[PDF] [PDF] Nucleophilic Substitution Reactions - Laney College

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ORGANIC CHEMISTRY LANEY COLLEGE

CHEM 12A INSTRUCTOR: Wm. Trego

Nucleophilic Substitution Reactions: Competing Nucleophiles Reading Experiments 22, 22A, 22B and 22C (Gas Chromatography) in Pavia (5 th edition). Read all of the

Required Reading See also Chapter

7 , Sections 7.4 and 7.5, in Klein for in-depth discussion on substitution reactions.

General

Nucleophilic substitution reactions usually proceed with either first order (SN

1) or second order (S

N

2) kinetics.

You will

investigate these two types of substitution reactions: One that utilizes a primary or secondary and one

that util

izes a tertiary electrophilic substrate (R-LG, where LG is a leaving group). One goal of the experiment

is to determine the affect of the nucleophile (Nu:) on the rate of reaction and another is to determine whether chloride (Cl ) or bromide (Br ) is a stronger nucleophile.

Procedure

(with modifications)

The textbook procedure for

Experiment 22 describes the preparation of a "nucleophilic mixture" which is used for both 2 2

A and 2

2 B. The nucleophilic mixture will be prepared by the instructor ahead of time. This mixture

will be used in both experiment 22A (1-butanol, or 2-butanol) and 22B (t-butyl alcohol). Since the mixture will

contain concentrated sulfuric acid (H2 SO 4 ), which is extremely corrosive, use gloves at all time during the

laboratory. For experiment 22A, use the apparatus shown on the attached page (which is similar to what is

shown on p. 194), but with the minor modification to the gas trap shown in the lab lecture. For experiment 22B

use the provided screw-capped vial, instead of a centrifuge tube.

Prelab

Include:

Name, Date, Title, Objective, Reaction Equations, Reagent Table, and an Outline of the procedure from the text It is crucial that you understand the procedure for each reaction in experiments 22A and 22B and the isolation procedure given in the text for each case. The more time it takes for you to isolate the product

alkyl halides the greater the chance of losing product to decomposition, especially for Part 22B, which

consequently can adversely affect your analysis of the product. In your Reagent Table, show the amounts and

mmoles of the components of the "Nucleophilic Mixture" (the ammonium halides), but note that you will use be

using measured portions of a previously prepared mixture, 10.0 mL for experiment 22A and 6.0 mL for experiment 22B (6 mL). Calculate and show the number of mmoles of ammonium bromide and ammonium

chloride that are used for each experiment (use d = 1.4 g/mL for the nucleophilic mixture). See the top of p.

193 for the amo

unts of all components used in the nucleophilic mixture.

Include a Separation Scheme for each

part of the experiment, 22A and 22B. The beginning of your separation scheme should be the point when the

reaction is complete (i.e., the mixture of alkyl halides, plus the remains of the nucleophilic mixture). Consider

all of the possible materials that should make up the mixture before you show the separation of anything (in

your scheme). Nu R-Nu k R ate = k[R-LG][Nu] for S N 2

Rate = k[R-LG] for S

N 1

R-LGLG:

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ORGANIC CHEMISTRY LANEY COLLEGE

CHEM 12A INSTRUCTOR: Wm. Trego

Analysis of Product Mix

tures

Analyze the product mixtures from experiment 22A and 22B by gas chromatography (GC). Find the percent

composition for each alkyl halide. Use the provided chromatograms of the 1:1 mol/mol mixture of halides to

calculate response factors for each alkyl halide, correct the peak areas from your chromatograms, and find the

percent composition for your halide mixture. To determine which peak represents which product, assume that

bp is the dominant factor, i.e., lower bp means first off the column. Also note that the GC chromatogram of

your sample from Experiment 22A should contain a third peak (why?), which you should identify then ignore

with regard to the integration of peak areas.

To Complete the Experiment

Full Report

Additional Guidelines for the full report will be provided.

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