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    1 . Arra n ge the followin g in decrea sin g order of th eir boilin g poin ts .

    (A) nbu ta n e (B) 2m eth ylbu ta n e

    (C) n -pen ta n e (D) 2 ,2d im eth ylpropa n e

    (i) A > B > C > D

    (ii) B > C > D > A

    (iii) D > C > B > A

    (iv) C > B > D > A

    2 . Arran ge th e ha logen s F2

    , Cl2

    , Br2

    , I2

    , in ord er of th eir in creas ing reactivitywith alkan es.

    (i) I2

    < Br2

    < C l2

    < F2

    (ii) Br2

    < C l2

    < F2

    < I2

    (iii) F2

    < C l2

    < Br2

    < I2

    (iv) Br2

    < I2

    < C l2

    < F2

    3 . Th e in creas ing order of redu ction of alkyl halides with zinc an d dilut e HCl is

    (i) RCl < RI < RBr

    ii) RCl < RBr < RI

    (iii) RI < RBr < RCl

    (iv) RBr < RI < RCl

    I. Multiple Choice Questions (Type-I)

    U nitU nitU nitU nitU nit

    1313HHHHHYDRYDRYDRYDRYDROCOCOCOCOCARBONSARBONSARBONSARBONSARBONSHHHHHYDRYDRYDRYDRYDROCOCOCOCOCARBONSARBONSARBONSARBONSARBONS

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    1 6 2Exemplar Problems, Chemis t ry

    4 . The correct IUPAC n am e of th e following a lkan e is

    (i) 3 ,6 Die thyl 2 methyloctane

    (ii) 5 Isopropyl 3 ethyloctane

    (iii) 3 Ethyl 5 isopropyloctane

    (iv) 3 Isopropyl 6 e thyloctan e

    5 . Th e add ition of HBr to 1-bu tene gives a mixtu re of produ cts A, B an d C

    (A) (B) (C)

    Th e mixtu re cons ists of

    (i) A a nd B a s m a jo r a nd C a s m inor p r oduc t s

    (ii) B a s m a jor, A a nd C a s m inor p r oduc ts

    (iii) B as minor, A and C as major produc ts

    (iv) A a nd B a s m inor a nd C a s m a jo r p r oduc t s

    6 . Wh ich of the following will not sh ow geom etrical isomerism ?

    (i)

    (ii)

    (iii)

    (iv)

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    1 6 3 H ydroca rbons

    7 . Arra n ge the followin g hydrogen h alides in ord er of th eir decreas ing reactivitywith p ropene.

    (i) H Cl > H Br > HI

    (ii) HBr > HI > HCl(iii) HI > HBr > HCl

    (iv) HCl > HI > HBr

    8 . Arra n ge the followin g carba n ions in ord er of th eir decreas ing sta bility.

    (A) H3C C C

    (B) H C C

    (C)

    (i) A > B > C

    (ii) B > A > C

    (iii) C > B > A

    (iv) C > A > B

    9 . Arrange the fol lowing a lkyl hal ides in decreasing order of the ra te of

    elimina tion r eaction with alcoholic KOH.

    (A) (B) CH3CH

    2Br (C) CH

    3CH

    2CH

    2Br

    (i) A > B > C

    (ii) C > B > A

    (iii) B > C > A(iv) A > C > B

    1 0 . Wh ich of th e followin g react ion s of met h an e is incom plete com bu st ion :

    (i) 2CH4

    + O2

    Cu / 523 K/ 100 a tm 2 CH3OH

    (ii) CH4

    + O2 2 3

    Mo O HCHO + H2O

    (iii) CH4

    + O2 C(s ) + 2H

    2O (l)

    (iv) CH4

    + 2 O2 CO

    2(g) + 2H

    2O (l)

    II. Multiple Choice Questions (Type-II)

    In th e fol lowing quest ions two or more opt ions may be c orrect .

    1 1 . Some oxida tion reaction s of meth an e are given b elow. Which of th em is/ are

    cont rolled oxidation react ion s?

