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17-30 Answer true or false.
(a) The reduction of an
(b) The reduction of a
(c) The oxidation of an aldehyde gives a
(d) The oxidation of a primary alcohol gives a ketone.
(e) Tollens’ reagent can be used to distinguish between an aldehyde and a ketone.
(f) Sodium borohydride, NaBH4, reduces an aldehyde to a primary alcohol.
(g) The addition of one molecule of alcohol to the carbonyl group of a ketone gives a hemiacetal.
(h) The reaction of an aldehyde with two molecules of alcohol gives an acetal, plus a molecule
of water.
(j) The formation of hemiacetals and acetals is reversible.
(j) The cyclic hemiacetal formed from 4-hydroxy-pentanal has two stereocenters and can exist as
a mixture of 22 = 4 stereoisomers.
(a)
Interpretation:
Answer true or false for the following statement.
The reduction of an aldehyde always gives an alcohol.
Concept Introduction:
Reduction is the addition of a hydrogen atom to a compound.
Answer to Problem 22P
The given statement is true.
Explanation of Solution
In aldehydes, the functional group is
Oxidation of aldehydes forms primary alcohol. For example, reduction of pentanal gives 1-pentanol.
Therefore, the given statement is true.
(b)
Interpretation:
Answer true or false for the following statement.
The reduction of ketones always gives a secondary alcohol.
Concept Introduction:
Aldehydes and ketones contain carbonyl group as a functional group. Reduction is the addition of a hydrogen atom to a compound.
Answer to Problem 22P
Therefore, the given statement is true.
Explanation of Solution
Reduction of ketones, hydrogen is added to the carbonyl carbon and gives secondary alcohol.
Therefore, the given statement is true.
(c)
Interpretation:
Answer true or false for the following statement.
The oxidation of aldehydes gives a carboxylic acid.
Concept Introduction:
Aldehydes and ketones contain carbonyl group as a functional group. Oxidation is the process in which oxygen is added to the molecule.
Answer to Problem 22P
The given statement is true.
Explanation of Solution
Oxidation of aldehydes, oxygen is added to the carbonyl group and form carboxylic acid.
Therefore, the given statement is true.
(d)
Interpretation:
Answer true or false for the following statement.
The oxidation of primary alcohol gives ketone.
Concept Introduction:
Aldehydes and ketones contain carbonyl group as a functional group. Oxidation is the process in which oxygen is added to the molecule.
Answer to Problem 22P
The given statement is false.
Explanation of Solution
Oxidation of primary alcohol first converted into aldehyde and followed by carboxylic acids.
Therefore, the given statement is false.
(e)
Interpretation:
Answer true or false for the following statement.
Tollen’s reagent can be used to distinguish between an aldehyde and a ketone.
Concept Introduction:
Tollen’s reagent is a mild oxidizing agent.
Tollen’s reagent is reacts with the aldehyde group of a compound. The carbonyl group acts as a reducing agent and reduces the silver ion of the Tollen’s regent to silver metal.
Answer to Problem 22P
The given statement is true.
Explanation of Solution
Aldehydes undergo oxidation easily, even with mild oxidizing agents and give carboxylic acid.
Ketone does not undergo oxidation with mild oxidizing agent due to selectivity of aldehyde and ketone for oxidation is used to differentiate an aldehyde and a ketone. Therefore, aldehyde and ketones are distinguished by using Tollen’s regent.
Therefore, the given statement is true.
(f)
Interpretation:
Answer true or false for the following statement.
Sodium borohydride,
Concept Introduction:
Aldehydes and ketones contain carbonyl group as a functional group. The aldehydes undergoes a reduction reaction where in the addition of hydrogen occurs at the double bond between the oxygen and the carbon of the carbonyl group present in the aldehyde.
Answer to Problem 22P
Therefore, the given statement is true.
Explanation of Solution
(g)
Interpretation:
Answer true or false for the following statement.
The addition of one molecule of alcohol to the carbonyl group of a ketone gives a hemiacetal.
Concept Introduction:
Aldehydes and ketones contain carbonyl group as a functional group. In Hemiacetal, carbon is added to hydroxyl group and alkoxy group.
