This is the worksheet I created for my study group in preparation for their first midterm (Summer 2016).

1. Shashank Patil
Chem 3B Study Group
OH: MW 1-1 PM
shashankpatil@berkeley.edu
July 6, 2016
Worksheet 4: MT 1 Review
1. Nomenclature: Provide a systematic name for the following compounds. Use common
nomenclature (ortho, meta, para) for any branched substituents.
2. Allylic Systems Circle the allylic carbons and write down the number of allylic
hydrogens
3. Bromination using NBS: Show all monobromination products
4. A The Diels Alder reaction is favorable. Explain why.
heat
+

2. B. Diels Alder involving heteroatoms can also occur. Predict the products of the reaction.
5. Hybridizations in cyclic systems + Aromaticity: Each of the hetero-cycles below are
aromatic. Clearly indicate which atomic orbital (p, sp2, sp, etc.) each lone pair resides in.
6. Electrophilic Aromatic Substitution (EAS)
A. What are the 3 fundamental steps in ALL EAS reactions?
1.
2.
3.
B.
7. Substituted Benzenes/Directing Groups

3. 8. Conceptual: Rxn A undergoes an EAS reaction to yield the following product. Reaction B is
very similar to A, but is unfavorable. Explain.
8. SNAR: Predict the Products/Mechanism
9. Final Pointers!
 SNAR (Nucleophilic Aromatic Substitution or NAS)
o Remember that you need an Electron Withdrawing Group (“electron sink”) at
the __________ or __________ positions in order for this reaction to occur.
o This reaction typical occurs in 2 steps
 1. Addition of Strong Nucleophile (Rate determining step: dependent
on the electrophilicity of C)
 2. Leaving Group leaves by pushing electrons down from EWG.
 Be very comfortable interconverting between different substituted benzenes using
your diazzonium ion.
 Be very comfortable understanding when to draw and when not to draw a Frost
(Polygon Method)diagram.
o Sol: When cyclic, planar, & completely conjugated.
 Remember stereochemistry in your products & remember to compare all your
products to check for repeats.
 Relax on the test. You will do great!
 Good luck 