ALKYL HALIDE ALKYL HALIDE CLASSIFICATION OF HALIDES INGLE CORRECT ANSWER TYPE 1, Which of the following is a Monohalide? (A) CHCL (B) CHCl, (© chloroform (D) Carbon tetrachloride 2. Which of the following is a 2° halide ? cH, (A) CH,-CH,-CH,-Cl (B) ” ScH-cH,-cl a HC’ cH, (©) CH,-CH-CH, (0) CH-¢-cl cl CH, 3. Which of the following is a geminal dihalide? (D) CH,-CHCI, 4. Inwhich of the following halides, halogen atom is not connected with sp” hybridized carbon ? a (A)CH,=CH-Cl (8) CH, ao ' Which of the following is an aryl halide ? a a HCI (A) (9) ©) | CH, 6. — Which of the following is nota vinyl halide? | a cl (A) CH,=CH-Cl o CY (@) 7. Which of the following is not an alkyl halide ? Br F (A) CH,=CH-CH,-I (B) Cl () = CH CH — CH, (C)JEE-ORGANIC CHEMISTRY x 1. »% 10. 11. 12. SOLVENT SINGLE CORRECT ANSWER TYPE Which of the following is a polar protic solvent? (A) DMSO. (B) DMF (©) Water (D) HMPT Which of the following is a polar aprotic solvent? (A) HO (B) NH, (C) Acetone (©) C,HOH Total number of Methyl groups in one molecule of HMPT is- (A)5 (B)6 8 (ys Which of the following atom is not present in HMPT ? (A)S (B)P (ON Mc Which of the following solvent does not contain a~CH, group (A) Ethyl alcohol (B) DMF (©) DMA (D) THE When NaCl is dissolved in H,O, Nat is trapped by (A) Cation-dipole interaction (B) Hydrogen bonding (© Electrostatic repulsion (D) Dipole-dipole interaction How many of the following solvent contain atom other than C, H & 0? Acetone, DMSO, HMPT, Ammonia, DMA, DMF, Ethyl alcohol (As (B)6 ©7 (D)8 Total number of polar protic solvents among the following is H,O, NH,, CH,COOH, CH,, CCl,, DME, DMA, HMPT, CH,CH,-O-CH,CH, (a2 (B) 3 ©s5 (D6 Which of the following solvent contain sulfur ? (A) DMSO (B) Acetone (© HMPT (D) DME When NaC! is mixed with polar aprotic solvent, which of the following is not solvated (A) Cation (B) Anion (©) both cation and anion(D) None of these Q 9 0. NZ ‘Tetrahydrofuran ( ] and Sutfotane yee (A) Non polar solvents (B) Polar aprotic solvents (C) Polar protic solvents (D) None of these ‘When an anion is present in water solvent, mostly itis wrapped by (A) Hydrogen bonding (B) Dipole-dipole interaction (C) Electrostatic repulsion (D) Banana bondingALKYL HALIDE NUCLEOP! ES SINGLE CORRECT ANSWER TYPE 1. _ Which of the following order is correct regarding nucleophilicity in polar protic solvent (A) > Cr>Bror (B)b>Br>Cr >F (OF >Br>Ccr >r (D) F>F>Br>cr 2. — Which of the following order is correct regarding nucleophilicity in polar aprotic solvent (A) F-> Ch > Br > (8) > Br > Cr > (OF >Br>Cr >I () b>F>Br>cr 3. Which one of the following has maximum nucleophilicity ? CH, cH, (A) cI (B) HC > cH-0 (©) CH,-CH,-O" (D) BohA&B 4, Which one of the following has maximum nucleophilicity in polar aprotic solvent ? (A) RO- ®) Nu, ocr (©) CHO 5. Which of these statement is INCORRECT about nucleophiles : (A) Nucleophiles have an unshared electron pair and can make use of this to react with an electron deficient species. (B) The nucleophilicity of an element (as electron donor) generally increases on going down a group in the periodic table in polar protic solvent. (A nucleophile is electron-deficient species (D) All good nucleophiles are good bases when we deal across the period. 