CHEMISTRY 3222
FALL 2011
Lab Coordinator: Dr. Mary Bean, 118 Fleming, 713-743-2761
Your TA’s name:_______________________
Office:_______ Office hours:______________
For the laboratory you will need the following items:
1. The textbook: “Signature Lab Series: Chemistry 3221/3222”. This is a
custom manual published by Cengage Learning.
2. A laboratory notebook which is permanently bound, has serially numbered
pages, and which allows you to make a removable carbon copy which can be
turned in for grading.
3. A laboratory coat - long-sleeved and knee length
4. Sturdy, closed-toed shoes that cover the entire foot. No sandals are
allowed!!
5. Safety goggles (NOT SAFETY GLASSES). The laboratory coat and
goggles must be worn in the laboratory at all times anyone in the laboratory
is doing experimental work.
6. A STRONG, RELIABLE lock for your laboratory drawer. Lock your drawer
whenever you leave your bench, even if you are only walking across the
room! Lock your drawer at the end of every lab period. You are responsible
for any broken, missing, or stolen glassware and equipment.
NOTE: Few lab manuals are perfect! Sometimes adjustments in procedure need to be made for
the best results. The syllabus describes some of these changes, but additional changes may be
necessary. It is the responsibility of the student to make note of any such change when given by
the TA.
SPECIAL NOTE: For safety reasons, if you are more than 15 minutes late for the pre-lab lecture,
you may not perform the experiment.
Aug. 23-27
Orientation, check-in. Wash glassware and watch film on safety.
NMR lecture
Aug. 30-Sept.3 Remember to bring your lab coat, goggles, lab manual, lab
notebook (with sections I-V of the Laboratory Format Handout already
completed!), and lock. You will not be allowed to participate without the
proper shoes, labcoat and goggles.
Prelaboratory preparation: Review “Practicing Safety in the Laboratory,” pp. 1-12.
Review section 10-11, pp. 445-448 of Wade. Read “Borohydride Reduction of 9Fluorenone”, pp. 209-210 and “Carbocation Rearrangements –
Benzopinacolone” , pp. 215-216 of the lab manual.
Prelab Questions: Answer Exercise Questions 1 – 5 on pp 209-210 and Exercise
Questions 2, 4 and 5 (omit C13 NMR) on pp. 215-216. Also, propose a
mechanism for the benzopinacol – benzopinacolone rearrangement using
sulfuric acid as the catalyst.
EXPERIMENTAL: Both experiments are performed as written. An alternate heat
source may be used. There are no post-lab questions.
Sept. 6-10
Review Chapters 12 and 13 in Wade.
EXPERIMENT: Part 1: You will work the problems in a Spectroscopy Handout.
Some problems will be worked with the help of the TA, some will be worked in
groups, and some must be worked individually. These problems will be turned in
at the end of the lab period.
Part 2: You will learn to use the FT – IR and will be introduced to the NMR. One
IR spectrum will be turned in with the Spectroscopy Handout. One interpreted
NMR will be turned in on the regular due date.
Sept. 13-17
Review pp. 460-467 and 494-496 of chapter 11 in Wade.
SYNT 725: Oxidizing Methoxybenzyl Alcohol to Methoxybenzaldehyde Using
Phase-Transfer Catalysis, pp. 217-229. The microscale procedure will be
performed. TLC will be omitted. Prelab Questions: 1-5, pp.231-232. Postlab
Questions: 1-7, p. 230.
SYNT 726: Two Methods for the Synthesis of Phenacetin, pp. 233-245. Only the
semi-microscale Williamson Ether Synthesis will be performed today. The Amide
Synthesis will be performed later in the semester. Prelab Questions: 1-4, pp.
249-250. Postlab Questions: 1,2,4,5; p. 248.
Sept. 20-24
SYNT 717: The Diels-Alder Reaction of Anthracene with Maleic Anhydride, pp.
251-256. The semi-microscale procedure will be performed. Prelab Questons: 15, pp. 261-262. Postlab Questions: 1-5, p. 260.
Sept.27-Oct.1
Handout: The Friedel-Crafts Reaction: Preparation of p-Methoxybenzophenone.
Answer the questions given in the handout. (The Friedel-Crafts acylation of mxylene in the lab manual will not be performed.)
Oct. 4-8
REAC 716: Nitrating Acetanilide or Methyl Benzoate: Electrophilic Aromatic
Substitution, pp. 263-273. Both nitrations will be performed and the substitutions
will be compared. Prelab Questions:1-3, p. 273. Postlab Questions: 1-3, p. 271.
Oct. 11-15
MIDTERM EXAM
SYNT 721: Synthesis of Trans-9-(2-Phenylethenyl)Anthracene: A Wittig
Reaction, pp. 295-305. The microscale procedure will be performed. Prelab
Questions: 1-4, pp. 307-308. Postlab Questions: 1-4, p. 305.
Oct. 18-22
Qualitative Organic Analysis; Classification Tests: pp. 285-293. Omit Parts B, D,
and E.You will perform tests on known compounds and an unknown. Your
unknown must be identified as a primary, secondary, or tertiary alcohol, an
aldehyde, a ketone or a methyl ketone,
Answer Exercise questions 1-5 as post-lab questions.
Oct. 25-29
SYNT 713: Preparing Isopentyl Acetate by the Fischer Esterification, pp. 312327. The semi-microscale procedure will be performed. Prelab Questions: 1-4,
pp. 329-330. Postlab Questions: 1, 2, 5,6; p. 328.
SYNT 726: Two Methods for the Synthesis of Phenacetin, The Amide Method,
pp. 243-248. The semi-microscale procedure will be performed. Prelab Question
5, p. 250. Postlab Questions: 1, 2, p. 248.
Nov. 1-5
SYNT 754: A Multistep Synthesis Sequence: An Aldol Condensation, A Michael
Addition, and Ethylene Ketal Formation, pp. 331-350. Only the Aldol
Condensation and Michael Addition will be performed. The semi-microscale
procedures will be performed. Prelab Questions: 1, 3, 4; pp 349-350.
Postlab Questions: 1, 2, 5; pp. 347-348.
Nov. 8-12
m-Aminoacetophenone; Selective Reduction of Nitro, pp. 309-311. Answer
Exercise Questions 1-4 as postlab questions.
Properties of Amines, pp 351-354. Omit Part C. Prelab Questions 1, 3, 5; p. 354
Postlab Questions: 1, 4; p. 354.
Important Note: Wash all glassware and make sure that all of the necessary
equipment is in your drawer for check-out next week. It is your responsibility to
replace anything broken during the semester.
Nov. 15-19
Final Exam (Cumulative) and Check-out.