part 1 year 2 how do we make Flashcards

1
Q

what does borazine cosist of

A

B and N cyclic skeleton

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
2
Q

how do u make a borazine with Ph on the B and 1Me on the N

A

u need

3Me2NH2 + 3 BPhCl –> the structure

u also need to remove the 6HCl when u make it

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
3
Q

sp2 C building block makes what

A

cage: fullerenes

2D sheet: graphite

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
4
Q

an sp3 C building block makes what

A

cage: P4 aka white phosphorus
2D sheet: black phosphorus, P.infinity

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
5
Q

describe Pinfinity aka black phosphorus

A

u have a cyclohexane type thing but with P

and u have bonds equitorially to other P’s and lone pairs axially

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
6
Q
A
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
7
Q
A
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
8
Q

huckels rule

A

flat // planar molecule
conjugated double bonds
4n+2 pi electrons
cyclic

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
9
Q

a neutral B with 3 bonds is what hybridisation

A

its sp2

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
10
Q

when u have an O and B adjacent to one another,, why would they both be sp2 hybridised even if they have single bonds

A

bc back donation can occur
the lone pair from O can gi into the empty B orbital giving them both sp2.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
11
Q

how can we say that a normal B with 3 bonds is sp2 hybridised

A

bc it has 3 bonds meaning 3 bonding interactions and no lone pairs and an empty p orbital

3 bonds and an empty p orbital is characteristically sp2!!!

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
12
Q

a dative bond is treated like

A

a dative bond is treated the same as a sigma bond

so it still counts as a normal bond

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
13
Q

B with 4 single bonds is

A

sp3 hybridised

bc sp3 = 4 bonding interactions

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
14
Q

B with 2 single bonds and one double bond is

A

sp2
bc still 120 bond angles

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
15
Q

if theres a N with 3 sigma bonds and a lone pair,, why could it not be sp3

A

look for if the lone pair can be conjugated in the molecule,, if it can,, its sp2.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
16
Q

things to look at to see if smt is sp3, sp2, etc

A
  • how many bonds // lone pairs does it have
  • can the lone pairs be put into a empty p orbital // conjugated into the system
  • look at the bond angles
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
17
Q

when u have a ring with double bonds and the substituents are a phenyl,, when ur choosing whether its aromatic or not,, do i inlude the phenyl e- in the equation

A

nopeee

u just use the e- in the ring

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
18
Q

are BN // borazine rings flate

A

yes

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
19
Q

when is something antiaromatic

A

when its planar, conjugated and cyclic but has 4n pi electrons instead of 4n+2 electrons

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
20
Q

when we draw the lowest energy mo of smt that is aromatic with C, N and B atoms in the ring what do we need to think of

A

think of the large energy diagram thing

with the cicles representing the atoms but remmeber that for benzene all the circles are the same size bc they have the same coefficient bc they have the same electronegativity

but when u have N C and B

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
21
Q

KF and cyclophosphazing

A
  • activates P by making is more electropositive and so addition will be geminal
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
22
Q

cyclophosphazine and 4M2eNH

A

only 2 get added to mop up the HCl formed by making a salt

non geminal bc N: goes into P centre which deactivates it.

trans bc of steric and theyre large

u also make a salt with the X and the rest of the amine

2Me2NH2 (+) Cl(-) this is the salt u form

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
23
Q

lets say the question says u have 1:1 ratio of two things what do we need to look for

A

we need to see if we have a compound of N and a compound with another element.

we need to see if the other element is in the same group as B

if it is ur gonna make a ring with the B compound and N.

ur gonna keep one of the substituents on the B molecule that it comes with,, the N is also gona. ahve one of the substituents it comes with

