For 10.29, the trans product (major product) and the cis product (third product) are displayed as possible E2 products. However, for 10.30, only the trans product (major product) is shown. How come the cis product is not needed?

Organic Chemistry: A Guided Inquiry
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Author:Andrei Straumanis
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Chapter9: Addition Via Cyclic Intermediate
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For 10.29, the trans product (major product) and the cis product (third product) are displayed as possible E2 products.

However, for 10.30, only the trans product (major product) is shown. How come the cis product is not needed?

10.29 We begin by analyzing the reagent. Ethoxide is both a strong nucleophile and a strong base. Next, we look at the substrate, which
e secondary. When a secondary substrate is treated with a reagent that is both a strong nucleophile and a strong base, we expect E2 and
S 2 products, with the E2 pathway providing the major product. The major product is the trans disubstituted alkene (the Zaitsev product).
Minor products include the SN2 product, the cis-disubstituted alkene, and the Hofmann product, as shown here:
Br
OEt
NaOEt
Major product
Minor product
Minor product
Minor product
10.30 We begin by analyzing the reagent. Hydroxide is both a strong nucleophile and a strong base. Next, we look at the substrate,
which is secondary. When a secondary substrate is treated with a reagent that is both a strong nucleophile and a strong base, we expect E2
and S2 products, with E2 giving the major product. The major product is the trisubstituted alkene (the Zaitsev product). Minor products
include the Hofmann elimination product and the S 2 product, as shown below. Notice the configuration of the double bond in the major
product. This configuration is dictated by the requirement that the beta proton and the leaving group be antiperiplanar in order for an E2
reaction to occur.
HO
NaOH
Br
Minor product
Major product
Minor product
In this case, there are two possible
Transcribed Image Text:10.29 We begin by analyzing the reagent. Ethoxide is both a strong nucleophile and a strong base. Next, we look at the substrate, which e secondary. When a secondary substrate is treated with a reagent that is both a strong nucleophile and a strong base, we expect E2 and S 2 products, with the E2 pathway providing the major product. The major product is the trans disubstituted alkene (the Zaitsev product). Minor products include the SN2 product, the cis-disubstituted alkene, and the Hofmann product, as shown here: Br OEt NaOEt Major product Minor product Minor product Minor product 10.30 We begin by analyzing the reagent. Hydroxide is both a strong nucleophile and a strong base. Next, we look at the substrate, which is secondary. When a secondary substrate is treated with a reagent that is both a strong nucleophile and a strong base, we expect E2 and S2 products, with E2 giving the major product. The major product is the trisubstituted alkene (the Zaitsev product). Minor products include the Hofmann elimination product and the S 2 product, as shown below. Notice the configuration of the double bond in the major product. This configuration is dictated by the requirement that the beta proton and the leaving group be antiperiplanar in order for an E2 reaction to occur. HO NaOH Br Minor product Major product Minor product In this case, there are two possible
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