Podcast
Questions and Answers
What is the primary product when an acid chloride undergoes Rosenmund reduction?
What is the primary product when an acid chloride undergoes Rosenmund reduction?
- Carboxylic acid
- Ketone
- Aldehyde (correct)
- Primary alcohol
Which of the following reagents is used in Rosenmund reduction to control the reactivity and prevent over-reduction?
Which of the following reagents is used in Rosenmund reduction to control the reactivity and prevent over-reduction?
- Dialkyl cadmium (R'2Cd)
- Palladium on barium sulfate (Pd-BaSO4) poisoned with quinoline (correct)
- Nickel (Ni)
- Lithium aluminum hydride (LiAlH4)
Which of the following is a limitation of using LiAlH4 or H2/Ni in reducing acid chlorides?
Which of the following is a limitation of using LiAlH4 or H2/Ni in reducing acid chlorides?
- They do not react with acid chlorides.
- They reduce acid chlorides to ketones.
- They require very high temperatures.
- They reduce acid chlorides all the way to primary alcohols. (correct)
What type of compound is produced when an acid chloride reacts with a dialkyl cadmium reagent?
What type of compound is produced when an acid chloride reacts with a dialkyl cadmium reagent?
In the reaction of acid chloride with dialkyl cadmium, what other product is formed besides the ketone?
In the reaction of acid chloride with dialkyl cadmium, what other product is formed besides the ketone?
What is the role of dry ether in the reaction between acid chlorides and dialkyl cadmium?
What is the role of dry ether in the reaction between acid chlorides and dialkyl cadmium?
Starting with ethanoyl chloride (CH3COCl), what is the product of a Rosenmund reduction?
Starting with ethanoyl chloride (CH3COCl), what is the product of a Rosenmund reduction?
Which of the following reactions requires a poisoned catalyst to prevent over-reduction?
Which of the following reactions requires a poisoned catalyst to prevent over-reduction?
In the reaction of acid chloride with dialkyl cadmium to produce a ketone, what byproduct is generated?
In the reaction of acid chloride with dialkyl cadmium to produce a ketone, what byproduct is generated?
If you wanted to convert acetyl chloride to acetone, which of the following reagents would you use?
If you wanted to convert acetyl chloride to acetone, which of the following reagents would you use?
Flashcards
Rosenmund Reduction
Rosenmund Reduction
Acid chloride heated with H2, Pd-BaSO4, and quinoline to obtain aldehyde.
Over-reduction
Over-reduction
LiAlH4 and H2/Ni reduce aldehyde further into primary alcohol.
Acid Chloride + Dialkyl Cadmium
Acid Chloride + Dialkyl Cadmium
Acid chlorides treated w/ dialkyl cadmium in ether yields a ketone
Study Notes
- Alkene structure is indicated by CH3-CH2-CH=CH.
- The double bond in CH3-CH2-CH=CH is located between C3 and C4.
Preparation from Acid Chloride
-
Aldehyde is obtained when acid chloride is heated with H₂ in the presence of Pd-BaSO₄ poisoned by quinoline.
-
This reaction is called Rosenmund reduction.
-
The chemical reaction for Rosenmund reduction is R-CO-Cl + H₂ yielding R-CHO + HCl.
-
Ethanal is produced from Ethanoyl chloride (Acetyl chloride) using Pb-BaSO₄/Quinoline.
-
LiAlH₄ and H₂/Ni can't be used for this reduction.
-
They reduce aldehyde further to primary (1°) alcohol.
-
When acid chlorides are treated with dialkyl cadmium in the presence of ether, ketone is obtained.
-
The chemical reaction for this process is 2 R-CO-Cl + R'₂Cd yielding 2 R-CO-R' + CdCl₂.
-
Acetone is made from acid chloride and dimethyl cadmium in dry ether.
Studying That Suits You
Use AI to generate personalized quizzes and flashcards to suit your learning preferences.
