Organic Chemistry - Alcohol Synthesis Problem

In summary, the conversation revolves around synthesizing an alcohol from an alkyne group. The suggestions include using a hydration reaction, substituting a hydroxyl group with a halide using a selective halide salt, and converting the alkyne to an alkene using Na/liq.NH3. It is also mentioned that the alkyne was incorrectly drawn and should be in a straight line due to sp hybridization. The final step involves mixing an alkene with water to get the desired alcohol.
  • #1
tsaitea
19
0
I have attached a file of the alcohol I need to synthesize and my futile attempt... I was thinking of using a hydration reaction to make the alcohol from the alkyne group. So basically I would mix the alkyne group with H2O and some how produce the alcohol group.

Am I heading in the right direction?
 

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  • #2
It's been a while since I've done Ochem, but here's my suggestion. Hydrate the alkyne, substitute a hydroxyl group with a halide using an equimolar amount of a selective halide salt, like PBr3. The resulting aklene will be on the 1,2 position, and a antimarkovnikov addition of an alcohol should add an alcohol onto the 1 position, creating your desired substance.

By the way, you drew the alkyne incorrectly. It's always drawn in a straight line due to sp hybridization.

EDIT: Actually, what I said was wrong. I was thinking about it on the way to class, removal of the halide will result in the 2,3 alkene, the hydrogen on carbon 2 (the one with the hydroxyl group) will be removed. I'll think about this more.
 
Last edited:
  • #3
Hi!

STEP 1: convert the alkyne to an alkene using Na/liq.NH3 .
STEP 2: Use NBS(N-Bromosuccinimide) to get allyl bromide(CH3CH=CHCH2Br) which when reacted with aq.NaOH gives alcohol(CH3CH=CHCH2OH).
STEP 3: Acidic hydrolysis of this alcohol gives the required product.

Vineeth.
 
  • #4
You're looking to form 1, 3 - butanediol I believe. I'm pretty sure you can mix an alkene with water to get an alcohol.

My organic chem is a bit rusty, but I believe (1 - hydroxy - 2 - butene) + H - OH should give you what you're looking for.
 
  • #5


Yes, you are on the right track by considering a hydration reaction for the synthesis of the alcohol from the alkyne group. However, there are a few considerations that need to be taken into account for a successful synthesis. Firstly, the type of alkyne group and its substituents will affect the reactivity and selectivity of the reaction. Secondly, the choice of reagents and reaction conditions will also play a crucial role in achieving the desired product. It is important to carefully select the appropriate catalyst and solvent for the reaction. Additionally, controlling the reaction temperature and pH can also impact the outcome of the reaction. I would recommend consulting a comprehensive organic chemistry textbook or consulting with a mentor or colleague for guidance on the specific reaction conditions for your desired alcohol synthesis.
 

1. What is Organic Chemistry?

Organic Chemistry is the branch of chemistry that deals with the study of carbon-containing compounds, also known as organic compounds. It focuses on the structure, properties, and reactions of these compounds, which are essential for understanding the behavior of living organisms and materials found in nature.

2. What is Alcohol Synthesis?

Alcohol Synthesis is the process of creating alcohol (specifically ethanol) from other organic compounds. This can be achieved through various methods, including fermentation of sugars by yeast, hydration of alkenes, and reduction of aldehydes or ketones.

3. What is an Alcohol Synthesis Problem?

An Alcohol Synthesis Problem is a question or scenario that requires you to use your knowledge of organic chemistry to synthesize alcohol from a given starting material. This can involve multiple steps and various reactions, and it is a common type of problem encountered in organic chemistry courses.

4. What are some common reactions used in Alcohol Synthesis?

Some common reactions used in Alcohol Synthesis include fermentation, hydration of alkenes, reduction of aldehydes or ketones using reducing agents such as sodium borohydride or lithium aluminum hydride, and Grignard reactions. These reactions allow for the formation of carbon-carbon and carbon-oxygen bonds, which are essential for creating alcohols.

5. How can I improve my skills in solving Alcohol Synthesis Problems?

To improve your skills in solving Alcohol Synthesis Problems, it is essential to have a strong understanding of organic chemistry concepts and reactions. You can also practice by attempting different types of problems, using different starting materials and reaction conditions. Additionally, seeking help from a tutor or professor and studying with peers can also be beneficial in improving your problem-solving abilities.

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