4.4, 4.5 exam questions ms.rtf

8/14/2019 4.4, 4.5 exam questions ms.rtf

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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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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]



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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



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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

4.4, 4.5 exam questions ms.rtf

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