Hydrocarbons Practice Sheet

Hydrocarbons|Comp2014
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1.
An organic compound (A) C6H10 on reduction, first give (B) C6 H12 and finally (c) C6 H14 . (A) on reaction with ozone followed by hydrolysis in presence of Zn gives two aldehydes C 2 H 2 O 2 (E). Oxidation of (B) with acidified KMnO 4 gives acid (F) C3 H 6 O 2 . Determine structures of (A) to (F) withproperreasoning. Identify (a) the chiral compound C, C10 H14 , that is oxidized with alk. KMnO 4 to PhCOOH,and(b)theachiralcompoundD, C10 H14 ,inerttooxidationunderthesamecondition. Analkylhalide,(X),offormula C6 H13Cl ontreatmentwithpotassiumtertiarybutoxidegivestwo isomeric alkenes Y and Z (C6 H12 ) . Both alkenes on hydrogenation gives 2, 3dimethylbutane. PredictthestructuresofX,YandZ. a)
Ph H
+ Br2 (A)
2.
3.
4.
CH3
HBr/peroxide
(B)
Identify A and B b) Write the product(s) of the following reactions: Peroxide CH3CH = CH 2 + BrCCl3 ?
5.
Write the major products of the hydroboration and oxidation of: a) 1-Ethyl cyclopentene b) Methylene cyclopentene. Give the missing compounds in the following: a) BH .THF CH COOH
3 3 ? ?
6.
b) c) d) 7.
BH3 .THF CH3COOH ? ?

BH3 .THF CH3COOH ? ?
(i) BH 3 .THF ? (ii) CH 3COOH
Complete the following equation: H2 H2 (A) CH3CH 2CH 2CH3 a) CH3C CCH3 Pt Pt
Na +C2 H5 OH b) CH3 C CCH3 (B) + NaOC2 H 5
8. 9.
a) Starting with any alkyne, prepare ethyl cyclohexyl ethyne. b) Starting with cyclohexyl ethyne, prepare acetyl cyclohexane. a) Complete the following reactions:
Al2 O3 , NaNH 2 C2 H 2 H 2 (1 equiv) H CH 3COCH3 A B C D E Pd 400 C
+
b) Complete the following reactions:

i) NaNH 2 H2 CH 2 I 2 CH3 C CH A B C ii) CH3 CH 2 Br Lindlar's catalyst Zn (Cu )
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10
CH3
HCO3 H X KMnO 4 , Y
O3 , H 2 O Z (mix)
Identify X, Y and Z
1. Predicttheproductofthefollowing
a) b)
H3C
OH CH3
conc. H 2SO 4 / A HCl B
H2O / H A
CH2 CH3
(i) B2 H 6 B (ii) H O (OH )

