesn’t work well for aromatic halides with the halide directly on the ring, as the C-Cl bond is less polar/stronger and therefore less susceptible to nucleophilic substitution
For the mechanism see diagram E
Forming alcohols from carbonyl compounds: give the two reducing agents used and their respective conditions and uses
NaBH4 aqueous at room temperature. Cannot directly reduce carboxylic acid to primary alcohol
LiAlH4 in dry ether at 0 degrees. Used when NaBH4 cannot be.
Formation of alcohols from alkenes: reagents, conditions, and reaction type. The mechanism’s pretty easy so I won’t ask for that.
Add water. Needs phosphoric (V) acid (H3PO4) as a catalyst.
350 degrees, 60 atm
Hydration reaction
Name the three types of compounds from which we can make alcohols
- Alkenes
- Halogenoalkanes
- Carbonyl compounds
Show the oxidisation process of primary alcohols with half ionic equations
See diagram F
What is produced by oxidising each type of alcohol?
Primary —> aldehyde —> carboxylic acid (reflux and excess oxidising agent)
Secondary —> ketone
Tertiary alcohols cannot be oxidised as there are no hydrogens on the hydroxy-bearing carbon