Summary of CHEM 224 Final Exam, Spring 2022

NMR (28 pts)

1) Judges knowledge of where to expect different types of peaks in 1 H-NMR
(ranking 8 different protons from more downfield to more upfield)

Cyclopentane = 1.5 ppm (8)!!!!!! 2 CA's = 11.4 ppm (1)!!!!

Benzene = 7.3 ppm (2)!!!!! Ether = 3.3 ppm (5)!!!!!!!
Alkene = 5.4 ppm (3)!!!!!! Ketone = 2.1 ppm (6)!!!!!!!!
Alkyne = 1.9 ppm (7)!!!!!!! Ester = more downfield than ethers (4)!!!!!!

2) Match and assign 1 H-NMR peaks for 4 isomeric compounds

WHEN Cl IS PRIMARY:
WHEN Cl IS SECONDARY:

Structures, Nomenclature, and Properties (69 points)

3) Draw isomers of a given empirical formula with given functional groups.
4) Draw and name isomers of an aromatic compound with common names.

2,4,6-Trinitrotoluene
 3-nitroacetophenone

5) The common abbreviations or names for 8 compounds are given-draw structures.

NBS: N-bromosuccinimide

THF: Tetrahydrofuran

DMSO: Dimethylsulfoxide

DMS: Dimethyl sulfide

TEA: Triethylamine

DIBAL: Diisobutyl Aluminum Hydride

MCBPA: meta-chloroperoxybenzoic acid

6) Chemical names for 8 compounds given-draw structures.

7) Predict and explain the relative acidity of two compounds.

8) Concerns aromatic rings other than benzene

(Hückel's #)
Aromatic = 2, 6, 10, 14
Antiaromatic = 4, 8, 12, 16
Non Aromatic

NOTES:
(+) does not contribute as electrons
(-) contributes as electrons and count as pi electrons in aromatic compounds
Reactions (69 pts) All of these request the product, none requests the
reagent or starting material.
9-13) Various reactions that involve additions to alkenes
14-15) SN1 vs. SN2 reactions
16-17) Selectivity of hydride reducing agents
LAH
reduces everything

NaBH4
ketone
aldehydes

H2

18-19) Reactions of Grignard reagents

Protecting group via grignard rxn:

20) Diels-Alder reaction, regiochemistry, but no stereochemistry

21-22) Two different types of reactions of benzene rings

Para-Meta-Ortho directing
23-24) Two intramolecular reactions

Intramolecular Claisen condensation:

Intramolecular aldol condensation:

25-30) Reactions from Chapter 21 - one of them is a 4-step sequence

 When base is added:

Aldol addition reactions and Claisen condensation reactions both produce 1,3-
difunctionalized compounds:

Attacks at beta position:

Aldol condensation: alkene at alpha and beta position

Crossed aldol:

Reaction Characteristics and Mechanisms (40 pts)

"20" [31]) Simple mechanism under basic conditions
"31" [32]) Simple mechanism under acidic conditions