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Test: General Organic Chemistry Level - 2


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30 Questions MCQ Test Chemistry for GRE Paper II | Test: General Organic Chemistry Level - 2

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Test: General Organic Chemistry Level - 2 - Question 1

Identify the correct acidic strength order in the following compounds.



Test: General Organic Chemistry Level - 2 - Question 2

Which of the following is most basic?

Test: General Organic Chemistry Level - 2 - Question 3

Which of the following is most basic?

Test: General Organic Chemistry Level - 2 - Question 4

The total number of cyclic isomers possible for a hydrocarbon with the molecular formula C4H6 is

Detailed Solution for Test: General Organic Chemistry Level - 2 - Question 4

5 cyclic isomers are possible for C4H6, possible.

Test: General Organic Chemistry Level - 2 - Question 5

The correct order of acidity of the following compound A-C is:

Detailed Solution for Test: General Organic Chemistry Level - 2 - Question 5

It follows huckels rule. in the 1st case if it loses H+ ion then it's conjugate base is stabilized by all the CF3 groups . in 3rd case conjugate base is stabilized by electron withdrawing double bonds.hence stable. in 2nd case it becomes antiaromatic.

Test: General Organic Chemistry Level - 2 - Question 6

The order of acidity of the protons H in each of the following is:



Detailed Solution for Test: General Organic Chemistry Level - 2 - Question 6

Aldehyde is more acidic then ester, as ther is +R effect of -OMe group in ester, it decreases the electron withdrawing power of carbonyl group.for second case it is ester.but for 3rd case, the (alfa H) is attached with two carbonyl group.
so the order of acidity is ¡>¡¡¡>¡¡

Test: General Organic Chemistry Level - 2 - Question 7

Imidazole has a pKa = 7 with respect to its conjugate acid. Which N is protonated in this conjugate acid and why?

Test: General Organic Chemistry Level - 2 - Question 8

When CH3Cl undergoes homolytic bond-fission:

Detailed Solution for Test: General Organic Chemistry Level - 2 - Question 8

Correct Answer :- c

Explanation :

 CH3Cl --------------> CH3 + Cl

Methyl free radical sp2 hybridized (with singly occupied p-orbital.

(sp3 hybridized carbon) tetrahedral bond angle 109o28

Test: General Organic Chemistry Level - 2 - Question 9

For the following compounds, which nitrogen has the least tendency to be protonated?

Detailed Solution for Test: General Organic Chemistry Level - 2 - Question 9

Test: General Organic Chemistry Level - 2 - Question 10

Increasing order of pKa values (pKa = –log Ka) of H2O, CH3OH and C6H5OH is:

Detailed Solution for Test: General Organic Chemistry Level - 2 - Question 10

The pKa of water is 14

The pKa of methanol (CH3OH) is 15.5

The pKa of Phenol (C6H5OH) is 9.88

Test: General Organic Chemistry Level - 2 - Question 11

The main sources of arenes among these are:

Detailed Solution for Test: General Organic Chemistry Level - 2 - Question 11

As these petroleum and natural gas comprise of naturally occurring compounds such as carbon and hydrogen in abundance, these serve as the main source of arenes.

Test: General Organic Chemistry Level - 2 - Question 12

Which of the following reaction undergoes in the forward direction:

Detailed Solution for Test: General Organic Chemistry Level - 2 - Question 12

Negative charge over S atom gets additional stability by conjugation through vacent 3d orbital of S ,so HS- is the most stable species and the reaction undergoes in the forward direction.

Test: General Organic Chemistry Level - 2 - Question 13

 Which among these is the simplest example for polycyclic arenes?

Detailed Solution for Test: General Organic Chemistry Level - 2 - Question 13

Naphthalene has fused ring of aromaticity and has the simplest structure when compared with other polycyclic aromatic hydrocarbons.

Test: General Organic Chemistry Level - 2 - Question 14

The compound that is anti-aromatic is:

Test: General Organic Chemistry Level - 2 - Question 15

The compound A is:

Test: General Organic Chemistry Level - 2 - Question 16

Which among these is not a representative arene compound?

Detailed Solution for Test: General Organic Chemistry Level - 2 - Question 16

Picric acid is a representative arene compound but not picric chloride.

