Question

**ochem help please

Final Exam Questions, Experiment 5 A multistep synthesis of aniline from toluene is shown below, with reagents missing. Use it to answer the following questions. 1) Which reagents would you use to perform reaction A? a) KMnO b) N-bromosuccinimide, UV light. c) NaOH. d) OsO.. 2) Which reagents would you use to perform reaction B? a) PBr. b) p-toluenesulfonyl chloride. c) SOCI2. d) NaOCl, NaOH. 3) Which reagents would you use to perform reaction D? a) NaN3, heat. b) NH3. c) KOH d) Brz, KOH. 4) You're performing your Hofmann rearrangement, and you misplace your bottle of bleach. What could you use as a substitute that would still give good yield? a) Sodium azide. b) NaOH. c) Bromine. d) Hydrogen peroxide. 5) Why did you add NaHSO, at the end of your Hofmann rearrangement? a) To make the reaction mixture aqueous, not organic. b) To neutralize the acidic solution before extraction of product. c) To neutralize the basic solution before extraction of product. d) To destroy any leftover bleach in the reaction. 6) The NMR spectrum of 3-nitroaniline was taken in deuterated dimethylsulfoxide (DMSO), not CDCiz. Why? a) The residual CHCI peak would get in the way of the aromatic peaks in the product. b) 3-Nitroaniline is not soluble in CDCls. c) DMSO allows visualization of the peaks for the NH2 group. d) 3-Nitrobenzamide is not soluble in CDC13.

Answer 1

Kmnou by sock one or more or lesso, columns Column is use kinnoy in acidic medium 2 & Bralkoth with (1) The reagent used to perform osion- A reaction A n kinnou (option-A) This ģ because kinnon in acidic a strong oxidising agent that can oxidise any alky group present in the benzene sing conta at least one 2-4 atom (2) The reagent soch is used to perform reaction & option Leythors soch utselt het ③ The reagent used to perform reaction - D7 B82, ROH . ENEL Bralkohe 5 14 Ho | KBb + a (Hofmann ; option bromamide aniline browreaction , sake, B2, cotia (S 145 Instead of bleach, we can take B2, egant that could still give good field in Hofmann. rearrangement Bleach contain Naod, which have same benction as B21 Nooth Craobs NaBr) we add Narts at the end of Hofmann reagent option because to destory any leftover bleach 2 in the reaction. Na41503 + Nao Nagoy the the (6) The NMR-spectrum (bleach nifrvaniline was taken. of 3- ņ deuterated dimethm sulfoxide (Dinso) not CD Cd 3 because the residual Chol Peak would get in the way of the aromatic peaks in the product.