2 2
C
(i) Hg(OAc)2 (ii) NaBH 4
c)
OH
RCO3H H 2O H J +
2.
a) Givereasonsforthefollowing: When 1penten 4yne is treated with HBr in equimolecular proportion, the addition takes place on double bond and not on triple bond yielding thereby the product CH3CH(Br)CH2CCH.
b) Provideasuitablemechanismforthefollowingreaction.
OH CH3 CH3
3. Three isomeric alkenes A, B and C, ( C5 H10 ) are hydrogenated to yield 2methylbutane A and B gave the same 3 ROH on oxymercuration demercuration B and C give different 1 ROHs on hydroborationoxidationsupplythestructuresofA,BandC. 3,3dimethyl1buteneandHlreacttogivetwoproducts, C6 H13l .Onreactionwithalc.KOHone isomer, (I) gives back 3, 3dimethyl1butene the other (J) gives an alkene that is reductively ozonizedto Me 2 C = O .Givethestructuresof(l)and(J)andexplaintheformationofthelatter. a) Identify X, Y and Z in the following sequence of reactions giving stereo chemical structures whereverpossible.
(i) CH3CO3 H (i) H 2 (i) Na C CH (X) (Y) (Z) (ii) Br Pd BaSO4 (ii) H + / H O
2
4.
5.
b) Completethefollowingsequences
i) ii)
6.
AlCl3 + CH 3 CH 2 CH 2 Cl
Br2 i) NaNH 2 (3 equi.) C 6 H 5CH = CH 2 A B ii) CH 3 I
Hydrocarbon (A) C6 H10 on treatment with H 2 / Ni , H 2 / Pd BaSO 4 and Na/liquid NH3 forms three different reaction products (B), (C) and (D) respectively. (A) does not form any salt with ammoniacal AgNO3 solution but forms a salt (E) on heating with NaNH 2 in an inert solvent. CompoundEreactswith CH 3 I togive(F).Compound(D)onoxidativeoznolysisgivesnbutanoic acidalongwithanotherproduct.Givestructuresof(A)to(F)withproperreasoning. A hydrocarbon (A) containing 90% carbon reacts with dil. H 2SO 4 in presence of HgSO 4 to give (B). Compound (B) is reduced by LiAlH 4 to (C) which on heating with H 2SO 4 gives (D) directly byhydrogenationinpresenceofdeactivatedPd CaCO3 catalyst.Outlinethereactions. Identifythemissingcompoundinthefollowingsequenceofreaction:
7.
8.
i) ii)
H2O H2 Br2 NaNH 2 KOH (alc.) CaC 2 (A) (B) (C) (D) (E) Lindlar 's catalyst H+
4H 2 O LiAlH 4 Conc. H 2SO 4 Br2 H / Hg Mg 2 C3 (A) (B) (C) (D) H 2O NaNH 2 (E) (F)
2+
iii)
9.
Br2 / h Br2 / CCl4 KMnO 4 alcoholic KOH alcoholic KOH CH3CH 2 CH 2 CH 3 A B C D E 1 mol H+
An hydrocarbon (A), C8 H14 , decolourises Br2 / CCl4 and cold dil. neutral KMnO 4 solution, but does not react with ammonical AgNO3 and Cu 2 Cl2 solutions. It on ozonolysis produced two molecules of the same acid (B), C 4 H 8O 2 , which on heating with sodalime gave propane. What are(A)and(B)? A hydrocarbon (A) is treated with excess of HCl to give a dihalogen compound (B), which on treatment with alc. KOH and aq. KOH separately gives (A) and (C) respectively. (C) can also be obtained by heating calcium salt of 2methyl propanoic acid with calcium acetate. What are (A), (B)and(C)? a) Suggest appropriate structures for the missing compounds. (The no. of carbon atoms remainsthesamethroughoutthereactions)
CH3
dil. H 2SO4 HlO4 OH A B C
10.
1.
CH3
O3 / Zn / H 2 O
b)
excess H 2 / Pd Br2 / CCl4 1-isopropyl-4-methyl Limonene decolourised solution
cyclohexane
O
CH 2O +
(1 mole)
O CH3
(1 mole)
H3C
H O
IdentifythestructureofLimonene.
H3C O
H3O A. Identify A.
+
c)
NO2
2.
Identifytheunknownalkeneinthefollowingreactions.
(i) O3 a) (A) CH 3COCH 3 + CH 3CH(CH 3 )CHO (ii) Zn / CH3COOH
(i) KMnO4 / OH CH3COCH 2 CH 2 CH 2 CH 2 COOH b) (B) (ii) H O+

