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Only One Option Correct Type
Direction (Q. Nos. 1-10) This section contains 10 multiple choice questions. Each question has four choices (a), (b), (c) and (d), out of which ONLY ONE is correct.
Q.
Arrange the following in the increasing order of reactivity with NH3.
I. CH2O
II. CH3CHO
III. CH3—CO—CH3
This is because of steric hindrance because NH3 attack carbonyl carbon as nucleophile (Sn2) and then steric hindrance is the main factor.
The major organic product formed in the following reaction is
Which carbonyl compound below gives the reddish orange precipitate with 2, 4-dinitrophenyl hydrazine?
Conjugated aldehydes and ketones give reddish orange precipitate with 2,4-dinitrophenyl hydrazine. Non-conjugated aldehydes and ketones give orange precipitate in the same reaction.
Which carbonyl compound below forms a single semicarbazone when allowed to react with semicarbazide?
It is symmetrical ketone, forms single semicarbazone with semicarbazide. All others are unsymmetrical, forms more than one stereoisomers of semicarbazones in the same reaction.
A hydrocarbon X (C7H14) on ozonolysis followed by work-up with Zn- H2O gives C6H12O as one of the product which on subsequent treatment with KOH/I2 gives yellow precipitate and salt of a chiral acid. Hence, X could be
Ozonolysis of X gives C6H12O which has one carbon less than X. Hence, X must contain double bond at terminal carbon.
Which gives more than one oximes on treatment with hydroxylamine?
It is unsymmetrical aldehyde, forms syn and anti oximes with hydroxylamine. All others are symmetrical, forms single oxime
Which forms an unsaturated amine on treatment with cyclopentanone in slightly acidic medium?
Secondary amine forms enamine with aldehydes or ketones.
Consider the following reaction,
Q.
X (major) in the above reaction is
What is the final major product Y in the following reaction?
What is the final major product in the following reaction?
One or More than One Options Correct Type
Direction (Q. Nos. 11-14) This section contains 4 multiple choice questions. Each question has four choices (a), (b), (c) and (d), out of which ONE or MORE THAN ONE are correct.
Q.
What is/are expected product(s) in the following reaction?
Which of the following form enamine on heating with a secondary amine in weakly acidic medium ?
Aldehydes and ketones containing α-H form enamines when treated with secondary amine in slightly acidic medium.
The compound(s) which form a pair of diastereomers with hydroxylamine is/are
All of these form more than one oxim es with H2N—OH
The compound(s) below that gives yellow precipitate with KOH/I2 is/are
Aldehydes and ketones with groups form iodoform with NaOH/I2. Besides, aldehydes and ketones, alcohols with
group also form iodofom in the same reaction.
Comprehension Type
Direction (Q. Nos. 15-17) This section contains a paragraph, describing theory, experiments, data, etc. Three questions related to the paragraph have been given. Each question has only one correct answer among the four given options (a), (b), (c) and (d).
Passage
Aidehydes and ketones react with ammonia and primary amines to form imines in slightly acidic condition. A typical reaction mechanism with a primary amine is as follows
The proper pH control is crucial to imine formation otherwise reaction does not proceed at appreciable rate.
However, if a secondary amine is reacted, no hydrogen is left on nitrogen on intermediate (I) for the deprotonation in step II. Hence, the reaction proceeds as
Enamine is a suitable intermediate route for α-alkyiation of a carbonyl compound.
Q.
What happens if imine form ation is carried out at very low pH?
At very low pH (highly acidic condition), amines get protonated and its nucleophilic character is lost.
Aidehydes and ketones react with ammonia and primary amines to form imines in slightly acidic condition. A typical reaction mechanism with a primary amine is as follows
The proper pH control is crucial to imine formation otherwise reaction does not proceed at appreciable rate.
However, if a secondary amine is reacted, no hydrogen is left on nitrogen on intermediate (I) for the deprotonation in step II. Hence, the reaction proceeds as
Enamine is a suitable intermediate route for α-alkyiation of a carbonyl compound.
Q.
Which of the following is expected to give more than one imine when treated with CH3NH2?
Aidehydes and ketones react with ammonia and primary amines to form imines in slightly acidic condition. A typical reaction mechanism with a primary amine is as follows
The proper pH control is crucial to imine formation otherwise reaction does not proceed at appreciable rate.
However, if a secondary amine is reacted, no hydrogen is left on nitrogen on intermediate (I) for the deprotonation in step II. Hence, the reaction proceeds as
Enamine is a suitable intermediate route for α-alkyiation of a carbonyl compound.
Q.
What is the product X in the following reaction?
One Integer Value Correct Type
Direction (Q. Nos. 18-21) This section contains 4 questions. When worked out will result in an integer from 0 to 9 (both inclusive).
Q.
In the following reaction, how many isomers of trioximes are formed?
Six isomers (stereoisomers) are possible for X.
Consider the isomeric aldehydes with molar mass 100, if all the isomers (only structural) are treated independently with NH2OH, how many of them would give more than two stereomeric oximes?
MW = 100 indicates that molecular formula of aldehyde is C6H12O . For obtain ing more than two oximes, aldehyde must exist stereomeric.
All the above has one chiral carbon each. Hence, when reacted with H2NOH, forms more than two oximes.
When formaldehyde reacts with ammonia, a typical compound called hexamethylene tetramine is formed. How many six membered rings are present in this compound?
The smallest acyclic ketone that gives pair of diastereomers with CH3NH2 in slightly acidic medium has how many carbon atoms?
The ketone must contain a chiral carbon.
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