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Chapter 11: Q15. (page 442)

Question: Draw the organic products formed in each reaction

a.

b.

Short Answer

Expert verified

Answer

a.

b.

Step by step solution

01

Step-by-Step Solution Step 1: Reaction of Acetylide anion

Acetylides are compounds having a terminal alkyne group in their structure. When these compounds are treated with a strong base, acetylide anions are formed.

The general reaction is shown below

Formation of acetylide anion

02

Formation of acetylide anion

After the acetylide anions are formed, they act as strong nucleophile and can participate in nucleophilic substitution when reacted with alkyl halides.A general reaction is shown below:

Type reaction of acetylide with an alkyl halide

03

Mechanism for a

a.

The base attacks at the terminal alkyne hydrogen, and the nucleophile is formed. The nucleophile then attacks at the alkyl halide given.

The mechanism is given below:

Acetylide anion reaction with the given alkyl halide

04

Mechanism for the reaction

b.

The mechanism of the reaction is mentioned below:

Acetylide anion reaction with the given alkyl halides

With the 3掳 alkyl halide, elimination takes place rather than substitution since the carbocation is too crowded for substitution to occur.

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Most popular questions from this chapter

Question: Write a stepwise mechanism for each of the following reactions. Explain why a more stable alkyne (but-2-yne) is isomerized to a less stable alkyne (but-1-yne), but under similar conditions, 2,5-dimethylhex-3-yne forms 2,5-dimethylhexa-2,3-diene.

Question: Synthesize each compound from acetylene. You may see any other organic or inorganic reagents.

a.

b.

c.

d.

e.

Question: Use retrosynthetic analysis to show how hex-3-yne can be prepared from acetylene and any other organic and inorganic compounds. Then draw the synthesis in the synthetic direction, showing all needed reagents.

Question: Draw the enol form of each keto tautomer in parts (a) and (b), and the keto form of each enol tautomer in parts (c) and (d).

a.

b.

c.

d.

Question: Show how HC鈮�CH,(CH3)2CHCH2CH2Brcan be used to prepare CH3CH2C鈮�CCH2CH2CH(CH3)2 . Show all reagents, and use curved arrows to show movement of electron pairs.
See all solutions

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