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3. (a) (i) propyl "ethanoate (1)
not &ro&anyl
wron reaent or no reaent scores *ero
n incom&lete reaent s#ch as silver nitrate for ollens, or
&otassi#m dichromate loses the reaent mar+, #t can et
oth oservation mar+s
&enalise oservations which -#st say colo#r chane occ#rs
or only state startin colo#r
(ii) Reaent& NaHCO3(1)
Oservation withC& no reaction (1)
Oservation with D& e$$ere#cence (1) 4
for Cand D NO ollens
.e#t an identi$ied
(hydroen)
carbonate
acidi$ied
/2Cr
2O
0
acidi$ied
/MnO4
correct
"etal
or #tated
indicator
Cl
Ob#eration
ith C
no reaction oe# reen oe#
colourle##
no
reaction
no chane no reaction
ob#eration
ith D
bubble# or
CO2
no chane no chane bubble# or
H2
red or correct
colour
pH 3 56,
("i#ty)
$u"e#
(b) (i) Reaent& pentan-2-one (1)
or 2&entanone
#t not &ent2one or &entyl
(ii) Reaent& .ollen7# or 8ehlin7# (1)
Oservation with E& no reaction (1)
Oservation with F& #iler "irror or red ppt (1) 4
$or Eand F
.e#t .ollen# 8ehlin# or
9enedict#
iodo$or" or
2:NaOH
acidi$ied
/2Cr
2O
0
*chi$$7#
ob#eration ith E no reaction no reaction yello (ppt) no chane no reaction
ob#eration ith F #iler or "irror
or rey or ppt
red or ppt
not red #olution
no reaction oe# reen oe# pin;
(c)
C H C H C C H O
C H
H
3
3
2
(1) 1
m#st e aldehyde. llow C2H
/for CH
0CH
2otherwise this is the
only answer
[9]
Mill Hill High School 3
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Mill Hill High School 4
8/14/2019 4.4, 4.5 exam questions ms.rtf
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4. (a) (i) B& propanoyl chloride (or con#eu#t a# (1) 1
(iii)
(1) 1
(the "ini"u" nece##ary $or the "ar; i# CO and CN #hon)
(i)(CH3CH2CO)2O + H2O 2CH3CH2COOH (1) 1
allo C2H?66
(b) (i) "ethanol (1)
"ethyl propanoate (or con#e
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(c) (i)
( 1 ) ( 1 )
( 1 )( 1 )
C H C H C HC H C H C HC H C H C H C H C H C H
O H O H H
3 33 3 32 2 22
2
+
+
+
H
32 2C H C H C H C H
(ii) to H on carbon in double bond (1)
(iii)
C H C H
H H
C H
C C
H
H
C C
3 33
C H 3
o r( 1 )
ci# but-2-ene (1)tran# but-2-ene 0[14]
6. (a) Reaents Na9H4(1)
y&e of reaction reduction (1) 2
(b) (i) Reaents(s) /2Cr
2O
0(1)H
2*O
4(1)
Conditions re$lux (1)
(ii) CH3CH
2CH
2OH + 2@OA CH
3CH
2COOH + H
2O (1) 4
(c) Reaents HCN or NaCN:H+(1)
Name of mechanism nucleophilic addition (1) 2
(d) (i) "irror i"ae# (1)
(ii) plane polari=ed liht (1)
rotated in oppo#ite direction# (1) 3
(e) (i) *tructure
C H C H C
O C H C H C H
3 2
2 2 3
O
( 1 )
Na"e propyl propanoate (1)
(ii)O C H C H2 3
O
( 1 )H C
3
($) CH3CH
2CO or C
3H
5O + 4 O
2
(1)3 CO
2+ 3H
2O (1) 2
[16]
Mill Hill High School 6
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7. (a) (i) correct raphical $or"ula $or tertiary alcohol
allo CH3not C
2H
(1)
2-"ethylbutan-2-ol : 2-hydroxy-2-"ethylbutane : 2-"ethyl-
2-hydroxybutane aard na"e "ar; een i$ it $ollo#
incorrect $or"ula (1) 2
(ii) raphical $or"ula o$ pent-1-ene (1)
raphical $or"ula o$ pent-2-ene (1) 2
accept eo"etrical i#o"er# o$ pent-2-ene i$ clearly #hon to be di$$erent
(iii) dehydration : eli"ination (1) 1
(i) no H ato"# on C ato" next to COH : three "ethyl roup# on C (1) 1
(b) (i) ethanenitrile : ethanonitrile : "ethyl cyanide :
cyano"ethane : acetonitrile (1) 1
(ii) any hydroly#i# (1) 1
(iii) CH3COCl + CH3NH2 B CH3CONHCH3 + HCl
$or correct $or"ula o$ "ethyla"ine : HCl product (1)
oerall correct (1) 2[10]
8. (a) Na9H4(1) 1
(b) nucleophilic addition (1)
O
H
O &
& C N
C N
+
( 1 )
( 1 )
( 1 )
( 1 )
(1)
(c) (i) hexanedioic acid (1)
(ii) C5H
1%O C
5H
1%O
4
Mr , (1) Mr 145 (1)
264% ,
4%62
D 145 36 (1) 4
[10]
9. (a) (i) ethyl ethanoate
H
C
H
H
H
C
O
O
H
C
H
H
C
H(1) 2
(ii) e#teri$ication : conden#ation : addition - eli"ination (1) 1
Mill Hill High School 7
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(b) (i) a
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10. (a) (i) n appropriate al;eneE CH3CH
2CHCH
2or (CH
3)2CCH
21
#o"er 1 1
#o"er 2 1
o#ition i#o"eri#" 1
Mechani#"
electrophilic attac; and electron #hi$t to 9r (nle## H+
u#ed) 1carbocation 1
reaction ith carbocation 1
llow mechanism mar+s for the al+ene CH0CHCHCH
0
llow one mar+ if mechanism for minor &rod#ct iven
(ii) n appropriate carbonylE CH3CH
2CHO 1
Mechani#" nucleophilic attac; and electron #hi$t to O 1
anion inter"ediate 1
reaction ith anion 1
llow mechanism mar+s for the caronyl (CH3)
2CO
#o"er 1 1#o"er 2 1
Optical i#o"eri#" 1
N3 somer str#ct#res m#st e tetrahedral
N3 5enalise 6stic+ str#ct#res once in &art (a)
(b) Io are chare on carbonyl carbon ato" due to bondin to O and Cl 1
Nucleophile# hae electron pair# hich can be donated 1
J
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