    (i) CH4

    (g) + 2 O2

    (g) CO2

    (g) + 2 H2O ( l)

    (ii) CH4

    (g) + O2

    (g) C (s) + 2H2O (l)

    (iii) CH4

    (g) + O2

    (g) 2 3Mo O HCHO + H

    2O

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    1 6 4Exemplar Problems, Chemis t ry

    (iv) 2CH4

    (g) + O2

    (g) Cu / 523 / 100 at m 2CH

    3OH

    1 2 . Which of the following alken es on ozon olysis give a m ixtur e of keton es on ly?

    (i) CH3CH CHCH

    3

    (ii)

    (iii)

    (iv)

    1 3 . Which ar e th e correct IUPAC na m es of th e following compou n d?

    (i) 5 Butyl 4 isopropyldecane

    (ii) 5 Ethyl 4 propyldecane

    (iii) 5 sec-Bu tyl 4 iso-propyldecane(iv) 4(1-meth ylethyl) 5 (1-meth ylpropyl)-decan e

    1 4 . Wh ich ar e th e correct IUPAC na m es of th e following compou n d?

    (i) 5 (2 , 2 Dimethylpropyl)-decane(ii) 4 Butyl 2 ,2 d imethylnonan e

    (iii) 2,2 Dimethyl 4 pentyloctan e

    (iv) 5 neo-Pentyldecane

    1 5 . For an electroph ilic su bst itu tion r eaction, th e presen ce of a h alogen a tom in

    th e be n zene rin g _______.

    (i) deactivates the r ing by indu ctive effect

    (ii) deact iva tes the r ing by resonance

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    1 6 5 H ydroca rbons

    (iii) increases the charge density a t or tho and p ara posi t ion re la t ive to meta

    position by resonan ce

    (iv) directs the incoming e lectrophile to meta posit ion by increasing thecha rge den sity relative to ortho an d pa ra p osition.

    1 6 . In an electrophilic su bs titut ion rea ction of nitroben zen e, the pr esen ce of nitrogrou p ________.

    (i) deactivates th e r ing by indu ctive effect .

    (ii) act ivates th e r ing by indu ctive effect .

    (iii) decreases th e charge dens ity a t or tho and para pos it ion of the r ing

    relative to meta position b y resonan ce.

    (iv) increases the charge dens ity a t meta posi t ion re la t ive to the or tho and

    pa ra pos itions of th e rin g by resona nce.

    1 7 . Wh ich of th e following a re corr ect?

    (i) CH3O

    2CH is m ore stable than CH

    3

    2CH

    (ii) (CH3)2CH is less st able than CH

    3CH

    2

    2CH

    (iii) CH2

    CH2CH is m ore stable tha n CH

    3CH

    2

    2CH

    (iv) CH2 CH is m ore stable than CH

    3

    2CH

    1 8 . Four stru ctu res a re given in option s (i) to (iv). Exam ine th em a nd select th earomatic s tru ctures.

    (i) (ii)

    (iii) (iv)

    1 9 . The m olecu les h avin g dipole mom en t a re __________.

    (i) 2 ,2 -Dim e th ylp r op a n e

    (ii) trans -Pent-2-ene

    (iii) cis -Hex-3-ene

    (iv) 2 , 2 , 3, 3 - Te tr a m e thy lbu ta ne .

    III. Short Answer Type

    2 0 . Why do a lkenes p refer to u n dergo electrophilic ad dition r eaction while aren es

    prefer electrophilic su bst itution reactions ? E xplain.

    2 1 . Alkynes on redu ction with s odiu m in l iqu id amm onia form tra ns a lkenes.Will the bu tene th u s formed on redu ction of 2-bu tyne sh ow the geometr ical

    isomerism?

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    1 6 6Exemplar Problems, Chemis t ry

    2 2 . Rotation a roun d carb on-carbon single bond of etha ne is n ot comp letely free.

    J us t ify the sta tement.