6 The INCORRECT nucleophilicity order is : (A) (CH);CO- > CH5- (B) PH, > NH (©) CHjCH,CH,O- > (CH,),CO- (D) (CHCH,),N < (CH,CH,),P 7. Which of the following order is correct regarding Nucleophilicity of (0-) in the following compounds © o 0 9 A o 9 8 8 cucH, cH, :0CH, W ( ay (yy (AM>I>I >1V (B)MI>M>I>IV ©)M>I>M>IV () Is IVa Is COJEE-ORGANIC CHEMISTRY 8. % 10. 1. 12. Which of the following order of nucleophilicity is incorrect? (A) H~O—0- > HO (B) Nu, -Nu, > NH, (C) RprimO” > RsecO™ > ReenO™ (D) RprimOH < RyecOH < RieXOH Which of the following order of Nucleophilicity is correct? wl) «fl (B) ws << AA © ral ory! OX Identify correct nucleophi NA a Ny @ | a | am Ss (AO>>a Bd>d)>q@ OM>-an>-a@ Od)>om>aM ity order Identify correct nucleophilicity order oH, NO, CN S oO QO ap QO (aly CQ N N N (AM>dD>aD BM>-d)>O@ OM>d)>q WMah>O>a) Identify correct nucleophilicity order H H Ny N N. © O we 7 a O (A) (>a) > (Dp (B) dD >a) >) (O@>daih> dd (D) GID > (D> dD. Identify correct nucleophilicity order in polar protic solvent (DH,0 (HS (II) HSe (AO>M>a) @)d>d>H) Odd>O>aq@) _© G)>a@>a@ALKYL HALIDE ity order in polar protic solvent (i) NH; (UD) ASH @@O>m>a) &dM>amM>®@ OM>-aM>qM Oda@>o>m 15, Identify correct nucleophilicity order in polar protic solvent, o s Se © O OC AO>@>aD @)M>d>™ OM>aD>q Man>mM>oJEE-ORGANIC CHEMISTRY LEAVING GROUPS SINGLE ANSWER CORREC 1, The correct order of leavability of 'YPE (a) OH (b) ArSOs (c) MeCOO-_ is (A) a H,0 @) 84> Si © herAg we? 8 3. Which one of the following group has maximum leaving ability ? (A) OH® (B) FxcCOO® j@crP (D) F,cso,° 4. Which of the following is best leaving group ? ° 9 (A) -OH (B)-NH, ©-b-o0hy 0)-0-4. 0% 4 5. Consider the following groups: @)—OAc (i) —OMe (ul) -O—SO,—Me (Vv) —O—S0,—CF, The order of leaving group nature is: (AI>I>II>IV (B)IV>II>I>1 (C)UL>1>I>1V (D) > M>1V>1 6. Consider the following species, when attached to sp?-hybridized carbon, their leaving group ability in nucleophilic substitution reactions decreases in the order. ° ° 5 Il tl 2 il oF -8-8 Che oH. 6 on,-€-8 8 } 1 I 7 Iv (A)I>H>IV>M @B)IV>MI>I>0 (OM>I>IV>M = (O)IV>I> 0 >I ! MULTIPLE ANSWER CORRECT TYPE 7. The correct order of leaving group ability is/are “ {O)=s0 > {O)-co (B) oF.s0® > ccs O&m> er (D) 8H, > BH XeALKYL HALIDE 3. KINETICS OF CHEMICAL REACTIONS SINGLE CORRECT ANSWER TYPE Molecularity of a reaction can not be (ayo @)1 ©2 )3 Consider a multistep reaction Ao pe yc sp Which step is Rate determining step (AASB (B)B>C @C+D (D) Insufficient data You are driving on your bike ona four-lane highway and you are likely to come across the following in your path. Identify which of the following would be your rate-determining step? (A) A two-lane fly over (B)A single-lane bridge (C) The four-lane highway itself (D) Cannot be predicted Identify the incorrect statement for the given potential energy profile (A) There are two transition states ed (C) Overall reaction is exothermic (D) Step-1is the rate-determining step Fora reaction: A—==B=—=C Given are : Cis the most stable. B is the least stable. The transition