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
24
Q

1 peak in nmr means what

A

there can be multiple of that element,, but theyre in the same environment

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
25
discuss any pi bonding in a compound and draw its most bonding pi molecular orbital
- what hybridisation is seen - any vacent orbitals and lone pairs - how many pi molecular orbitals : usually 6 : 3 bonding ,, 3 antibonding - how many pi electrons - is it aromatic or not - draw the mo and make sure the larger coefficient is on the right atom
26
when u have Al and N. vs N and B,, what ring will be a better lewis acid
- acids accept - Al is larger p orbital than B,, meaning it experiences poorer donation from the N,, meaning its more likely to accept e- from a lewis base. the coeficcinet is also larger for N in the AlN system bc theres more ionic character bc Al is less electronegative than B.
27
if they ask u to react a ring with pyridine or any other amine,, what do we need to do
we need to think of nongeminal sn2 bc the N deactivates the molecule by adding e- to its p orbital. then we need to think of cis and trans by seeing if its a sterically hindering base.
28
how does the R-E-E angle in REER change from C to Pb aka down the group
it decreases from 180 to 90 due to inert pair effect and s electrons not being used in bonding due to their stronger shielding and penetrative properties
29
effect of R group on alkynes
stericallly protects the triple bond // stabilise the triple bond. with smaller R groups, oligimers tend to form where sigma bond is favoured
30
graphite layers
staggered
31
BN layers in graphite
theyre eclipsed due to favourable electrostatic BN interactions
32
isosteres are what
same e- same shape often similar electronic properties
33
differenes of CC and BN
BN is more polar due to electronegativity differences it can also hydrogen bonds bc u have the electronegative N atom.
34
benzne ewith one BN in the ring ,, with 2 large R groups atatched to the B and N,, where does acyl chloide add
it adds to one of the CC bonds
35
salt usually has what in it
it has a halogen in it and an alkali metal , , so if the product said salt look to swe if u have an alkali metsl and a halogen and dont include these in other products
36
when we heat smt that has lost aromaticity,, what dowe expect it to do
to give smt off to regain aromaticity.
37
a cyclic molecule with E ,, E being N , P or As describe the diff in the structures
- longer bond lengths down the group bc weakrr bonds - weaker bonds due to more idffuse orbital leading to insufficient overlap - less pi stabilisation bc electrons are less delocalised and a larger coef on N than As - more diffuse orbital = more reactive down the group due to orbital mismatch and weaker bond
38
whats cool about the lumo of the ring with As
its the lowest in energy meaning its the one that will most likely react with an electrophile. more idfuse orbital and outermost e- are furthst from the nucleus.
38
fomration of a puckered ring means wha t
non planar,, probs 5 member ring,, not 6
39
what change does P with 2 bonds have
it has a posiitive charge bc we took a Cl from it this also means its sp2 hybridised.
40
carbon dnated how many e- to a ring
it donates 1 e- each
41
N donates how many e- to the ring
it donates 2! if its sp2 hybridised.
42
P(+) has what type of p orbital
it has an empty p orbital so it cant donate any e- to the ring system
43
why is smt planar
its planar if its aromatic
44
why is smt puckered and not planar
if its antiaromaticc /// if its not aromatic if the pi e- count doesnt fit huckels rule
45
when ur asked to draw the isoelectric thing with graphite,, what do u need to make sure u do
draw it eclipsed draw it with single bonds only
46
how do u draw the isoelectric version of diamond
just draw chicken feet stacked up N with 4 bonds and bonded to B all times
47
graphite vs the BN version and their physical property differences
BN has more ionic character which reduces its electrical conductivity. interlayer interaction between the slight -N and slight+B results in a more hard BN graphite than just graphite.
48
when u add Br2 to borazine where does it go
one Br goes on every atom. then when u reflux it ends up being on B only.
49
HCl and borazine
Cl on B H on N
50
H2O on borazine
OH on B H on N reflux leaves OH on B
51
borazine with Cl on B and phLi
u get Ph on every B and LiCl as a product
52
essential characteristic of bonding or borazine
- everything is sp2 - lone pair from N so all 6pi electrons come from N. - B is- N is + via resonance but acc partial charges are the opposite of this - draw the 3 bonding MOs for it,, remember the coefficient to be bigger on N.
53
essential bonding characteristics of cyclophosphazines
- N is sp2 - P is sp3 - both contribute 1e- to the pi system so 6pi electrons in total : out of plane pi bonding - without d orbitals the in plane lone pair // e- pair backbond into the PX antibonding orbital. with d orbitals the in plane lone pair backbonds into the d orbital - R group on P dictates how strong pi in plane bonding is (flat d orbitals - clover shape) - theres also out of plane pi bonding : with d orbitals but orientated randomly: 2 bottom mo with node at p or n,, then one without a node, ,the d orbitals just have a bonding interaction on the inner bit)
54
in cyclophosph asll things get added to what
all things get added to the P either nongemical or geminal
55
in cyclophosph u have use of d obitals or not : whats the inplane and out of plane thing
u have d orbitals i nand out of plane u have sigma* aorbitals in and out of plane just depends where the lone pair is either in the pz or pxy orbital on N. and then the d orbitals switch orientation to be flat or 3d (2 diff 3d versions) in in plane sigma* u add to the PN sigma* and the lone pair is in a hybrid in out of plane sigma* is on the p-x bond and the lone pair is in a pz orbital
56
if u have a borazine but with diff elements like BP instead of BN,,, then the p and b are gonna have what hybridisatipn
b and p will both be sp2,, bc its a type of borazineeee bc its isoelectric to borazine,, planar,, 6pi electrons etc etc.
57
in a PB ring thats means to be like borazine,, why are the PB bonds short
bc the P donates its lone pair to the B which results in short BP bonds. the e- are delocalised around the ring and therefore the bond lengs will be between a BP single and double bond
58
if u have a borazine but with slightly diff elements and they ask u to descrbe the bonding what should u do
u should copy borazine hydridisation ,, both things being sp2 ] if u have the same thing with cyclophospazine remember P is sp3 and N is sp2
59
when theres poorer overlap of orbitals between BP compared to BN,, what else is there
theres a reduction in aromaticity in the BP system bc poorer orbital overlap
60
when u have a 4 membered ring and u need to compare it with a 6 member ring what should u do
4 member ring could be antiaromatic if it has 4n electrons the ring will probs be puckered due to this,, to reduce antiaromaticity. the 4 membered ring will therefore be less stable and more reactive as a result of this.
60
why is a BN ring more stable than a BP ring
BN have better overlap as theyre both 2p ,, same size same energy = stronger bonds BP have 2p and 3p,, larger in energy and more diffuse so less overlap. = weaker bonds less of an electronegativity difference so the PB ring is less stable and therefore more reactive
61
MeSH being a nuc to cyclophosphazine, how does it get added
it gets added geminally bc it allows for easy rehydribisation of the TS ,, lowing the Ea for nucleophilic attack using the second SMe
62
6H2o being added to cyclophosphazine,, what do we do
we add these to a P ,, but one will be a carbonyl and one will be an OH