    2 3 . Draw Newman and Sawhorse projections for the eclipsed and staggered

    conforma tions of etha n e. Which of th ese conforma tions is more sta ble and why?

    2 4 . The int ermed iate carbocat ion formed in th e reactions of HI, HBr an d HCl withpropene is the s am e an d th e bond en ergy of HCl, HBr an d HI is 4 30.5 kJ mol

    1,

    363 .7 kJ mol1

    a nd 296 .8 kJ m ol1

    respectively. What will be the order of

    react ivity of th ese h alogen a cids?

    2 5 . Wh at will be the pr odu ct obta ined as a res u lt of th e followin g reaction a n d why?

    2 6 . How will you convert ben zene in to (i) p nitrobromoben zen e(ii) m nitrobrom obenzene

    2 7 . Arra n ge the followin g set of comp ou n ds in th e order of th eir decreas ing relativereactivity with an electroph ile.Give reason .

    2 8 . Despite th eir - I effect, h alogens are o- and p-directing in h aloaren es. Explain .

    2 9 . Wh y does presen ce of a n itro grou p m ak e the b enzene ring less reactive incompa rison to th e un su bsti tuted b enzene r ing. Explain.

    3 0 . Su ggest a rout e for th e prepar ation of nitroben zen e sta rting from a cetylen e?

    3 1 . Predict th e m ajor produ ct (s) of th e following reactions an d explain th eir form ation.

    H3CCH CH

    2 r2

    (Ph -CO-O)

    HB

    H3CCH CH

    2

    HB r

    3 2 . Nu cleophiles a nd electrophiles a re reaction int ermediates ha ving electron r ichan d electron deficient centres respectively. Hence, th ey tend to att ack electron

    deficient an d electron rich cen tres resp ectively. Clas sify th e followin g sp eciesas electrophiles an d n u cleophiles.

    (i) H3CO

    (ii) (iii) (iv)

    (v) (H3C)

    3C

    +(vi) Br

    (vii) H

    3COH (viii) RNHR

    3 3 . The r elative rea ctivity of 1, 2 , 3 h ydrogens towards chlorina tion is 1 : 3 .8 : 5.

    Calculate the percentages of all monochlorinated products obtained from2-methylbutane.

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    3 4 . Write the stru ctures an d n am es of produ cts obtained in the reactions of sodiu mwith a m ixtu re of 1-iodo-2-meth ylpropa ne a nd 2-iodopropa ne.

    3 5 . Write hydrocarbon radicals that can be formed as intermediates dur ing

    mon ochlorin ation of 2-m eth ylpropa n e? Wh ich of th em is more sta ble? Givereasons .

    3 6 . An alkan e C8H

    18is obta ined a s th e only produ ct on su bjecting a p rimary alkyl

    ha lide to Wurtz reaction. On mon obromina tion th is alkan e yields a s in gle isomer

    of a tertiary bromide. Write th e stru ctu re of alkan e and t he tertiary bromide.

    3 7 . Th e rin g syst ems h avin g followin g cha ract eristics are arom at ic.

    (i) P lana r r ing conta in ing conjuga ted bonds .

    (ii) Complete delocalisa t ion of the electron s in ring syst em i.e. eachatom in the r ing has u nh ybridisedp-orbital, an d

    (iii) Presence of (4n+2)electrons in t he ring where n is a n int eger(n = 0, 1 , 2,...........) [Hu ckel ru le].

    Using th is informa tion class ify the following compou nds as aroma tic/ nonaroma tic.

    3 8 . Wh ich of th e followin g compou n ds are arom atic according to Hu ckels ru le?

    (A) (B) (C)

    (D) (E) (F)

    3 9 . Suggest a route to prepare ethyl hydrogensulphate (CH3CH

    2OSO

    2OH)

    st art ing from eth an ol (C2H

    5OH).