state going from A to B is more stable than the transition state going from B to C. Choose the right diagram for the above facts. (A) i Ze V\ (B) f hn. a B od _/ BS © 3 Reaction progress ‘Reaction progressJEE-ORGANIC CHEMISTRY 6. A hypothetical reaction gives rise two products X and Y. X follows a path with lower activation energy but its free energy contentis very high. ¥ follows a path with high activation energy but its free energy content is very low. Under what condition X will be formed as the major product? (A) Low temperature (B) Slightly high temperature (C) High temperature (D) All of these. (COMPREHENSION TYPE Paragraph For Question no. 7 to 11 Consider following potential energy (PE) profile for a multistep chemical reaction Reactant Product, o Reaction coordinate > Now answer the following questions based on above PE profile 7. Total number of steps in above chemical reaction are (A)2 (B)3 ©4 (D)5 8. Reaction is (A) Exothermic (B) Endothermic (C)Thermoneutral _(D) None of these ‘Total number of transition states formed | (A)3 (B)4 Os (D)6 10. Total number of intermediates formed in above mutlistep chemical reaction (Al (B)2 ©3 (p)4 11. Which step seems to be rate determining step | (A) first (B) second (©) third (D) both second and third Paragraph for question no. 12 to 14 Consider given expression rate = KAP? [B}"? [Cy there A, B and C are reactants in a chemical reaction. Now answer the following questions 12, Whatis order w.rt, to reactant A (ay BLS 2 (p)2.5 | aALKYL HALIDE 13, Whatis order wr. to reactant B (A)-12 (B)O (+12 (D) Negative order is not possible 14. Whatis the overall order of reaction | Al BLS (2.0 @)2.5 Paragraph For Question no. 15 and 16 Consider given potential energy profile and answer following questions Reactant 0 Reaction coordinate (time) > 15. Which product is thermodynamically more stable (AA (B)B (C) Both A & B are equaly stable (D) can not decide 16. Which product will form at faster rate (AA (B)B (C) both A & B (D) can not decide Paragraph For Question no, 17 to 22. Based on the potential energy diagram for some chemical reaction, answer the following questions Potential energy Reaction coordinate 17. _Isthis an endothermic or exothermic reaction? (A) exothermic (B) There is not enough information to determine (© endothermic (D) This reaction can be either exothermic or endothermic 18. What potential energy difference represents the heat of reaction? (AA (B)B @c (D) both A and B a 1 ieJEE-ORGANIC CHEMISTRY 19. tes the location of interme om @OIv 20, Highly unstable transition state is represented by (al BI om ov 21. Which step israte determining step (A) Ist (B) 2nd (©) Both Istand 2nd (D) Can not decide 22, Which of the following statement is correct ? (A) State Tis less stable than transition state II (B) Product is more stable than reactant (© First step is endothermic while second step is exothermic (D) Overall reaction is exothermicALKYL HALIDE REARRANGEMENT OF CARBOCATIONS SINGLE ANSWER CORRECT TYPE Carbocation CH, ~CH, ~CH, rearranges to 1 (A) CH,—-CH-CH, (6) CHs~CH ~CHs oA (D) CH; =CH-CH, | CH; 2. Carbocation CH, - ¢ —CH, tearranges to cn, CHs CH (B) cH-¢ CH,CH; ° © CH, -CH; ~CH, —CH. () CH, -CH, ~CH-CH, ~CH, CH; Il 3. What will be number of @.