Test: General Organic Chemistry Level - 2 - Question 17

 Identify the correct statement which is related to aromatic hydrocarbon

Detailed Solution for Test: General Organic Chemistry Level - 2 - Question 17

 An aromatic hydrocarbon always has a sigma as well as a delocalized pi bond found between the carbon atoms.

Test: General Organic Chemistry Level - 2 - Question 18

Arrange the following compounds in order of decreasing acidity: 

Detailed Solution for Test: General Organic Chemistry Level - 2 - Question 18

Electron donating groups increase the acidity of phenol when present as substituent on the benzene ring while electron withdrawing groups decrease the acidity of phenol.

Cl and NO2 are electron withdrawing groups while -CH3 and -OCH3 are electron donating groups.

However, nitro undergoes resonance also which allows it to better stabilize the negative charge of the oxygen as compare to chlorine and thus acidic character of nitro phenol would be higher than that of chloro phenol.

So, Nitrophenol is the most acidic compound here followed by chloro phenol.

Hence, the correct option is 2.

Test: General Organic Chemistry Level - 2 - Question 19

Arrange the following carbocation in increasing order of their stability:



Detailed Solution for Test: General Organic Chemistry Level - 2 - Question 19

F shows -I effect and hence it will decrease the stability of carbocation.
so it should be 2>3>1

Test: General Organic Chemistry Level - 2 - Question 20

How many compounds become aromatic after deprotonation?

Detailed Solution for Test: General Organic Chemistry Level - 2 - Question 20

Compound which gives an stable conjugate base deprotonation will deprotonate easily.

so, 1,3 and 6 will become aromatic after deprotonation.

Test: General Organic Chemistry Level - 2 - Question 21

Which of the following is anti-aromatic?

Test: General Organic Chemistry Level - 2 - Question 22

A compound given below shows a large dipole moment. Which of the following resonance structures can be used to adequately explain this observation?




Detailed Solution for Test: General Organic Chemistry Level - 2 - Question 22

Both aromatic rings are preferred. Therefore, D option is correct.

Test: General Organic Chemistry Level - 2 - Question 23

Among the following compounds, which is the correct order of % enol content?

Detailed Solution for Test: General Organic Chemistry Level - 2 - Question 23

In the 1st compound the double bond is at the bridgehead carbon , as a result this compound cannot exist in enol form because such conformation would give an impossibility strained ring .Such dis stabilizing effect is absent in 2 nd compound . Whereas the 3 rd compound exclusively exist in enol form due to the formation of intramolecular hydrogen bonding

According to britz's rule at bridge head position -ve charge is unstable so; 3>2>1

Test: General Organic Chemistry Level - 2 - Question 24

Which of the following compounds have higher enol content?

Detailed Solution for Test: General Organic Chemistry Level - 2 - Question 24

With electron withdrawing group, the keto-form dominates and with electron donating group, the enol form dominates. Since OCH3 is an electron donating group, (II) will have higher enol content.

Test: General Organic Chemistry Level - 2 - Question 25

Which of the following compounds have less enol content?

Detailed Solution for Test: General Organic Chemistry Level - 2 - Question 25

In the first compound after formation of enol the ring becomes aromatic (when the lonepair over N atom involve in conjugation) and this is a stabilizing factor but no such stabilizing factor is present in the enol form of 2. So 1 has higher enol content and 2 has lower enol content.

Test: General Organic Chemistry Level - 2 - Question 26

The order of number of enolizable protons in each of the following:

Test: General Organic Chemistry Level - 2 - Question 27

The amount of enol form present at equilibrium for each of the following is:

*Multiple options can be correct
Test: General Organic Chemistry Level - 2 - Question 28

Which is incorrect representation?

Test: General Organic Chemistry Level - 2 - Question 29

Arrange the following compounds in acidic order:




Detailed Solution for Test: General Organic Chemistry Level - 2 - Question 29

Correct Answer :- a

Halogen group have no mesomeric effect only inductive effect on benzene ring so correct answer is 2>3>4>1

Test: General Organic Chemistry Level - 2 - Question 30

Arrange the following compounds in order of Ca—Cb bond length:




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