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    1 6 8Exemplar Problems, Chemis t ry

    IV. Matching Type

    4 0 . Match th e reagent from Colum n I which on reaction with CH3CH=CH

    2gives

    som e produ ct given in Colu mn II as per th e codes given b elow :

    Co lum n I Co lum n II

    (i) O3/ Zn + H

    2O (a) Acetic a cid a n d CO

    2

    (ii) KMn O4/ H+ (b ) Pr op a n -1 -ol

    (iii) KMn O4/ OH (c) Pr op a n -2 -ol

    (iv) H2O/ H+ (d) Aceta ldehyde and formaldehyde

    (v) B2H

    6/ Na OH an d H

    2O

    2(e) Pr op a n e -1 ,2 -d iol

    4 1 . Match th e hydrocarb ons in Colum n I with th e boiling points given in Colu mn II.

    Colum n I Co lum n II

    (i) nPen tan e (a ) 282 .5 K

    (ii) is o-Pen ta n e (b ) 309 K

    (iii) neo-Pen ta n e (c) 301 K

    4 2 . Match th e following reacta n ts in Colu mn I with th e correspond in g reactionprodu cts in Colu mn II.

    Colum n I Co lum n II

    (i) Ben zen e + Cl2 3AlCl (a ) Ben zoic a cid

    (ii) Ben zen e + CH3Cl 3AlCl (b ) Me thy l phe nyl ketone

    (iii) Ben zen e + CH3COCl 3AlCl (c) Tolu en e

    (iv) Tolu en e 4KMn O / N a OH

    (d ) Ch lor ob en zen e

    (e) B enze ne he xa c h lo ride

    4 3 . Match th e reactions given in Colu mn I with th e reaction types in Colu mn II.

    Colum n I Co lum n II

    (i) CH2

    CH2

    + H2O

    +H

    CH3CH 2OH (a) Hydrogen a tion

    (ii) CH2

    CH2

    + H2 Pd CH 3CH3 (b ) Ha logen a tion

    (iii) CH2

    CH2

    + Cl2 ClCH2CH2Cl (c) Polym erisa t ion

    (iv) 3 CH CH Cu tube

    H e a tC

    6H

    6(d ) Hydra tion

    (e) Con den sa tion

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    1 6 9 H ydroca rbons

    V. Assert ion and Reas on Type

    In th e following quest ions a st atem ent o f asse rtion (A) followed by a stat em en t

    of reason (R) is given. Choose the correct opt ion out of the choices givenbelow each quest ion.

    4 4 . As s er t ion (A) : The compound cyclooctane has the fol lowing structuralformu la :

    It is cyclic a n d h as conjugated 8-electron s ystem bu t it is n otan aromatic compoun d.

    Rea s on (R) : (4n + 2) electrons r u le does n ot hold good an d ring is n ot

    planar.

    (i) Both A an d R are correct and R is th e correct explan ation of A.

    (ii) Both A an d R are correct bu t R is n ot the correct explan ation of A.

    (iii) Both A and R a re not cor rect .

    (iv) A is n ot cor rect bu t R is correct .

    4 5 . As s er t ion (A) : Tolu ene on Friedal Crafts met h ylation gives o an d pxylene.

    Rea s on (R) : CH3-grou p bond ed to benzene rin g increases electron den sity

    a t o an d p position .

    (i) Both A an d R are correct and R is th e correct explan ation of A.

    (ii) Both A an d R are correct bu t R is n ot the correct explan ation of A.

    (iii) Both A and R a re not cor rec t .

    (iv) A is n ot cor rect bu t R is correct .

    4 6 . As s er t ion (A) : Nitration of benzene with nitric acid requires the use ofconcentra ted su lphu ric acid.

    Rea s on (R) : The m ixtur e of concentra ted su lphu ric acid and concen trated

    n itric acid prod u ces th e electroph ile, NO2

    + .

    (i) Both A an d R are correct and R is th e correct explan ation of A.

    (ii) Both A an d R are correct bu t R is n ot the correct explan ation of A.

    (iii) Both A and R a re not cor rect .

    (iv) A is n ot cor rect bu t R is correct .