—H in finally rearranged carbocation if CH;- C —CH,-CH: | I H undergoes rearrangement (A)7 (B)8 ©9 (D) 10 CH H Lod 4. When carbocation CH,~ C —C-CH, undergoes rearrangement to a most stable carbocation, CH, H shifting involved are (A) Two methyl shifts (B) two hydride shifts (C) One methyl and one hydride shift (D) Two methyl & one hydride shift H H \ | 5. When carbocation CH,~C-CH-C-O-CH, undergoes rearrangement, which atom/group will @ hb . ty @) @ am migrate to produce more stable carbocation. (AT (B) 0 om @MIV TTJEE-ORGANIC CHEMISTRY Bae En 6. 10. ‘When following carbocations may undergo rearrangement, hydride shifting may be involved number of carbocation. oO meV amM/Y 109) Iw, 0 w) PY wD Iw, (A)2 (B)3 «4 (@)s Carbocation ‘ee . When rearranges to most stable carbocation, which of the following is not obtained. (A) or (8) or © oO () cr Oo when carbocation undergoes rearrangement, which the following can not be obtained ) Oo @) Or © ©) Cy NZ How many of the following carbocations will undergo rearrangement © Cc a Oe ay ® | + (3 (B)4 (5 (D)6 When carbocation ( ) undergoes rearrangement to most stable carbocation, which of the following statement is INCORRECT about most stable carbocation. (A) Ithas 6 ¢-H (B) Itcontains two methyl groups (©) Itis formed by ring expansion (D) Methyl shifting is involvedALKYL HALIDE Sy1 REACTIONS SINGLE ANSWER CORRECT TYPE 1. Which of the following reactions is not possible ? (A) R-OH+NaBr—+R-Br+NaOH — (B) R-OH+ HBr —>R-Br+H,O (©) Both reactions are possible (D) Both reactions are not possible 2. The rate of solvolysis of tert-butyl bromide will be maximum in which of the following solvents? (A) Et,0 (8) CCl, (C) 00H (D) HO 3. Which of the following factors has no effect on the rate of S,1 reactions ? (A) The nature of the alky! halide (B) The nature of the leaving group (© The concentration of the alkyl halide (D) The concentration of the nucleophile 4, Which of the following is the rate law for S,.1 mechanisms? (A) Rate =k [Alkyl Halide] [Nucleophile] (B) Rate =k [Nucleophile] (© Rate = k [Alkyl Halide] (D) Rate = k [Alkyl Halide] [Nucleophile] + K,[Alkyl Halide] 5. Ph-CH-c)_CHCO.H \ CH, Above reaction is known as: (A) Methanolysis _(B) Ethanolysis (©)Acetolysis (D) Formalysis 6. — Which will give white ppt. with AgNO,? (A) Ca @) (Oya © (O)-cnet (D) Both A & C 7. Which of the following does not produce a white precipitate of AgCl on warming with alcoholic silver nitrate ? (A) Allyl chloride (B)t-Butyl chloride (©) Benzyl chloride (D) Vinyl chloride 8 The increasing order of reactivity of the following halides with AgNO, (11,0 + alcohol) is: (D Cglls - CH = CH-CH,-CH,-Cl (II) C¢Hs CH =CH-CH-CHs | él CeHs (Hl) CgHs -C = CH-CH, -CHy (IV) Cols -d-cHt- chy b b (AMU> 0 (B) WI >I>1 (©) mst (D) I> ml> 1 ‘Assuming no other changes, what is the effect of doubling only the concentration of nucleophile in the following reaction? (CH, ), CBr +l —>(CH,), CI+ Br (A) no change (B) doubles the rate (C)triplesthe rate (D) quadruples the rate ‘Assuming no other changes, what