3
(i) O3 c) (C) 2CH 3CH 2 CO 2 H (ii) H 2 O
(i) KMnO4 / OH CH3CH 2 COOH + CH3CH 2 CH 2CH 2 COOH d) (D) (ii) H O+

3
O
+ CH 2 O
3.
(i) O3 e) (E) (ii) Zn / AcOH
Compound A (C6 H12 ) is treated with Br2 to form compound B (C6 H12 Br2 ) . On treating B with alcoholic KOH followed by NaNH 2 the compound C(C6 H10 ) is formed C on treatment with H 2 / Pt forms 2methylpentane. The compound `C does not react with ammoniacal Cu 2 Cl2 or AgNO3 . When A is treated with cold KMnO 4 solution, a diol D is formed which gives two acids E and F when heated with KMnO 4 solution. Compound E is found to be ethanoic acid. Deduce thestructuresfromAtoF. Alkenes(A)and(B)yieldthesamealcohol(C)onhydration.Onvigorousoxidationwith KMnO 4 , A gives a carbonyl compound (D) and an acid (E) each containing 4 carbon atoms. On the other hand (B) gives an acid (F) and a carbonyl compound (G) no two identical groups are attached to thesamecarbonatom.Givestructureof(A)to(G)withproperreasoning. An alkane (A) with M.F. C6H14 reacts with chlorine in the presence of U.V light to yield three isomeric monochloro derivatives (B), (C) and (D). Of these only (C) and (D) undergo dehydrohalogenation with sodium ethoxide in ethanol to produce an alkene. Moreover (C) and (D) yields the same alkene (E) (C6H12). Hydrogenation of (E) produces (A). Treating (E) with HCl
4.
5.
producesacompound(F)thatisanisomerof(B),(C)and(D).Treating(F)withZnandaceticacid givesacompound(G),whichisisomericwith(A).Proposestructuresfor(A)to(G). 6. A certain hydrocarbon (A) was found to contain 85.7% carbon and 14.3% hydrogen. This compound consumes one mole of H 2 to give a saturated hydrocarbon (B). One gm. Of hydrocarbon (A) just decolourised 38.05 gm of 5% solution by mass of Br2 in CCl4 . Compound (A) on oxidation with concentrated KMnO 4 gave compound (C) ( C 4 H 8O ) which could be preparedbythereactionofacidic HgSO 4 solutionon2butyne.Deducethestructuresof(A),(B) and(C). Two isomeric alkyl bromides (A) and (B), C5 H11Br yield the following results in the laboratory. (A)ontreatmentwithalcoholicKOHgives(C)and(D) C5 H10 (C)onozonolysisgivesHCHOand2 methyl propanal. (B) on treatment with alcoholic KOH gives (D) and (E), C5 H10 . All compounds (C),(D)and(E)oncatalytichydrogenationgive(F), C5 H12 .Deducestructuresof(A)to(F).
7.
8. There are six different alkenes A, B, C, D, E and F. Each on addition of one mole of hydrogen gives G which is the lowest molecular wt. hydrocarbon containing only one asymmetric carbon atom.Noneoftheabovealkenegiveacetoneasaproductonozonolysis.GivethestructureofA toF. An alkane (A), C5 H12 , on monochlorination at 300C gives a mixture of four monochlorinated derivatives (B), (C), (D) and (E). Two of these derivatives give same stable alkene (F) on dehydrohalogenation. Onoxidationwithhotalkaline KMnO 4 ,followedbyacidification(F)gives twoproducts(G)and(H).Givestructuresof(A)to(H)withproperreasoning.
9.
10.
a)
CH3
PCl5 NaNH 2 A B. Identfy A and B. H+
b) Showtheproductsofthesereactions:
i)
Br CH2
NaNH 2 / HCl(excess)
CH3
ii)
CH3 Br Br
EtOK / EtOH
1.
Whengas(A)ispassedthroughdryKOHatlowtemperature,adeepredcolouredcompound,(B) and a gas (C) are obtained. The gas (A), on reaction with but2ene, followed by treatment with Zn/H2Oyieldsacetaldehyde.Identify(A),(B)and(C). [IIT1994]