    4 7 . As s er t ion (A) : Among isomeric penta nes, 2 , 2-dimeth ylpenta ne ha s highestboiling point .

    Rea s on (R) : Bran ching does not affect th e boilin g poin t.

    (i) Both A an d R are correct and R is th e correct explan ation of A.

    (ii) Both A an d R are correct but R is n ot the correct explan ation of A.

    (iii) Both A and R a re not cor rec t .

    (iv) A is n ot cor rect bu t R is correct .

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    1 7 0Exemplar Problems, Chemis t ry

    VI. Long Answe r Type

    4 8 . An alkyl ha lide C5H

    1 1Br (A) rea cts with eth an olic KOH to give an alk en e B,

    which reacts with Br2 to give a com pou n d C, which on deh ydrobr omin at iongives a n alkyne D. On tr eatm ent with sodiu m m etal in liqu id am mon ia one

    m ole of D gives on e m ole of th e sod iu m s alt of D an d h alf a m ole of h ydr ogen

    gas . Complete h ydrogena tion of D yields a s tra igh t ch ain a lkan e. Iden tify

    A,B, C an d D. Give th e react ion s invovled.

    4 9 . 896 mL vap our of a h ydrocarbon A ha ving carbon 87.80 % an d h ydrogen

    12 .19 % weighs 3.2 8g at STP. Hydrogenat ion of A gives 2-m eth ylpen ta n e.

    Also A on h ydra tion in t h e pr es en ce of H2SO

    4an d HgSO

    4gives a ket on e B

    having molecular formula C6H

    1 2O. Th e ke ton e B gives a pos itive iodoform

    tes t. Find th e st ru ctu re of A an d give th e reaction s in volved.

    5 0 . An u n sa tu rated hydrocarb on A add s t wo molecules of H2

    an d on reductive

    ozonolysis gives bu tan e-1,4-dial, etha na l an d propan one. Give the stru ctu re

    of A, write its IUPAC n am e a n d e xplain th e rea ctions involved.

    5 1 . In th e presen ce of peroxide ad dition of HBr to propen e tak es place according

    to an ti Mar kovnikovs ru le bu t peroxide effect is n ot seen in th e cas e of HCl

    an d HI. Explain .

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    1 7 1 H ydroca rbons

    ANSWERS

    I. Mult ip le Ch oice Qu es t ions (T y p e-I)

    1. (iv) 2. (i) 3. (ii) 4. (i) 5. (i) 6. (iv)

    7. (iii) 8. (ii) 9. (iv) 10 . (iii)

    II. Mul t ip le Ch oice Qu es t ion s (Ty p e-II)

    11 . (iii), (iv) 12 . (iii), (iv) 13 . (iii), (iv)

    14 . (i), (iv) 15 . (i), (iii) 16 . (i), (iii)

    17 . (i), (iii) 18 . (i), (iii) 19 . (ii), (iii)

    III. S h or t An s w er Ty p e

    20 . Both alkenes and arenes are electron-rich. Therefore u ndergo electrophilic

    reactions . Olefins u n dergo ad dition reactions b ecau se add ition of a reagentto an olefin gives a more st able produ ct as s p2 hybridisa t ion cha nges to

    s p 3 hybridisation. Addition to th e dou ble bond of an aren e wou ld give aproduct with less or no resonance stability hence addition is difficult

    arenes. On the other h an d in su bstitution reaction resonan ce stabilisation

    is retained th erefore, aren es u nd ergo su bstitu tion reaction.

    21 . 2-Butene i s capable of showing geometr ica l isomer ism.

    22 . The rota t ion about CC bond is restr icted becau se of repulsion betweenelectron clou d of CH bond s on eith er carbon atom s.

    24 . Bond dissocia t ion en ergy is least for HI an d ma ximu m for HCl therefore,

    ord er of rea ctivity will be HI > HBr > HCl.

