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Consider the following reactions (1) ...

Consider the following reactions
(1) `(CH_3)_3"CC"H(OH)CH_3overset("conc".H_2SO_4)rarr`
(2) `(CH_3)_2"CHCH(Br)CH_(3)overset(conc.KOH)rarr`
(3) `(CH_3)_2"CHCH(Br)CH_(3)overset((CH_3)_3CO^(-) Koplus)rarr`
(4) `(CH_3)_2underset( "OH ")underset(" | ")(C-CH_2)-CHOoverset(Delta)rarr`
Which of these reaction(s) will produce Saytzeff product?

A

(1) , (2) and (4)

B

(3) only

C

(4) only

D

(2) and (4)

Text Solution

AI Generated Solution

The correct Answer is:
To determine which of the given reactions produce the Saytzeff product, we will analyze each reaction step by step. ### Reaction 1: **Reaction:** \((CH_3)_3C(OH)CH_3 \overset{\text{conc. } H_2SO_4}{\rightarrow}\) 1. **Protonation of Alcohol:** The hydroxyl group (OH) is protonated by concentrated sulfuric acid, forming a better leaving group (water). 2. **Formation of Carbocation:** The water molecule leaves, leading to the formation of a tertiary carbocation \((CH_3)_3C^+\). 3. **Carbocation Rearrangement:** Since we have a tertiary carbocation, it is stable and does not rearrange further. 4. **Deprotonation:** A proton is removed from a neighboring carbon, resulting in the formation of a double bond. The double bond forms between the carbon with the carbocation and the adjacent carbon. 5. **Product:** The product is a double bond between the carbons, leading to a more substituted alkene (Saytzeff product). ### Reaction 2: **Reaction:** \((CH_3)_2CHCH(Br)CH_3 \overset{\text{conc. KOH}}{\rightarrow}\) 1. **Base Abstraction:** The concentrated KOH acts as a strong base and abstracts a proton from the carbon adjacent to the carbon bonded to bromine (Br). 2. **Elimination Reaction:** The Br leaves as a leaving group, resulting in the formation of a double bond. 3. **Product:** The product is a double bond between the carbons, leading to a more substituted alkene (Saytzeff product). ### Reaction 3: **Reaction:** \((CH_3)_2CHCH(Br)CH_3 \overset{(CH_3)_3CO^-}{\rightarrow}\) 1. **Bulky Base Action:** The bulky base \((CH_3)_3CO^-\) will abstract a proton from the less substituted carbon due to steric hindrance. 2. **Elimination Reaction:** The Br leaves, and a double bond is formed. 3. **Product:** This results in a less substituted alkene (Hofmann product), not a Saytzeff product. ### Reaction 4: **Reaction:** \((CH_3)_2CHO \overset{(C-CH_2)-CHO \Delta}{\rightarrow}\) 1. **Heating with Aldehyde:** The reaction involves heating with an aldehyde, which can lead to dehydration. 2. **Formation of Double Bond:** The reaction can lead to the formation of a double bond. 3. **Product:** Depending on the structure, this can lead to a more substituted alkene (Saytzeff product). ### Conclusion: From the analysis: - **Reactions 1, 2, and 4** produce Saytzeff products. - **Reaction 3** produces a Hofmann product. ### Final Answer: The reactions that produce Saytzeff products are **1, 2, and 4**.
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