is the effect of doubling both the concentration of the alkyl halide and the nucleophile in the following reaction? (CH,), CBr (A) no change (B) doubles the rate (C) triplesthe rate (D) quadruples the rate —>(CH,), Cl+ Br Which one of the following compounds will be most reactive for Sy1 reactions ? cl I cl Br ) CO ®) CO © CO ©) CO oO Which of the following can not give Sy reaction easily? ee Br Br Br @ & ®) O © oO @) oOALKYL HALIDE 15. Which of followin; q I I I OOO A 16. The order of decreasing Sy1 reactivities of the halides CH, = CHCHCICH, CH,CH,CHCICH, _ , is - I mn M1 (A) l>0> m1 (B)N>1>m ()u>m>1 (D)M>u>1 s least reactive towards Syl ? 17. Arrange the following compounds in order of decreasing rate of hydrolysis for S11 reaction: oO H,-Br a) Hc-{Q)-cH CH, (i) CH,-CH, {O)-ciie ee (vy) cut xO (AI>II>IV>I (B)IV>MI>M>I (QM >IV>M>I_ (D)I>M>M>T 18. Which of the following is most reactive toward Sy1 reaction ? CHCl CHCl CH,-Cl CHy-Cl “O ° @ ° Q ° Q 19. Consider the Sy solvolysis of the following halides in aqueous formic acid: : CH, 7 Br CH, cH-cH-cH, a ” ca’ “ O aly Colts -CH-CoHs av) Br Which one of the following is correct sequence of the halides given above in the decreasing order of their reactivity? (AMI>IV>I>1 @B)M>IV>I>Ml ©l>U>M>IV (D)M>1>1>1VJEE-ORGANIC CHEMISTRY Among the bromides I-III given below, the order of reactivity in $1 reactionis: 0. oO O a O (a O Br Br Br (A) I> I> IL (B)II>T>1 (C)U>M>1 (D) I> 1> 01 21. The correct increasing order of the reactivity of halides for Sy reaction is (A) CH, - CH X < (CH,),CH - X < CH, = CH - CH, - X < PhCH, - X (B) (CH,),CH - X < CH,- CH, ~ X < CH,= CH - CH,X < PhCH, - X (C) PhCH, — X < (CH,)CH - X < CH,- CH,- X < CH, 1H — CH,—X (D) CH, = CH - CH, - X < PH ~ CH, ~X < (CH,),CH ~ X < CH, - CH, ~X H.C Br cH, “\ +, © one & 2, Mon 7 peas : H.C H,0 ~ +Q ow ee CH,+ Cl cH, Boh the rates ry , ry and r, are in the order (A), > 1p > 1; (B)r,>1>1 (n> >r (D) 1, >4,>15 23. Which one of the following will be most reactive for Syj1 reaction ? al Gl e APD dX] Bon-cron, (© Heo cH, ergo hydrolysis by SI mechanism is Kell (© C,H,CH,CI (D) C.H,CH(CH,)C1 24, ‘The compound that does not un (A) CH, = CHCH,CI (B) C, . a ont 28. CT noe vie cH, CH, C1 _ Hou pack Ai OBt | c ty on, fy Bon, Rate Which of the following is correct ? A)R,>R,>R (B)R,>R,>R.21. 29, ALKYL HALIDE the best stereochemical aspects cl the following rea et —H8r_, Product ‘OH (A) Only inversion of configuration occurs at the carbon undergoing substitution. (B) Only retention of configuration occurs at the carbon undergoing substitution (C) Racemization occurs at the carbon undergoing substitution (D) The carbon undergoing substitution is not stereogenic. For the given reaction R R, | I R-c-x —!#_, R-C-OH i 1 R, Ry cH. | (A) CH,-C-Br — (B)CH, =CH-C-Br | | CH, CHs Under identical conditions, solvolysis of which of the following substrates would lead to maximum recemization ? cH ©, apa ©utLa ofa D CH, p Find major product in the following reaction Ci _moitaa;0 .CH,C| E> CH, oH CHOH is Hs (A ors Ha B) 7 ( xX cron © oO) on Which of the following is not expected to be intermediate of the following reaction ? xy