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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]

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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