A compound X undergoes the following reactions:X NaOH(aq)/heat > C4H10O Cr2O7(2-), H+(aq)/ heat> C4H8O.What is X?
Correct answer: B. 2 - Bromobutane
- A. 1 - Bromobutane
- B. 2 - Bromobutane
- C. 1-Bromo-2-Methylpropane
- D. 2 - Bromo - 2 - Methylpropane
Explanation
C4H8O having one oxygen rules out the possibility of the intermediate compound being a primary alcohol as if it were to be a primary alcohol, a carboxylic acid would have been formed having 2 oxygen atoms in the molecule and not one. Thus, we can infer that the intermediate alcohol is a secondary alcohol and C4H8O is a ketone leading us to conclude that Bromine must have been on either carbon 2 or 3. Also, we must not have a side chain as it would either give us a tertiary alcohol with 10 hydrogens which wouldn't had oxidized further or a primary alcohol which would have oxidized to give a carboxylic acid. Both are not required so, based on the options provided we can choose B as the answer since it has no side chain and the bromine is not on the end carbons.
Last updated
About Nucleophilic Substitution
Nucleophilic substitution replaces a leaving group in an alkyl halide when an electron-rich nucleophile attacks the carbon atom. The topic compares SN1 and SN2 mechanisms, including reaction conditions, substrate structure, solvent effects, nucleophile strength, carbocation formation and stereochemical changes, and distinguishes substitution from elimination.
Practise Alkyl Halides
458 free Alkyl Halides MCQs from Chemistry, each with the correct answer and an explanation. Unlimited attempts, no account needed.
Exams that ask Chemistry questions like this
Chemistry is on 12 papers prepared for on TestUstad, and all of them draw the same bank, so this question is worth knowing for every one of them.
Related questions
50% inversion of configuration of molecules take place in a___________________?
A Grignard reagent is formed when an alkyl halide reacts with
A tertiary alkyl halide usually undergoes nucleophilic substitution by the SN1 mechanism because
Alkyl halides are considered to be very reactive compounds towards nucleophile because_________________?
Alkyl Halides involving -C-X bond breakage and- C-Nu bond formation simultaneously.