10/13/2017 Organic Chemistry II Lab Fall 2017 Synthesis of Aniline (part I & 2)

Question

10/13/2017 Organic Chemistry II Lab Fall 2017 Synthesis of Aniline (part I & 2) 1. Why must the solution be made alkaline (i.e. addition of NaOH) before steam distillation? 2. If NaOH (in question 1) was not added to the solution, and you then extracted with methylene chloride, what layer/phase would the product be found? Why? 3. a)Why is it necessary to use steam distillation instead of extraction? b) What is the issue encountered by use of steam distilation? 4. Why is it a better idea to use steam distillation rather than simple distillation in part I? 5. Why is tin (with hydrochloric acid) the most commonly used reducing agent?

Explanation / Answer

Q1

aniline is a base, therefore, we need basic media to avoid acid/base reaction

Q2

the organic layer --> will contain the aniline

aqueous layer --> contains the ionic species

We want to have the product in the organic layer

If we didnt add NAOH, then the product will be in the other phase

Q3

extraction can't be done, since aniline will not give a good "extraction" yield. that is, will have a KD value near to 1, which implies approx 50%-50% distribution

Q4

simple distillation will boil/burn the aniline, steam distillation is much gentler

Q5

tins is readily available and cheap.

IT is also a good donator of electrons, since it can form:

Sn(s) = Sn+2 + 2e-

Sn+2 = Sn+4 + 2e-

Related Questions

Navigate

• Browse (All)
• Browse 1
• Subjects

---

---

Integrity-first tutoring: explanations and feedback only — we do not complete graded work. Learn more.