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Question 1: Arrange the following in the increasing order of their acidic strength.

CH3COOH, FCH2COOH, Cl – CH2COOH BrCH2COOH, I – CH2–COOH

Solution:  Acidic strength increase with increase in strength of (–I) group hence, the correct order is

CH3COOH<ICH2COOH<BrCH2COOH<ClCH2COOH<F–CH2COOH

Question 2: Compare the acidic strength of the following.
CH3COOH , ClCH2COOH , Cl2HCCOOH, CCl3COOH

Increasing acidic strength due to increasing number of (–I) effect groups 

Question 3: Compare the basic strength of the following.

NH3, CH3NH2 (CH3)2NH (CF3)3N

Solution:  The increasing order of basic strength is as follows. 

\

CF3 group being – I effect groups attracts the electron pair of nitrogen makes protonation difficult in primary and secondary amine due to presence of +I effect group (CH3)  which make protonation easy. Hence the increasing order of basic strength is as follows.

Question 4: Explain why aniline is less basic than ammonia or aliphatic amines 

Solution: The lone pair present at the nitrogen in aniline is delocalised in the ring (by resonance) and hence, it is not free for protonation, while  in ammonia or aliphatic amines it is present at nitrogen all the time, hence it is readily available for protonation.

Question 5: Explain, why phenol is acid while aliphatic alcohols are not

Solution:  After loss of H+ ion from OH group of phenol the remaining part (Phenoxide ion) stabilizes by resonance, hence it will favour the loss of H+ ion and hence acidic in nature.

(No charge separation, more stabilization by Resonance) 

Question 6: Write the following Alkenes in increasing order of their stability  with explanation

R2C=CR2, R2C=CHR, R­2C=CH2, RCH=CH2, CH2=CH2

Solution:

From (a)  to (e) number of hyperconjugative structures increases, hence stability of alkene also increases, hence the correct order is

a <  b < c < d < e

You can also refer Organic Chemistry Revision NotesChemistry Syllabus and Best books of Organic Chemistry.

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