CHEM 2060

Exam #2

Study Guide

Chapter 5: Reactions of Alkenes and Alkynes

Know how the allylic carbocation allows for 1,2 and 1,4 addition products in

conjugated dienes (practice 5.33 pgs. 150-151).

Be able to give the products of oxidation of an alkene by hydroxylation with

KMnO4 and by ozonolysis with ozone then zinc and water (practice 5.37 and 5.38 pg.151).

Know that a terminal alkyne will react with sodium amide to form a carbanion (practice 5.40 pg.151).
 
 

Chapter 6: Aromatic Compounds

Know the material about benzene structure and bonding (Section 6.2 pgs. 154-157).

Know aromatic nomenclature including ortho, meta and para (like 6.21 and 6.23 (a and c) and 6.24 pg.182).

Know the electrophilic aromatic substitution reactions given in Fig. 6.2 pg. 166 and explained on pgs.168-172 (like 6.30 pg.183).

Be able to predict orientation of substitution (see Table 6.3 pg. 173) by knowing if a group is activating or

deactivating as well as if it is an ortho/para or meta director (like 6.15 pg.174, 6.30 pg.183, 6.31 and 6.33

pg.184, 6.42 pg. 185).
 
 

 Be able to carry out synthesis starting from benzene (like 6.37 pg. 184).

Know that 1° and 2° alkyl groups on benzene rings are oxidized to carboxylic acids by KMnO4 (like 6.34 pg.184).

Chapter 7: Stereochemistry

Determine the number of chiral carbons in a compound (like 7.4 pg. 192).

Determine which structures are identical or mirror images (like 7.8 pg. 195).

Be able to identify enantiomers, diastereomers and meso compounds (like 7.10 pg. 202).

Be able to assign a chiral carbon R or S configuration using the Cahn-Ingold-Prelog priority rules (like 7.26 pg. 215).

Chapter 8: Organic Halogen Compounds

Know IUPAC nomenclature (pgs. 220-221) (like 8.29 pg. 248).

Be able to draw structures given the name (like 8.30-8.31 pg. 248).

Know preparations (pg. 222).

Be able to fill in the box for starting material, reagent or product for nucleophilic substitution reactions

(like 8.3 pg. 226; 8.33 and 8.37 pgs. 248-249). Know different nucleophilic substitution mechanisms (SN1 and SN2) such as what type of nucleophile is used and what type of products (stereochemistry) are obtained (like 8.39 pg. 249). Know general characteristics of SN1 and SN2 mechanisms such as SN2 goes through a 5-membered transition state with 1° and 2° alkyl halides and SN1 goes through a carbocation intermediate with 3° and 2° alkyl halides

(pgs. 238-239).

 Know general characteristics of E1 and E2 mechanisms as with nucleophilic mechanisms above (remember Saytzeff's rule) (pgs. 241-243). Chapter 9: Alcohols, Phenols, and Ethers

Know IUPAC nomenclature (like 9.32, 9.34, 9.35 and 9.37 pgs. 287-288).

Know that alcohols have unusually high boiling points due to hydrogen bonding and as MW increases that

boiling point increases (like 9.40 pg. 288-289). Know preparations (pgs. 263-264).

Know how to arrange phenols by acidity (like 9.47 pg. 289).

Know reactions with the O-H bond in alcohols with Na and phenols with NaOH (like 9.48 and 9.49 a.

pgs. 289-290), SN1 and SN2 reactions with the C-O bond in alcohols and ethers (like 9.50 & 9.52 pg. 290),

dehydration of alcohols (Saytzeff's rule) (like 9.53 pg. 290), and oxidation of 1° alcohols to aldehydes (with

PCC) or to carboxylic acids (with CrO3 or Na2Cr2O7) and 2° alcohols to ketones (like 9.51 pg. 290).