    25 . P ropyl c h lo r ide fo r m s le s s s t a b le C H3CH

    2CH

    2

    carbocation with

    anhydrous AlCl3

    which rea r ranges to a more s tab le

    carbocation a nd gives isopropylben zen e as th e produ ct of th e reaction.

    27 . The +R effect of OCH3

    > Cl an d NO2h as a R effect. Relative reactivity

    of th e su bs tituted ben zen e rin gs is as follows :

    C6H

    5OCH

    3> C

    6H

    5Cl

    > C

    6H

    5NO

    2

    28. Halogens a t ta ched to benzene r ings exer t I an d +R e ffec t . +R e ffec t

    domina tes I effec t and inc reases th e e lec t ron d ens i ty a t or th o andpa ra posi t ions of the b enzene r ing with respect to halogens .

    33 . 2-Methyl butan e is . Poss ib le compoun ds a re A, B

    an d C given below :

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    1 7 2Exemplar Problems, Chemis t ry

    Nin e pos sibilities for comp ou n d A

    because nine methyl hydrogensare present in 2-meth ylbu tan e.

    Two p oss ibilities for B com pou n d

    because two CHhydr oge ns a r e

    present in 2-methylbu tan e.

    O n l y o n e p o s s i b i l i t y f o r C

    c om p o u n d b e c a u s e o n e C H

    h y d r o g e n i s p r e s e n t i n 2 -

    methylbutane.

    Relat ive am ou n ts of A, B

    and C compoun ds= n u m ber of h ydrogen relative react ivity

    A (1 ) B (2 ) C (3 )

    Rela tive a m ou n t 91= 9 23.8 = 7 .6 15=5

    Total Amou nt of mo noh aloginated com pounds = 9 + 7.6 + 5 = 21 .6

    Percen ta ge of A = 9

    10 02 1 . 6

    = 41.7 %

    Percen ta ge of B =7.6

    10 021 .6

    = 35.2%

    Percen ta ge of C =5

    10 021 .6

    = 23.1 %

    3 5 .

    Radical I is tertiary where a s r ad ical II is p rimar y. Rad ical I is m ore sta ble

    du e to hyperconjugation.

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    1 7 3 H ydroca rbons

    3 6 .

    3 7 . A = Pla na r rin g, a ll a tom s of th e rin g s p 2 hybridised, h as six delocalised electron s, follows Hu ckel ru le. It is a rom atic.

    B = Ha s s ix electrons , but th e delocalisation stops a t s p 3 hybridised

    CH2- carbon. Hence, not aroma tic.

    C = Six deloca lis ed -electrons (4 electrons + 2 un sh ared electrons on

    n egatively cha rged carb on) in a p lan ar ring, follows Hu ckels r u le.

    It is arom atic.

    D = Ha s on ly fou r deloca lis ed -electrons. I t is n on a romat ic.

    E = Six deloca lis ed -electron s follows Hu ckels ru le. electrons are ins p 2 hybridised orbitals, conjugation all over th e ring becau se of

    positively cha rged carb on. Th e rin g is plan ar h ence is arom atic.

    F = Follows Hu ck els ru le, h a s 2 electrons i.e. (4n +2) -electrons where

    (n =0), d elocalised -electrons . It is ar oma tic.

    G = 8 electron s, d oes n ot follow Hu ckels ru le i.e., (4n +2) -electronsru le. It is not a roma tic.

    3 8 . A = Has 8 electron s, does not follow Hu ckel ru le. Orbita ls of one carbonatom are n ot in con jugation . It is not ar omat ic.

    B = Ha s 6 delocalised electrons . Hence, is arom atic.

    C = Ha s 6 electrons in conjugation bu t n ot in t he ring. Non a romatic.

    D = 10 electrons in plan ar rings, aroma tic.

    E = Ou t of 8 electrons it has delocalised 6 electrons in one sixmem bered p lana r ring, which follows Hu ckels ru le du e to which it

    will be a rom at ic.

    F = 14 electrons a re in conju gation a nd are pres ent in a ring. Huckelsru le is b ein g followed. Compou n d will be ar oma tic if ring is plan ar.

