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Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - NEET MCQ


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20 Questions MCQ Test - Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination

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Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 1

Only One Option Correct Type

Direction (Q. Nos. 1-5) This section contains 5 multiple choice questions. Each question has four choices (a), (b), (c) and (d), out of which ONLY ONE option is correct.

Q. 

What is the major alkene product in the following reaction?

Detailed Solution for Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 1

Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 2

Which of the following gives 1-butene as the major product most easily on heating with AgOH?

Detailed Solution for Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 2


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Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 3

1-butene would be formed most easily in the following reaction when X is

Detailed Solution for Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 3

Rate of reaction in E2 reaction depends on acidity of β—H as well as steric hindrance at β-carbon. When X is F, acidity is maximum and there is less steric hindrance at less substituted β-carbon.

Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 4

Consider the following reaction and the product formed.

Q. 

The most likely mechanism of the above reaction is

Detailed Solution for Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 4


Above equilibrium can explain the formation of given product, hence reaction must proceed by E1 cb mechanism

*Multiple options can be correct
Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 5

One or More than One Options Correct Type

Direction (Q. Nos. 6-8) This section contains 3 multiple choice questions. Each question has four choices (a), (b), (c) and (d), out of which ONE or MORE THAN ONE are correct.

Q. 

Which of the following gives methanol as the major product when heated with AgOH?

Detailed Solution for Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 5

All these lacks β—H undergo SN2 reaction giving methanol, b has β—H undergoes Hofmann’s elimination giving ethene.

*Multiple options can be correct
Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 6

Which of the following gives cis-2,3-diphenyl, 1-2-butene as the major E2 product, when treated with ethanolic KOH solution?

Detailed Solution for Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 6




*Multiple options can be correct
Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 7

The following elimination reaction, if proceeds by E1cb mechanism, equilibrium mixture would consist of

Detailed Solution for Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 7




Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 8

Comprehension Type

Direction (Q. Nos. 8-16) This section contains 2 paragraphs, each describing theory, experiments, data, etc. Nine questions related to the paragraphs have been given. Each question has only one correct answer among the four given options (a), (b), (c) and (d).

Passage I

The following E2 is carried out with different halogen substituent:

From the percentage yield of two products observed with different leaving group, it was concluded that both ease of leaving group and steric hindrance to the approach of base CH3O- to β-H affect the orientation of elimination reaction.

Q. 

Based to the above observation, which flask will have the largest amount of 1-hexene?

Detailed Solution for Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 8

Maximum elimination products would be formed in flask 1 and minimum elimination products would be formed in flask 4. Hence, even the 19% of total products in flask 1 would be much greater than 70% of total products in flask 4.

Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 9

Passage I

The following E2 is carried out with different halogen substituent:

From the percentage yield of two products observed with different leaving group, it was concluded that both ease of leaving group and steric hindrance to the approach of base CH3O- to β-H affect the orientation of elimination reaction.

Q. 

Highest percentage yield of 1-hexene in flask 4 leads us to conclude that

Detailed Solution for Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 9

Fluorine being the poorest leaving group, major product is one that is formed at fastest rate,

Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 10

Passage I

The following E2 is carried out with different halogen substituent:

From the percentage yield of two products observed with different leaving group, it was concluded that both ease of leaving group and steric hindrance to the approach of base CH3O- to β-H affect the orientation of elimination reaction.

Q. 

During formation of products in the given elimination reaction, the highest energy transition state would have been produced when methoxide ion reacts with

Detailed Solution for Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 10

Fluorine is poorest leaving group and formation of 2-hexene involve greater steric hindrance hence, highest energy transition state,

Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 11

Passage I

The following E2 is carried out with different halogen substituent:

From the percentage yield of two products observed with different leaving group, it was concluded that both ease of leaving group and steric hindrance to the approach of base CH3O- to β-H affect the orientation of elimination reaction.

Q. 

If we consider X to be iodine in the given elimination reaction, the number of different elimination products present in the flask-1 would be?

Detailed Solution for Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 11

Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 12

Passage I

The following E2 is carried out with different halogen substituent:

From the percentage yield of two products observed with different leaving group, it was concluded that both ease of leaving group and steric hindrance to the approach of base CH3O- to β-H affect the orientation of elimination reaction.

Q. 

Transition state with maximum double bond character will be formed when methoxide reacts with

Detailed Solution for Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 12

Iodine is best leaving group and 2-hexene is more substituted product, hence major product,

Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 13

Passage I

The following E2 is carried out with different halogen substituent:

From the percentage yield of two products observed with different leaving group, it was concluded that both ease of leaving group and steric hindrance to the approach of base CH3O- to β-H affect the orientation of elimination reaction.

Q. 

