(a)
Interpretation: A mechanism has to be proposed for the given acid-catalyzed formation of the ethoxyethyl protecting group.
Concept introduction:
Hydrolysis is a chemical process in which a molecule is cleaved into two parts by the addition of a molecule of water. If the reaction is carried out with the help of an acid it is said to be an acid catalyzed hydrolysis.
Mechanism of the reaction is the step-by-step description of the process by which reactants are changed into products.
Curved arrows show the bonds that are formed and the bonds that are broken in a reaction.
Curved arrows used to understand a reaction mechanism.
Electrophile: It is positively charged species which seeks for negative charge and hence accepts pair of electrons from negatively charged species (Nucleophiles) which results in the formation of
Nucleophile: It is negatively charged species which seeks for positive charge and hence donate pair of electrons to positively charged species (electrophiles) which results in the formation of chemical bond.
(b)
Interpretation: An experimental procedure has to be suggested whereby the protecting group in the reaction can be removed to regenerate the unprotected alcohol.
Concept introduction:
Hydrolysis is a chemical process in which a molecule is cleaved into two parts by the addition of a molecule of water. If the reaction is carried out with the help of an acid it is said to be an acid catalyzed hydrolysis.
Mechanism of the reaction is the step-by-step description of the process by which reactants are changed into products.
Curved arrows show the bonds that are formed and the bonds that are broken in a reaction.
Curved arrows used to understand a reaction mechanism.
Electrophile: It is positively charged species which seeks for negative charge and hence accepts pair of electrons from negatively charged species (Nucleophiles) which results in the formation of chemical bond.
Nucleophile: It is negatively charged species which seeks for positive charge and hence donate pair of electrons to positively charged species (electrophiles) which results in the formation of chemical bond.
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Chapter 16 Solutions
Organic Chemistry
- Aldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second molecule of alcohol gives an acetal and a molecule of water. We study this reaction in Chapter 16. Draw structural formulas for the hemiacetal and acetal formed from these reagents. The stoichiometry of each reaction is given in the problem.arrow_forwardWhat accounts for the geometry (pyramidalization) of the NH2 group in aniline? 1. Resonance between the NH2 group and the benzene ring. 2. The electronic withdrawing nature of the sp2 carbons in the phenyl group. 3. Participation of the nitrogen lone pair to make the system aromatic. 4. Both 1 and 3.arrow_forwardIn the reaction between 3-pentanone and 1-propanol in the presence of acid catalyst, the resulting FINAL acetal product has bonded to the four different sides of the central carbon. (NOTE: The numbers in the responses should be subscripted.) -СH2CH3, -СН2СНЗ, -ОСН2СH2CH3, and -OН -СН2CH3, -СН2CНЗ, -ОСН2СНЗ, and -OCH2CHЗ -(CH2)4CH3, -(CH2)4CH3, -OCH2CH2CH3, and -OCH2CH2CH3 -CH2CH3, -CH2CH3, -OCH2CH2CH3, and -OCH2CH2CH3 -Н, -СН2СH3, -ОСН2CH2CH3, and -OCH2CH2CHЗarrow_forward
- Write structural formulas for all aldehydes with the molecular formula C6H12O and give each its IUPAC name. Which of these aldehydes are chiralarrow_forwardConsider this compound, which will be referred to as "your compound". a) Name your compound according to the IUPAC system. Include stereochemistry (E/Z/cis/trans/R/S) b) Write the products of your compound and the following reagents. If the reaction would not work for your compound, write "no reaction" and explain the problem. - NaBH4 Croc) Would your compound give a positive Tollen's test? Why or why not د O Consider this compound, which will be referred to as "your compound". H3C. CH3 a) Name your compound according to the IUPAC system. Include stereochemistry (E/Z/cis/trans/R/S) b) Write the products of your compound and the following reagents. If the reaction would not work for your compound, write "no reaction" and explain the problem. NaCN H* HẠNH CH H* NaBH --> CH,MgBr --> CrO3 个 H₁₂O* ------------ c) Would your compound give a positive Tollen's test? Why or why not?arrow_forwardWrite a reaction that could be carried out to synthesize 1-(4-methylphenyl)ethanol (reactants will be a combination of Grignard reagent and carbonyl compound).arrow_forward
- Draw the overall reaction of 2-bromo-2-methylpropane with H2O to give the alcohol product. Include all by-products that form.arrow_forwardDraw structural formulas for the alkenes formed by acid-catalyzed dehydration of each alcohol. Where isomeric alkenes are possible, predict which is the major product. Q.) 1-Methylcyclopentanolarrow_forwardWhich of the following aldehydes has the highest solubility in water? A) CH₃CH₂C(=O)H B) CH₃CH₂CH₂CH₂C(=O)H C) CH₃(CH₂)₅C(=O)H D) CH₃(CH₂)₁₀C(=O)H E) All of these have equal solubility.arrow_forward
- Draw the principal organic product for the reaction of 1-bromopentane with lithium in diethyl ether, followed by formaldehyde in diethyl ether, and then followed by dilute acid.arrow_forwardThe conversion of alcohols into alkyl halides by reaction with hydrogen halides is an example of a Nucleophilic Substitution Reaction. This kind of reaction can proceed by two different mechanisms depending on the structure of alcohol substrates used. Generally, primary alcohols are substituted via SN2 mechanism, while secondary and tertiary alcohols undergo SN1 mechanism. Consider the following reaction given in the picture below and the questions in the picture too.arrow_forward4. A certain endothermic reaction X carried out room temperature (273K) has an enthalpy change of 20 Kcal/mol and an entropy change of 10 Kcal/K/mol. i) Calculate the Gibbs free energy (AG) of this reaction. ii) Is this reaction spontaneous or non-spontaneous? Give a reason for your answer 5. Thiomethane reacts with compound A via an SN1 reaction. Complete its reaction equation below. ii) SH Compound A ii) Draw the mechanism of reaction for this reaction. 6. Butyl Chloride undergoes an elimination reaction when reacted with sodium ethoxide to form butene. The reaction equation is given below with two reaction products A and B. low inevloa CI noitsups p *OEt B Which is the major product, and which is minor product. (Hint: Look up how the size of the base affects the elimination reaction product) Give a reason for your answer.arrow_forward
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