PEC140 Study Block 11 & 12

Additional Study Questions for Organic Comounds

1! "rite condensed formulae and line #ond structures for t$e fi%e structural isomers
of C
&
'
14
! (ame eac$ isomer using t$e )*PAC guidelines for naming organic
comounds!
2! E+lain ,$y alkanes ,it$ u to 4 car#on atoms e+ist as gases- alkanes ,it$ C. /
C10 e+ist as li1uids and alkanes ,it$ C123 e+ist as solids!
4! 5$e follo,ing alkanes all $a%e t$e molecular formula C
.
'
12
- e+lain t$e trend in
#oiling oints!
4!
E+lain ,$y li1uid alkanes are not misci#le ,it$ ,ater!
.! 5$e #oiling oint of et$ane is /26
o
C and t$e #oiling oint for c$loroet$ane is
12
o
C- can you account for t$is difference #et,een t$e t,o comounds!
&! "$y are lo, molecular ,eig$t alco$ols like met$anol and et$anol solu#le in
,ater7
0! E+lain ,$y t$ere is an increase in t$e #oiling oints of straig$t c$ain ali$atic
alco$ols ,it$ increasing lengt$ of t$e car#on c$ain!
2! Eryt$ronolide B is t$e #iological recursor to t$e anti#iotic eryt$romycin 8structure
#elo,9! Assign t$e alco$ols as rimary- secondary or tertiary! Circle and name t$e
ot$er functional grous in eryt$onolide B!
C'
4
C'
2
C'
2
C'
2
C'
4
C '
4
C'
C '
4
C'
2
C'
4
C C'
4
C'
4
C '
4
C'
4
Pentane
BP : 4&
o
C
2;met$yl#utane
BP : 22
o
C
2-2;dimet$ylroane
BP : 6
o
C
O
O
O'
O'
O' O
O'
PEC140 Study Block 11 & 12
Additional Study Questions for Organic Comounds
6! <ra, structures for t$e follo,ing alco$ols and assign t$em as rimary- secondary
or tertiary!
Alcohol Structure Classification
4;et$yl;4;$e+anol
4;met$yl#utanol
10! =et$ylamine is %ery solu#le in ,ater> e+lain $o, t$is is ossi#le and dra, a
diagram to illustrate!
11! 5$e follo,ing organic comounds eac$ contain an amine functional grou!
Classify t$e amines ictured as rimary- secondary or tertiary!
Circle and name t$e ot$er functional grous t$at you recognise!
12! Et$anol and et$anoic acid 8acetic acid9 #ot$ $a%e 2 car#on atoms! 5$e #oiling
oint of et$anol is 02
o
C and t$e #oiling oint for et$anoic acid is 112
o
C- account for
t$e difference in #oiling oint #et,een t$e t,o comounds!
(
'
?cycloentamine@
Central ner%ous system stimulant
(
O
O
O
O
Cocaine
O
(
5amo+ifen
Breast cancer treatment
PEC140 Study Block 11 & 12
Additional Study Questions for Organic Comounds
14! Circle and name t$e functional grous in t$e rostaglandin E
1
molecule- ,$ic$ is
s$o,n #elo,! Classify t$e alco$ol grous as rimary- secondary or tertiary!
14! 5$e follo,ing 1uestions aly to t$e structure of $ydrocortisone ictured #elo,!
Classify t$e alco$ols as rimary- secondary or tertiary! Circle and name t$e ot$er
functional grous!
1.! "rite )*PAC names for t$e follo,ing structures!
O'
O
O
C'
4
C':C'C'C':C'C'C'
4
C'
4
C'
4
O'
O
O
'
('
2
O
O
O
O'
O'
'ydrocortisone
O'
O
O '
O '
O
Prostoglandin E
1
PEC140 Study Block 11 & 12
Additional Study Questions for Organic Comounds
O
)
Br
Br
1&! <ra, structures for t$e follo,ing comounds!
4;et$yl;4;met$yl$etane 4;c$loroentan;2;one
2;#romo;1-4;entadiene 4;c$loro#utyne
4;et$yl;2-4;dimet$yl$e+ane 2;met$ylentan;2;ol
4;et$yl;2-2;dimet$yl$et;4;ene 4;met$yl#utanal
2-.-.;trimet$yl$et;4;yne Proyl acetate
2-&;dimet$yloct;4;yne 2;#romo$etanal
10! "$ic$ of t$e follo,ing alkenes could $a%e a geometric isomer7
Cl
'
4
C '
' O '
' '
C'
2
C'
4
'
4
C
' C'
4
' Cl
Cl C'
4
C'
2
C'
4
PEC140 Study Block 11 & 12
Additional Study Questions for Organic Comounds
12! 5$e e1uations s$o,n #elo, are incomlete! 5$e missing information is t$e
structure of t$e organic roduct- t$e starting organic comound or t$e reagent re1uired
for t$e reaction! Add t$e missing information!
Br
Br

O'
A=nO
4
'
3
O'
O
3
C'
4
C'
2
C'
2
O'
'
3
3
'
2
O
O'
O
A=nO
4
'
3
A=nO
4
'
3