Answer to Problem 22P
The given statement is true.
Explanation of Solution
When a molecule of alcohol is added to a ketone, the hydrogen of the alcohol is added o the oxygen atom of the carbonyl group, while the alkoxy group of the alcohol is added to the carbon of the carbonyl group. Hence ketone forms hemiacetal when the reacts with one molecule of alcohol.
Therefore, the given statement is true.
(h)
Interpretation:
Answer true or false for the following statement.
The reaction of an aldehyde with two molecules of alcohol gives an acetal, plus a molecule of water.
Concept Introduction:
Aldehydes and ketones contain carbonyl group as a functional group. In acetal, carbon is bonded to two alkoxy groups.
Answer to Problem 22P
The given statement is true.
Explanation of Solution
Two molecules of an alcohol are added to an aldehyde to form hemiacetal. And it is unstable and it reacts with another molecule of an alcohol in the presence of an acid forms acetal and water.
Therefore, the given statement is true.
(i)
Interpretation:
Answer true or false for the following statement.
The formation of hemiacetals and acetal is reversible.
Concept Introduction:
Aldehydes and ketones contain carbonyl group as a functional group. In Hemiacetal, carbon is added to hydroxyl group and alkoxy group. In acetal, carbon is added to a two alkoxy groups.
Answer to Problem 22P
The given statement is true.
Explanation of Solution
By using large excess of alcohol hemiacetals and acetals are reversible by the removal of water molecules. To shift the equilibrium towards the left side by the hydrolysis of the acetal to the aldehyde or ketone and alcohol.
Therefore, the given statement is true.
(j)
Interpretation:
Answer true or false for the following statement.
The cyclic hemiacetal formed from 4-hydroxypentanal has two stereocentres and can exists as a mixture of
Concept Introduction:
A stereocentre is a carbon atom with four different groups bonded to it. The stereocentres of molecule can be calculated by using
n= stereocentre.
Answer to Problem 22P
The given statement is true.
Explanation of Solution
The cyclic hemiacetal; obtained from 4-hydroxypentanal has two stereocenters.
4- hydroxypentanal has two stereocenters, therefore it have 4 stereoisomers.
Therefore, the given statement is true.
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Chapter 16 Solutions
EP INTRO.TO GENERAL,ORGANIC...-OWL ACCE
- 19.78 Write the products of the following sequences of reactions. Refer to your reaction road- maps to see how the combined reactions allow you to "navigate" between the different functional groups. Note that you will need your old Chapters 6-11 and Chapters 15-18 roadmaps along with your new Chapter 19 roadmap for these. (a) 1. BHS 2. H₂O₂ 3. H₂CrO4 4. SOCI₂ (b) 1. Cl₂/hv 2. KOLBU 3. H₂O, catalytic H₂SO4 4. H₂CrO4 Reaction Roadmap An alkene 5. EtOH 6.0.5 Equiv. NaOEt/EtOH 7. Mild H₂O An alkane 1.0 2. (CH3)₂S 3. H₂CrO (d) (c) 4. Excess EtOH, catalytic H₂SO OH 4. Mild H₂O* 5.0.5 Equiv. NaOEt/EtOH An alkene 6. Mild H₂O* A carboxylic acid 7. Mild H₂O* 1. SOC₁₂ 2. EtOH 3.0.5 Equiv. NaOEt/E:OH 5.1.0 Equiv. NaOEt 6. NH₂ (e) 1. 0.5 Equiv. NaOEt/EtOH 2. Mild H₂O* Br (f) i H An aldehyde 1. Catalytic NaOE/EtOH 2. H₂O*, heat 3. (CH,CH₂)₂Culi 4. Mild H₂O* 5.1.0 Equiv. LDA Br An ester 4. NaOH, H₂O 5. Mild H₂O* 6. Heat 7. MgBr 8. Mild H₂O* 7. Mild H₂O+arrow_forwardLi+ is a hard acid. With this in mind, which if the following compounds should be most soluble in water? Group of answer choices LiBr LiI LiF LiClarrow_forwardQ4: Write organic product(s) of the following reactions and show the curved-arrow mechanism of the reactions. Br MeOH OSO2CH3 MeOHarrow_forward
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