    IV. Ma t ch ing T y p e

    4 0 . (i) (d ) (ii) (a ) (iii) (e) (iv) (c)

    (v) (b)

    4 1 . (i) (b ) (ii) (c) (iii) (a)

    4 2 . (i) (d ) (ii) (c) (iii) (b) (iv) (a)

    4 3 . (i) (d ) (ii) (a ) (iii) (b) (iv) (c)

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    1 7 4Exemplar Problems, Chemis t ry

    V. Ass er t ion an d Reas on Typ e

    44 . (i) 45 . (i) 46 . (i) 4 7. (iii )

    VI. Long Answer Type

    48 . C5H

    11Br

    alc.KOH Alken e (C5H

    1 0) 2 2

    B r in CSC

    5H

    1 0Br

    2

    (A) (B) (C)

    Alc.KOH2HBr

    C5H

    8

    3Naliq.NH

    C

    5H

    7Na +

    1

    2H

    2

    D (Alkyn e) Sod iu m a lkylide

    Th e reac t ions su gges t th a t (D) i s a te rm ina l a lkyn e . This means t r ip lebond is a t th e end of the cha in. I t cou ld b e e i th er (I ) or (I I).

    CH3 CH

    2CH

    2CH

    2CH

    I II

    Since alkyne D on h ydrogen ation yields s tra igh t ch ain a lkan e, thereforestru ctu re I is the s tru ctu re of alkyne (D).

    Hence, th e stru ctu res of A, B an d C are a s follows :

    (A) CH3CH

    2CH

    2CH

    2CH

    2Br

    (B) CH3CH

    2CH

    2CH CH

    2

    (C) CH3CH

    2CH

    2CH (Br)CH

    2Br

    4 9 . Step I

    896 mL vap our of CxH

    y(A) weigh s 3.2 8 g

    227 00 m L vapou r of CxH

    y(A) weigh s

    13.2822700g mol

    8 9 6= 83.1 g mol1

    Step II

    Ele m en t (%) Atom ic Rela tive ra tio Rela tive n o. S im ples tm a s s of a tom s ra tio

    C 87 .8 1 2 7.31 1 3

    H 1 2 .1 9 1 12 .1 9 1 .66 4.98 5

    Em pir ical form u la of A C3H

    5

    Em pirical formu la ma ss = 35 + 5 = 41 u

    n = Molecu la r m ass 83 .1

    = = 2.0 2 2Em piric a l form ula m ass 41

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    1 7 5 H ydroca rbons

    Molecular m as s is dou ble of th e empirical formu la m as s.

    Molecular Form u la is C 6H 1 0

    S tep III

    Stru ctu re of 2-meth ylpen tan e is

    Hence, the molecu le h as a five carbon ch ain with a m ethyl group a t th esecond carbon a tom.

    A a dd s a m olecu le of H2O in th e presen ce of Hg 2+ a n d H+, it sh ould be an

    alkyn e. Two pos sible st ru ctu res for A ar e :

    or

    I II

    Since th e keton e (B) gives a pos itive iodoform t est, it sh ou ld conta in a

    COCH3

    grou p. Hence th e stru ctu re of ketone is a s follows :

    Th erefore str u ctu re of alkyn e is II.

    50 . Two molecu les of h ydrogen a dd on A th is sh ows tha t A is eith er an

    alkadiene or a n a lkyne.

    On reductive ozonolysis A gives three fragments, one of which is

    dialdehyde. Hen ce, the m olecule ha s b roken down a t two sites. Th erefore,

    A h as two dou ble bon ds . It gives t h e following th ree fra gmen ts :

    OHCCH2CH

    2CHO, CH

    3CHO an d CH

    3COCH

    3

    Hence, its s tru cture as d educed from the th ree fragments m u st be

    (A)

    Rea ct ion s

    (A) Ozone

    2Zn / H O CH3CHO + OHCCH

    2CH

    2CHO +