2.
1,4pentadiene reacts with excess of HCl in the presence of benzoyl peroxide to give compound (X) which upon reaction with excess of Mg in dry ether forms (Y). Compound (Y) on treatment withethylacetatefollowedbydiluteacidyields(Z).Identifythestructuresofcompounds(X),(Y) and(Z). [IIT1995] An organic compound E (C5H8) on hydrogenation gives compound F(C5H12). Compound (E) on ozonolysisgivesformaldehydeand2ketopropanal.Deducethestructuresofcompound(E). [IIT1995] A hydrocarbon (A) of the formula C8H10, on ozonolysis gives compound (B) (C4H6O2) only. The compound (B) can also be obtained from the alkyl bromide (C) (C3H5Br) upon treatment with magnesium in dry ether, followed by carbon dioxide and acidification. Identify (A), (B) and (C) andalsogiveequationsforthereactions. [IIT1996] The hydrocarbon (A), adds one mole of hydrogen in the presence of a platinum catalyst to form nhexane. When (A) isoxidized vigorously with KMnO4, a single carboxylic acid, containing three carbonatoms,isisolated.GivethestructureofAandexplain. [IIT1997] A hydrocarbon (A) of molecular weight 54 reacts with an excess of Br2 in CCl4 to give a compound (B) whose molecular weight is 593% more than of (A). However, on catalytic hydrogenationwithexcessofhydrogen,(A)forms(C)whosemolecularweightisonly7.4%more thanthatof(A).(A)reactswithCH3CH2BrinthepresenceofNaNH2togiveanotherhydrocarbon (D)whichonozonolysisyieldsdiketone(E).(E)onoxidationgivespropanoicacid.Givestructures of(A)to(E)withreasons [Roorkee1997] Completethefollowingreaction.
3.
4.
5.
6.
7.
i)
CH2
1 2 3
[IIT 1999]
ii)
CH3
H2 Major product Lindlar catalyst
[IIT 2001]
iii)
H3C
CH3
C 2 H5 OH Major product
CH3
Br
[IIT 2001]
8. 9.
a) Explain briefly as to why alkynes are generally less reactive than alkenes towards electrophilicreagentssuchas H + . b) Explainwhythecentralcarboncarbonbondin12butadieneisshorterthaninbutane.
In alkyl halide X of formula C6 H13Cl on treatment with potassium tertiary butoxide gives two isomeric isomeric alkenes Y and Z (C6 H12 ) . Both alkenes on hydrogenation gives 23dimethylbutane.PredictthestructuresofX,YandZ. Give the structures of two major products from 3ethylpent2ene under each of the following reactionconditions
10.
a) HBrinpresenceofperoxide b) Br2 / H 2 O .
Objective
1. 2. 3. Onheating CH 3COONa withsodalimethegasevolvedwillbe (a) C2 H 2 (c) C2 H 6 (b) CH 4 (d) C2 H 4 .
Whichofthefollowingwillhaveleasthinderedrotationaboutcarboncarbonbond? (a) Ethane (c) Acetylene (b) Ethylene (d) hexachloroethane.
A sample of 1.79 mg of a compound of molar mass 90 g mol 1 when treated with CH 3 Mgl releases1.34mlofagasatSTP.Thenumberofactivehydrogeninthemoleculeis
4. 5. 6.
(a) 1 (c) 3
(b) 2 (d) 4.
Theadditionof Br2 totrans2buteneproduces (a) (+)2,3dibromobutane (c) rac2,3dibromobutane (b) ()2,3dibromobutane (d) meso2,3dibromobutane
ThetreatmentofCH3C(CH3)=CHCH3with NalO 4 orboiling KMnO 4 produces (a) CH 3COCH 3 + CH 2 O (c) CH 3COCH 3 + CO 2 (b) CH 3CHO + CH 3CHO (d) CH 3COCH 3 + HCOOH .
What is the chief product obtained when nbutane is treated with bromine in the presence of lightat130C?
CH3
(a)
H 3C
Br
(b)
H 3C
Br
H 3C
CH3
(c)
CH3
Br
(d)
H3C
C CH3
CH2 Br
7.
Theolefin,whichonozonolysisgives CH 3CH 2 CHO & CH 3CHO . (a) But1ene (b) But2ene

