O Macmillan Learning Consider the synthesis of N,N-dimethyl-2-methylhexanamide from diethyl malonate. Fill in the best reagents to achieve this synthetic transformation. NaOH, H₂O NaOEt, EtOH Answer Bank SOCI₂ Na₂ CrO 1 equiv. of (CH3)₂NH BrCH₂CH₂CH₂CH₂ H₂O*, heat 2 equiv. of (CH3)₂NH CH₂ Br 2-bromohexane NaBH4, MeOH 1. 2. 3. 4. 5. 6. 7. 8.
Reactions of Alkyl and Aryl halides
In organic chemistry, an alkyl halide is formed when an atom of hydrogen is switched by a halogen in a hydrocarbon or aliphatic compound. An aryl halide is formed when an atom of hydrogen is substituted by a halogen atom in an aromatic compound. Metals react with aryl halides and alkyl halides and they also go through nucleophilic substitution reactions and elimination reactions.
Zaitsev's Rule in Organic Chemistry
Alexander Zaitsev (also pronounced as Saytzeff), in 1875, prepared a rule to help predict the result of elimination reactions which stated, "The favored product in dehydrohalogenation reactions is that alkene that has the majority of alkyl groups attached to the double-bonded carbon atoms."
Tosylate
Tosylates are important functional groups in organic chemistry, mainly because of two important properties which they possess:
Alkyl Halides
A functional group is a collection of several atoms or bonds with certain characteristic chemical properties and reactions associated with it. There is a presence of a halogen atom (F, Cl, Br, or I; it represents any halogen atom), as a functional group in alkyl halides. Therefore, it can be said that alkanes that contain a halogen compound are called alkyl halides.
![### Synthesis of N,N-dimethyl-2-methylhexanamide from Diethyl Malonate
This exercise involves the synthesis of N,N-dimethyl-2-methylhexanamide starting from diethyl malonate. The task is to fill in the best reagents from the answer bank to achieve this synthetic transformation. Below is the detailed explanation of each step:
1. **Starting Material**:
- *Structure*: Diethyl malonate, characterized by an ester linkage on both ends and a central methylene group flanked by two carbonyl groups.
2. **Product**:
- *Structure*: N,N-dimethyl-2-methylhexanamide, which features an amide linkage central to its structure with N,N-dimethyl groups on the nitrogen atom and a branched hexane chain.
3. **Answer Bank**:
- NaOH, H₂O
- Na₂CrO₇
- H₃O⁺, heat
- NaOEt, EtOH
- 2 equiv. of (CH₃)₂NH
- 1 equiv. of (CH₃)₂NH
- CH₃Br
- SOCl₂
- 2-bromohexane
- BrCH₂CH₂CH₂CH₃
- NaBH₄, MeOH
4. **Procedure**:
- **Step 1**: [Blank]
- **Step 2**: [Blank]
- **Step 3**: [Blank]
- **Step 4**: [Blank]
- **Step 5**: [Blank]
- **Step 6**: [Blank]
- **Step 7**: [Blank]
- **Step 8**: [Blank]
Each of these blanks should be filled with the appropriate reagent from the answer bank to guide the transformation of the diethyl malonate to the target amide. This involves a combination of hydrolysis, alkylation, reduction, and amidation reactions.
### Diagram Explanation
**Structure Diagram**:
- The initial structure features a central carbon atom bound to two ester functional groups.
- The final product illustrates a straight-chain hydrocarbon with a branching methyl group and an amide functional group.
**Mechanistic Steps**:
- The transformation requires](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F67028db1-3c15-42d7-aa43-8659f6c3f0f2%2F293bb760-b88f-491a-bdf0-c6ac10b19dc0%2Fe3u82hm_processed.png&w=3840&q=75)
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