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CHEMISTRY 3221

Spring 2012

Lab Coordinator: Dr. Mary Bean, 318 STL, 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 that is permanently bound, has serially
numbered pages, and that 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 or shoes that leave a large area of the foot exposed
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 most 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 to
prelab lecture or you completely miss a shorter lecture, you may not perform
the experiment. Please ask the lab coordinator if a make-up lab is possible.

Jan. 17-23 Orientation, check-in. Wash glassware and watch films on safety
and using standard equipment.

Jan. 24-30 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: Read pages 1 – 30 and 45 – 54 of the


lab text. You may disregard the microscale distillation procedures
of TECH 0704. Answer in your laboratory notebook the Safety
Quiz on pages 11 – 12 and the Prelab Questions 1, 2a, 2b, 3 -5, pp.
67 - 68.

EXPERIMENT:

TECH 0704, Distillation, macroscale technique only, simple and


fractional: Substitute a mixture of 25 mL ethanol and 25 mL
water for the toluene/cyclohexane mixture. Record the
temperature at 2 mL intervals of distillate. Use glass beads to
pack the fractionating column.
Construct a graph of temperature vs volume for each distillation
in your lab notebook. Compare the efficiencies of the two
distillation methods in your lab notebook.

Postlab questions: 1,3 on p. 65.

Jan. 31-Feb. 6 Prelaboratory preparation:


Read TECH 0701, Measuring Melting points, pp. 31-44. You may
disregard the procedure described in Part 2. Answer in you
laboratory notebook Prelaboratory questions 1-4, pp. 43-44.

Read TECH 0703, Recrystallization, pp 69-82. Answer in your


laboratory notebook Prelaboratory questions 1-4, pp. 81-82.

EXPERIMENTS:

TECH 0701, Melting points


Part 1: You will use benzoic acid only.
Part 2: omit (You are responsible for the concept.)
Part 3: Perform as written. The possible unknown compounds will
be written on the board.

TECH 0703, Recrystallization: Perform as written. The starting


amount of acetanilide may be changed.
Note Carefully: Retain the products of all experiments until you
are given instructions about what to do with them. In this case,
retain the recrystallized acetanilide for determination of its
melting point after it is completely dry (one week).
Additional notes:
In an experimental procedure, the specification of a quantity as,
for example, “60 mg of benzoic acid” does not mean precisely 60
mg, but rather about 60 mg weighed to the precision of the
balance. Always record the actual mass weighed for use
(example 59.51 mg), not the mass specified in the procedure (60
mg). To insure reproducibility in weighing, always use the same
balance when you tare the container and later when you weigh
the container plus the recrystallized material.
Postlab questions: 4-6, p. 41 and 1- 3, p. 79.

Feb. 7-13 Prelab preparation: Read TECH 0707, Thin Layer Chromatography,
pp. 99-108; TECH 0708, Column Chromatography, pp. 82-90
Prelab questions: 1-3, pp. 111-112 and 1-5, p. 97.

Experiments:
TECH 0707: Part 1: Omit (Microliter pipets will be provided.)
Part 2: omit dichloromethane and methanol
Part 3: Only 3 slides are necessary.
NOTE: Sketch each TLC plate in your notebook. All TLC plates
must be turned in with the lab report. Place them in a sealed
envelope and staple it to your lab report. An evaluation of these
plates for appropriate sample application and concentration,
proper marking of developed spots, and correct Rf values will
contribute to the grade.

TECH 0708: Be prepared to perform the dry pack method. Your TA


will give you additional instructions.
Postlab questions: 2-4, p. 95 and 1-4, p. 109.

Feb. 14-20 Prelab preparation: Read TECH 0705, Extraction, pp. 129-135,
139-143

Prelab questions: 1-4, pp. 147-148.


Experiment: You will perform the macroscale procedure only.
Note Carefully: In this and all subsequent experiments, ether is
to be removed by rotary evaporator, not by evaporation into the
atmosphere. The TA will demonstrate the use of this instrument.

Important addition: After isolation, the purity of each compound


will be checked by melting point and TLC. Consider the evidence
provided by MP and TLC and comment on the efficiency of each
step of the extraction in your lab report.

Postlab questions: 1-6, p. 145.

Feb. 21-27 Prelab preparation: Read TECH 0722 (Steam Distillation), pp. 149-
155.
Prelab questions: 1-3, p. 169.
Experiment: The semi-microscale procedure will be performed.

Note the following changes: 10 g of ground cloves and a 500 mL


round-bottom flask will be used. Collect at least 100 mL of
distillate. Ether, not methylene chloride, will be used to extract
the clove oil (eugenol). With this change the organic layer is the
top layer, and the aqueous layer is the bottom layer. The ether is
removed by rotary evaporator as described earlier.
The experiments described in the section “Characterizing the
Product” will be omitted. A handout describing the conversion of
eugenol to a derivative will be provided.

Feb. 28-Mar. 5 Finish steam distillation. Post lab question #1, p. 167
should be included in the Calculations and Results sections of
your lab report.

Prelab preparation: Read Properties of Hydrocarbons, pp. 171-172


and TECH 0709, Gas Chromatography, pp. 113-124.
Prelab questions: 1-5, pp. 173 and 1-3, pp.127-128.

Experiments:
Properties of Hydrocarbons: Perform as written. Omit part C.
Gas Chromatography: A mixture of alkanes will be substituted for
the mixture esters on pp. 123-124.
Postlab questions: 1-6, pp. 172-173 and 3-4, p.125.

Mar. 6-10,19 MIDTERM EXAM

Prelab preparation: Read Nucleophilic Substitution of Alkyl


Halides, pp. 175-177.
Prelab questions: 1, 2, 4, p 180.

Experiment: Part A – Perform as written except substitute


bromobenzene for crotyl chloride.
Postlab questions: 1 and 2, p. 180.

Mar. 20-26 Prelab preparation: Handout: SYNT 719, Brominating Alkenes


Prelab questions: 1-4, p. 119.
Experiments: Cis-stilbene and trans-stilbene will be brominated
using microscale techniques.
Postlab questions: 1-4, p. 118.

Mar. 27-Apr. 2 Prelab preparation: Read Dehydration of Alcohols, pp. 185-


189.
Prelab questions: 1 – 5, pp. 188-189.

Experiment: Part B. will be performed as written.

The bromine test on p. 172, Part D. will be used to characterize


the product. GC will be used to determine the ratio of products
produced.

Postlab questions (Questons): 1-6, p. 188.


IMPORTANT NOTE: Wash all glassware needed for next week’s
experiment before you leave the lab. Do not wait until next week!

Apr. 3-9 Read the introduction to Triphenycarbinol on pp. 191-192 of the


lab manual and the related lecture text material: Wade, pp. 437-
449. The experimental procedure will be provided in a handout.

Answer the questions in the handout.

Note: The key to success in this reaction is a dry environment!


Carefully dry all
glassware as described by the TA. Immediately replace the caps
on all reagents used, especially the ether.

Apr. 10-16 Finish Grignard Reaction

Read ANAL 0729, Identifying an Unknown Alcohol , pp. 197-203.


Prelab questions: 1-6, pp. 207-208.

Experiments: Parts 1-4, pp. 201-203.


Postlab questions: 1-5, p. 205.

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.

Apr. 17-23 Final Exam (Cumulative) and Check-out.