Transition state with least double bond character will be formed when methoxide reacts with

Detailed Solution for Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 13

 It forms the highest energy transition state.

Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 14

Passage II

When compound 1 is heated with C2H5ONa compound 2 and 3 are formed:


Two mechanisms were proposed for reaction I.
Mechanism A HBr is eliminated from compound 1 to form a symmetrical vinyl carbene intermediate A, which then rearranges to compound 2.

Mechanism B Ethoxide ion first abstract a proton to form a carbanion intermediate B which then rearranges with loss of bromide ion to form compound 2

To distinguish between the two machanisms, an isotopic labeling experiment was designed. Two compounds (Compound 4 and 5) were labelled with C-14 and each was treated separately with sodium ethoxide under identical experimental condition where following results were obtained.

 

Q. 

Based on the results of scheme 1, the chemist most likely ruled out mechanism A because they assumed that intermediate A should have formed

Detailed Solution for Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 14


Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 15

Passage II

When compound 1 is heated with C2H5ONa compound 2 and 3 are formed:


Two mechanisms were proposed for reaction I.
Mechanism A HBr is eliminated from compound 1 to form a symmetrical vinyl carbene intermediate A, which then rearranges to compound 2.

Mechanism B Ethoxide ion first abstract a proton to form a carbanion intermediate B which then rearranges with loss of bromide ion to form compound 2

To distinguish between the two machanisms, an isotopic labeling experiment was designed. Two compounds (Compound 4 and 5) were labelled with C-14 and each was treated separately with sodium ethoxide under identical experimental condition where following results were obtained.

 

Q. 

Compound 2 and 6 can be distinguished from each other by all of the following techniques except:

Detailed Solution for Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 15

2 and 6 are different compounds, can be separated by gas chromatography. They have different mass, can be distinguished by mass-spectrometry. 2 and 6 have different polarity, can be distinguished by dipole moment measurement. However both are achiral, cannot be distinguished by polarimetry.

Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 16

Passage II

When compound 1 is heated with C2H5ONa compound 2 and 3 are formed:


Two mechanisms were proposed for reaction I.
Mechanism A HBr is eliminated from compound 1 to form a symmetrical vinyl carbene intermediate A, which then rearranges to compound 2.

Mechanism B Ethoxide ion first abstract a proton to form a carbanion intermediate B which then rearranges with loss of bromide ion to form compound 2

To distinguish between the two machanisms, an isotopic labeling experiment was designed. Two compounds (Compound 4 and 5) were labelled with C-14 and each was treated separately with sodium ethoxide under identical experimental condition where following results were obtained.

 

Q. 

In reaction scheme 1, had the α-C to bromine be labelled with C-14

Detailed Solution for Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 16


Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 17

Matching List Type

Direction (Q. Nos. 18 and 19) Choices for the correct combination o f elements from Column I and Column II are given as options (a), (b), (c) and (d), out of which one is correct.

Q. 

Match the reaction from Column I with the type of m echanism from Column II and mark the correct option from the codes given below.

Detailed Solution for Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 17

(i) Given halide is a primary, predominantly undergo SN2 reaction.

(ii) Given halide is secondary, can undergo SN2 reaction. Also, E2 reaction leads to a conjugated system. Also it may react by E1 cb mechanism because it forms resonance stabilised carbanion.

(iii) It is a 3° halide and in the presence of weak base H2O, weak nucleophile H2O , it may undergo unimolecular substitution (SN1) and elimination (E1) reaction.

(iv) It may form a stable benzylic carbocation after hydride shift, hence may react by SN1 mechanism. Also it is a secondary halide, may undergo SN2 reaction. It may also react by E2 reaction ai it gives conjugated system. Carbanion. formed at β-C will be stabilised by resonance from ring, hence may undergo E1 cb mechanism.

Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 18

Match the alkyl halides in the Column I with the properties of their products produced in E2 elimination reaction in Column II and mark the correct option from the codes given below.

Detailed Solution for Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 18




*Answer can only contain numeric values
Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 19

One Integer Value Correct Type

Direction (Q. Nos. 20 and 21) This section contains 2 questions. When worked out will result in an integer from 0 to 9 (both inclusive).

Q. 

In the reaction given below how many elim ination products are formed in principle if reaction proceeds by E1 cb mechanism?


Detailed Solution for Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 19

*Answer can only contain numeric values
Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 20

Consider the following reaction,

Q. 

How many different stereoisomers of the major elimination product Y are possible?


Detailed Solution for Test: E2 Reaction Advanced, E1 Cb & Hofmann Elimination - Question 20

The major elimination product is

Since, the diene above is symmetrical, only three geometrical isomers exist.

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