SI REVIEW HANDOUT ANSWERS

DISCLAIMER: I’ve been told to not go over problems 8 and 14 because they were a bit ahead of what was done in class. However, if you want to discuss what the potential solutions may be, I’m more than happy to discuss that in my sessions.I’m a student just like you, and sometimes I make mistakes. I apologize in advance if you notice some errors. Please let me know if there are any errors, so I can correct them in a timely manner. 1- a)

b) https://pubchem.ncbi.nlm.nih.gov/compound/R_-___-2-Chloropropionic-acid

c)

d)

2- Part I

Part II

3- Product C of Part I is a benzoic acid, and has a meta director on the ring which deactivates it, thus why it reacts slower than benzene in a substitution reaction.

4-a) Ortho and Para products

b)

1) 2) 3)

5-

a) From phenol

b) Starting w/ Acylation

Starting with Chlorination

NOTICE: You can start with either chlorination or acylation and it would yield the same final product, although starting with acylation yields a higher amount product and with less isomers. With Acylation we get ONE ortho isomer that we don’t need for the reaction, whereas when starting with chlorination, we get TWO isomers in solution that we don’t need for the reaction. Lastly, in the picture that says starting w/ Chlorination, notice that you can you either Br2 or NBS in presence of heat or light, use one on your reaction mechanism NOT BOTH!!!!!!!

6-META ATTACK

ORTHO ATTACK

PARA ATTACK

The substituent is an o,p director since the ortho and para attacks yield more stable intermediates.

7-

a) it represents one of the possible answers.

b)

9) Compound B (on the right) has the lower pKa, since the Cl is an electron withdrawing group, stabilizing the conjugate base. Compound B is therefor the strongest acid of the two, and has the weaker conjugate base.

10) False. Acyl chloride IS more reactive than a carboxylic acid when it comes to a nucleophilic acyl substitution, because chlorine is a better leaving group than an hydroxide.

11-

a) and b)

If DIBAL-H is used then the reduction reaction stops at product B.

12- The question was supposed to read: What amide(s) will form each of the following amines on treatment with LiAlH4

a) Two possible reactants

b)

13-

15-

16-