Here is an post-mortem analysis / "how to" for the MT. The questions are split by the sections. At the start of each section are a few suggestions of what to look for or how to tackle the question type.
Qu1: A
Question about geometry goes back to hybridisation. i
is an alkene so the central C is sp2 , i.e. trigonal
planar, with bond angles of 120o, ii is an
alkane
so the central C is sp3 , i.e. trigonal planar, with
bond angles of 109o, and iii is a cyclobutane
so
the central C is sp3 , but the ring forces the angle down to
almost 90o, therefore giving : i > ii >
iii
Qu2: AB
Since all are CH bonds we should look at the hybridisation of the C
atom.... the greater the s character of the C hybrid used to form the
sigma
bond, the shorter and the stronger that bond will be. Here we have an
alkane
(sp3), an alkene (sp2) and an alkyne (sp)... therefore iii
> ii > i
Qu3: A
Based on the rules for ranking resonance structures, look at the octets
and then charge separation. i has complete octets at C, N
and O and the negative charge on the more electronegative O atom. ii
also has complete octets at C, N and O but now the negative charge on
the
less electronegative C atom. In iii there N has violated the
octet
rule by having 10 electrons around it, which it can't do. Therefore, in
order of importance we have i > ii > iii
Qu4: C
Calculate the formal charges for the N atom = group number - number
of bonds - lone pairs electrons : i = neutral based on 5 - 3 -
2,
ii
= +1 (draw it !) based on 5 - 4 and iii = -1 based on 5 -
2 - 4. Therefore ii > i > iii
Qu5: E
The most stable form (i.e. low energy conformation) of
cyclohexane
is the chair ii. i shows a boat conformation and the iii
the half chair which is quite unstable due to the planar nature for 5
of
the 6 C atoms. this planarity introduces eclipsing interactions and
torsional
strain and is actually the high energy point on the conversion of
cyclohexane
from chair to chair. So we have iii > i > ii
Qu6: D
More branched isomers are more stable due to increased intramolecular
Van der Waals contacts and maximising the number of stronger primary CH
bonds. the more stable the isomer the less exothermic the heat
of
combustion. Therefore ii > iii > i
Qu7: B
Just have to draw them out, no quick way. Constitutional isomers
means different numbers and types of bonds giving different functional
groups and branching patterns.
C3H6O could be propanal, propanone,
cyclopropanol,
1-propen-1-ol, 1-propen-2-ol, 3-propen-1-ol, ethenyl methyl ether,
propylene
oxide, oxacyclobutane (9 isomers).
C3H6 could be propene or cyclopropane (2 isomers).
C6H14 can be a whole bunch of things.... hexane,
2-methylpentane, 3-methylpentane, 2,2-dimethylbutane,
2,3-dimethylbutane
(5 isomers)
So i > iii
>
ii
Qu8: A
The greater the s character in the hybrid then the lower the energy
of that orbital. sp3 is 25%, sp2 is 33% and sp is
50% so therefore in terms of the energies, i > ii
> iii
Qu9: AB
Qu10: C
Qu11: B
Qu12: AC
Qu13: E
Qu14: A
Qu15: CD
Qu16: AE
Water needs to go in at the bottom and out at the top in order to use
gravity to ensure that the condenser is full of water to facilitate
cooling.
Qu17: AD
See above.
Qu18: D
Qu19: A
C3 is attached to 2 x O = -2, 1 x N = -1 and 1 x C = 0 so the
sum = -3, therefore C3 = +3
Qu20: E
C17 is attached to 3 x H = +3 and 1 x O = -1 so the sum = +2,
therefore
C17 = -2
Qu21: D
Since all are CC bonds we need to consider the hybridisation of the
atoms involved and the type of bond. A double bond will be shorter than
a single bond due to the increased bonding interaction. C1-C3
is a single bond sp3 to sp2, C5-C6
is a single bond sp3 to sp3, C6-C7
is a single bond sp3 to sp2, C7-C8
is a double bond sp2 to sp2 C11-C12
is sp2 to sp2 (benzene so between C-C and C=C in
character). Therefore C7-C8 will be the shortest.
Qu22: C
The proximity of the N and C=O system gives the amide group.
Qu23: C
The C-O-C system (no C=O there) implies an ether.
Qu24: C
Count the rings and the p bonds to get 2
rings plus 5 p bonds = 7
Qu25: C
O2 is sp2, because it is involved in the double bond
(1 attached group, 2 lone pairs). N4 is sp2, because
the lone pair is involved in resonance with the C=O double bond (it is
an amide). C5 is sp3 (4 attached groups, 2 C and the
2 undrawn H to assume). N9 is sp2, because the lone
pair
is involved in resonance with the C=C double bond and C11 is sp2
(3 attached groups all C). Most likely you overlooked the effect
of resonance and the requirement to put the lone pair in a p orbital
for
this.
Qu26: C
The diagram shows a Newman projection of cyclohexane in the chair
conformation.
Note that the two -CH2- groups drawn are one up and one down, and that
the sides are in a staggered conformation.
Qu27: D
The methyl group is on a bond in the plane of the ring (equatorial)
while the chlorine is on a bond perpendicular to that plane (axial).
Qu28: B
Isomers that have different functional groups or branching are
constitutional
isomers.
Qu29: CD
To be conformational isomers of methylcyclohexane they need that name.
A
is a cyclohexene system, B is a cyclopentane, C is
a
boat conformation of methylcyclohexane, D is a chair
conformation
of methylcyclohexane and E is the half chair conformation of
just
cyclohexane.
Qu30: B
A is ring strain, B is torsional strain, C
is angle strain, D and E are both steric interactions.
Qu31: D
First draw it out. To be the most stable conformation it needs
to be staggered with the large t-butyl group away from the methyl
group.
B
and E are both eclipsed. A and C are both
staggered
but with the t-butyl group gauche to methyl groups so that leaves
D
where the t-butyl is as far away from the methyl group as possible in
an
anti position.
Qu32: C
An alcohol, -OH has priority low number gives C3, so it's an "-3-ol"
with an alkene that is E (i.e. groups opposite across the C=C).
7 carbon chain so a "hepten-3-ol"
Qu33: B
A ketone, C=O that has priority so it's an "-one". With the C=O at
C1, the lowest number for the methyl groups is C3, two of them so
3,3-dimethyl.
Qu34: B
An ether. Two different groups attached. The benzyl on the left and
a phenyl on the right.
Qu35: B
Complex substituents in an alkane... locate longest chain, here C10,
identify substituents, number based on first point of difference (i.e.
4,4- groups rather than just a 4- group). The complex substituent has a
C2 chain (so ethyl) with a methyl group at C1 so 1-methylethyl located
at C7 on the main chain.... Remember to alphabetise....
Qu36: E
Use the descriptors and look at the -OH group.... A is Z but
has no R or S and the -OH is at C3. B and C are E but
have
no R or S nor the -OH. D is (2Z,5R) and E is (2Z,5S).
Qu37: D
An ester based on benzene narrows it to D or E but E
is a methyl ester.
Qu38: A
Use the descriptors.... first the N,N- means we have two methyl groups
both on the N atom, so C must be wrong. Its also an aldehyde
("-al")
so B and D are out. Down to A and E.
Priority order for groups at the chirality center is N > C=O >
ethyl >
H. A is S, E is R.
Qu39: C
Did you look at bicyclics ? Bicyclic means two fused rings. [2.2.1]
means that there are 2C, 2C and 1C in the links between the shared C
atoms.
This gets rid of E. We number from one of the shared C atoms
via
the longest link first so as to give the alkene the lowest number.