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(d) Pent2ene.
8. 9.
(c) Pent1ene Additionofhalogenacid(HX)isleastin (a) CH 2 = CHCl (c) CH 3 CH = CH 2
(b) CH 2 = CH 2 (d) (CH 3 ) 2 C = CH 2 .
Which of the following alkene will react fastest with H 2 under catalytic hydrogenation condition?
R R
(a)
H R H R
(b)
H R R R
R
(c)
R H
(d)
R
10.
Productsofthereaction,
CH3 H3C CH3
CH3
D2 O / D CH2
+
CH3 CH3
(a)
H3C CH3 OD
CH2D
(b)
H3C OD
CH3
CH2D
CH3 H
(c)
H3C OD D
CH3
(d)
H3C CH3 D
CH2 OD
1.
Pointout(A)inthegivenreactionsequence:
O3 / H 2 O (A) (B) 2CH 3COOH + CO 2
(a) (c)
2. Endproductofthefollowingsequenceis:
(b) (d)
H 2O Heat Hg CaO + C (A) (C) (C) H 2SO4
2+
(a) Ethanol
(b) Ethylhydrogensulphate
(d) Ethyleneglycol.
3.
(c) Ethanal Hydrogenationofthecompound

H3C
Me H H
Me H
4.
Inthepresenceofpoisonedpalladiumcatalystgives: (a) Anopticallyactivecompound (c) Aracemicmixture (b) Anopticallyinactivecompound (d) Adiastereomericmixture.
Thetreatmentof C 2 H 5 Mgl withwaterproduces (a) Methane (c) Ethanal

H3C CH3
Br
(b) Ethane (d) Ethanol.
5.
CH2
+ HBr A. (predominant), A is
(a)
H3C CH3 Br
H 3C
CH3
CH CH3
(b)
CH2
Br
(c) 6.
7. 8.
H3C
C CH3
CH2 CH3
(d)
None of these.
Br H3C CH3 CH3
When isobutene is brominated, the percentage of

(a) 0% (c) 10%
would be
(b) 83% (d) 100%
Whichofthefollowingisusedforaromatizationofnhexane? (a) AlCl3 (c) Cr2O3/Al2O3withheat (b) NainliquidNH3 (d) Wilkinsonscatalyst
Identify(B)inthefollowingsequenceofreactions.
Cu 2 Cl2 + NH 4 Cl HCl CH CH (A) (B)
(a) (c)
CH 3CH 2 Cl
(b) CH3 Cl (d)
HC
CH 2 = CH CH 2 CH 2 Cl Cl
H2C
CH2
9
9. 10.
Propene can be converted into 1propanol by oxidation. Which set of the reagents is used to effecttheconversion? (a) OsO4CHCl3 (c) AlkalineandcoldKMnO4 (b) O3/ZnH2O (d) B2H6andalk.H2O2.
Inthefollowingsequenceofreactions,identifytheproduct(D).
NaNH 2 HBr HBr alk. KOH CH CH (A) (B) (C) (D)
(a) Ethanol (c) Ethanal
(b) Ethyne (d) Ethene.
10

Hydrocarbons Practice Sheet

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Hydrocarbons|Comp2014

BH3 .THF CH3COOH ? ?

b) Complete the following reactions:

conc. H 2SO 4 / A HCl B

(i) B2 H 6 B (ii) H O (OH )

Br2 i) NaNH 2 (3 equi.) C 6 H 5CH = CH 2 A B ii) CH 3 I

excess H 2 / Pd Br2 / CCl4 1-isopropyl-4-methyl Limonene decolourised solution

(i) KMnO4 / OH CH3COCH 2 CH 2 CH 2 CH 2 COOH b) (B) (ii) H O+

(i) O3 c) (C) 2CH 3CH 2 CO 2 H (ii) H 2 O

(i) KMnO4 / OH CH3CH 2 COOH + CH3CH 2 CH 2CH 2 COOH d) (D) (ii) H O+

(i) O3 e) (E) (ii) Zn / AcOH

PCl5 NaNH 2 A B. Identfy A and B. H+

Whichofthefollowingwillhaveleasthinderedrotationaboutcarboncarbonbond? (a) Ethane (c) Acetylene (b) Ethylene (d) hexachloroethane.

Theolefin,whichonozonolysisgives CH 3CH 2 CHO & CH 3CHO . (a) But1ene (b) But2ene

(c) Pent1ene Additionofhalogenacid(HX)isleastin (a) CH 2 = CHCl (c) CH 3 CH = CH 2

(b) CH 2 = CH 2 (d) (CH 3 ) 2 C = CH 2 .

H 2O Heat Hg CaO + C (A) (C) (C) H 2SO4

(c) Ethanal Hydrogenationofthecompound

Inthepresenceofpoisonedpalladiumcatalystgives: (a) Anopticallyactivecompound (c) Aracemicmixture (b) Anopticallyinactivecompound (d) Adiastereomericmixture.

Thetreatmentof C 2 H 5 Mgl withwaterproduces (a) Methane (c) Ethanal

(b) Ethane (d) Ethanol.

When isobutene is brominated, the percentage of

(b) 83% (d) 100%

Whichofthefollowingisusedforaromatizationofnhexane? (a) AlCl3 (c) Cr2O3/Al2O3withheat (b) NainliquidNH3 (d) Wilkinsonscatalyst

(b) CH3 Cl (d)

(a) Ethanol (c) Ethanal

(b) Ethyne (d) Ethene.

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