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4. Which product (or products) would you expect to obtain from each of the following reactions? In each part give the mechanism (SN1, SN2, E1, or E2) by which each product is formed and predict the relative amount of each product (i.e., would the product be the only product, the major product, a minor product, etc.?). (a) [structure] Br ---EtO- / EtOH, 50 °C---> (b) [structure] Br ---t-BuOK / t-BuOH, 50 °C---> (c) [structure] Br ---MeO- / MeOH, 50 °C---> (d) [structure] Br ---t-BuOK / t-BuOH, 50 °C---> (e) t-Bu [structure] Cl ---I- / acetone, 50 °C---> (f) t-Bu [structure] Cl ---MeOH, 25 °C---> (g) 3-Chloropentane ---MeO- / MeOH, 50 °C---> (h) 3-Chloropentane ---CH3CO2- / CH3CO2H, 50 °C---> (i) (R)-2-bromobutane ---HO- / 25 °C---> (j) (S)-3-Bromo-3-methylhexane ---25 °C / MeOH---> (k) (S)-2-Bromooctane ---I- / MeOH, 50 °C--->

          4.
Which product (or products) would you expect to obtain from each of the following reactions? In each part give the mechanism
(SN1, SN2, E1, or E2) by which each product is formed and predict the relative amount of each product (i.e., would the product be the
only product, the major product, a minor product, etc.?).

(a) [structure] Br ---EtO- / EtOH, 50 °C--->
(b) [structure] Br ---t-BuOK / t-BuOH, 50 °C--->
(c) [structure] Br ---MeO- / MeOH, 50 °C--->
(d) [structure] Br ---t-BuOK / t-BuOH, 50 °C--->
(e) t-Bu [structure] Cl ---I- / acetone, 50 °C--->
(f) t-Bu [structure] Cl ---MeOH, 25 °C--->
(g) 3-Chloropentane ---MeO- / MeOH, 50 °C--->
(h) 3-Chloropentane ---CH3CO2- / CH3CO2H, 50 °C--->
(i) (R)-2-bromobutane ---HO- / 25 °C--->
(j) (S)-3-Bromo-3-methylhexane ---25 °C / MeOH--->
(k) (S)-2-Bromooctane ---I- / MeOH, 50 °C--->

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4.
Which product (or products) would you expect to obtain from each of the following reactions? In each part give the mechanism
(SN1, SN2, E1, or E2) by which each product is formed and predict the relative amount of each product (i.e., would the product be the
only product, the major product, a minor product, etc.?).

(a) [structure] Br —EtO- / EtOH, 50 °C—>
(b) [structure] Br —t-BuOK / t-BuOH, 50 °C—>
(c) [structure] Br —MeO- / MeOH, 50 °C—>
(d) [structure] Br —t-BuOK / t-BuOH, 50 °C—>
(e) t-Bu [structure] Cl —I- / acetone, 50 °C—>
(f) t-Bu [structure] Cl —MeOH, 25 °C—>
(g) 3-Chloropentane —MeO- / MeOH, 50 °C—>
(h) 3-Chloropentane —CH3CO2- / CH3CO2H, 50 °C—>
(i) (R)-2-bromobutane —HO- / 25 °C—>
(j) (S)-3-Bromo-3-methylhexane —25 °C / MeOH—>
(k) (S)-2-Bromooctane —I- / MeOH, 50 °C—>

Added by Fernando D.

Chemistry: Structure and Properties

Nivaldo Tro 2nd Edition

Instant Answer

Solved by Expert George Bennett

04/06/2024

Step 1

g., reactions (c), (d), (e), (f), (g), (i), and (j) as written do not represent typical organic reactions). However, I will address the reactions that do make sense and provide a step-by-step solution for those. (a) EO + BuOH → EOH + BuO Show more…

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Which product (or products) would you expect to obtain from each of the following reactions? In each part, give the mechanism (SN1, SN2, E1, or E2) by which each product is formed and predict the relative amount of each product (i.e., would the product be the only product, the major product, minor product, etc.):

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00:01 To predict the products and mechanisms of these reactions, we need to evaluate the reagent in terms of its strength as a nucleophile, its strength as a base, and we need to note the kind of leaving group that we have.

00:18 So in the first example, we have a primary leaving group with a strong nucleophile, strong base.

00:25 So this is probably some combination of e2 and sn2.

00:34 And given that it's at 50 degrees celsius, we might expect a little more e2, but it's a primary leaving group, which might lead us to expect more sn2 products.

00:58 So the substitution product would be an ether, and the elimination product would be an alkene.

01:11 And given that it's a primary leaving group, say sn2 is probably major, and b2 product is probably minor.

01:25 Now, in the second example, we have a strong base that's not nucleophilic.

01:32 It's sterically hindered and we have a primary leaving group so the e2 product will be the only product of that reaction.

01:47 Third example we have a tertiary leaving group with a strong nucleophile strong base.

01:56 So it's probably e2 only.

02:12 We can't really get much sn2 from that because it's a tertiary leaving group.

02:22 And under the reaction conditions, it's not likely to undergo any sn1 substitution.

02:32 Next example, again, we have a sterically hindered non -nucleophilic base.

02:37 So that will be e2 for sure and give us the isobutene product.

02:53 Now in the next example, we have a secondary leaving group and we have a strong nucleophile weak base.

03:01 So this is going to be almost exclusively sn2.

03:11 And sn2 gives inversion of stereochemistry...

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