Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Question
Chapter 16.4, Problem 13P
(a)
Interpretation Introduction
Interpretation:
The preparation method has to be given for the given compound using ethyne as one of the starting material.
(b)
Interpretation Introduction
Interpretation:
It should be explained that why ethyne should be carried alkylation reaction before, rather than after nucleophilic addition.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
a. Show how the following compounds can be prepared, using ethyne as one of the starting materials:1. 1-pentyn-3-ol 2. 1-phenyl-2-butyn-1-ol 3. 2-methyl-3-hexyn-2-ol
b. Explain why ethyne should be alkylated before, rather than after, nucleophilic addition.
Which best describes this transformation?
Meo,C CO,Me
Et
NaOMe (2 equivalents)
MeOH
Et
H,N NH2
HN
NH
Et
Et
A. Two intermolecular nucleophilic acyl substitutions
B. Two intramolecular nucleophilic acyl substitutions
C. An intramolecular followed by an intermolecular nucleophilic acyl substitutions
D. An intermolecular followed by an intramolecular nucleophilic acyl substitutions
16. Rank the species below in order of increasing nucleophilicity in protic solvents:
CH3CO2-, CH3S-, HO-, H2O.
Answer:
A. H2O
Chapter 16 Solutions
Organic Chemistry (8th Edition)
Ch. 16.1 - Give two names for each of the following:Ch. 16.1 - Prob. 2PCh. 16.1 - Name the following:Ch. 16.2 - Prob. 4PCh. 16.4 - What products are formed when the following...Ch. 16.4 - We saw on the previous page that...Ch. 16.4 - a. How many stereoisomers are obtained from the...Ch. 16.4 - Prob. 9PCh. 16.4 - Write the mechanism for the reaction of acetyl...Ch. 16.4 - Prob. 11P
Ch. 16.4 - Show how the following compounds can be...Ch. 16.4 - Prob. 13PCh. 16.4 - Prob. 14PCh. 16.4 - In the mechanism for cyanohydrin formation, why is...Ch. 16.4 - Prob. 16PCh. 16.4 - Prob. 17PCh. 16.4 - Show two ways to convert an alkyl halide into a...Ch. 16.5 - Prob. 20PCh. 16.5 - Prob. 21PCh. 16.5 - Prob. 22PCh. 16.5 - Prob. 23PCh. 16.6 - Prob. 24PCh. 16.7 - What reducing agents should be used to obtain the...Ch. 16.7 - Prob. 26PCh. 16.8 - Prob. 27PCh. 16.8 - Prob. 28PCh. 16.8 - Prob. 29PCh. 16.8 - The pKa of protonated acetone is about 7.5. and...Ch. 16.8 - Prob. 31PCh. 16.8 - Prob. 32PCh. 16.8 - Prob. 33PCh. 16.8 - Excess ammonia must be used when a primary amine...Ch. 16.8 - The compounds commonly known as amino acids are...Ch. 16.9 - Hydration of an aldehyde is also catalyzed by...Ch. 16.9 - Which ketone forms the most hydrate in an aqueous...Ch. 16.9 - When trichloroacetaldehyde is dissolved in water,...Ch. 16.9 - Which of the following are a. hermiacetals? b....Ch. 16.9 - Prob. 40PCh. 16.9 - Explain why an acetal can be isolated but most...Ch. 16.10 - Prob. 42PCh. 16.10 - Prob. 43PCh. 16.10 - What products would be formed from the proceedings...Ch. 16.10 - a. In a six-step synthesis, what is the yield of...Ch. 16.10 - Show how each of the following compounds could be...Ch. 16.12 - Prob. 47PCh. 16.13 - Prob. 49PCh. 16.14 - Prob. 50PCh. 16.15 - Prob. 51PCh. 16.16 - Prob. 52PCh. 16 - Draw the structure for each of the following: a....Ch. 16 - Prob. 54PCh. 16 - Prob. 55PCh. 16 - Prob. 56PCh. 16 - a. Show the reagents required to form the primary...Ch. 16 - Prob. 58PCh. 16 - Prob. 59PCh. 16 - Using cyclohexanone as the starting material,...Ch. 16 - Propose a mechanism for each of the following...Ch. 16 - Show how each of the following compounds can be...Ch. 16 - Fill in the boxes:Ch. 16 - Prob. 64PCh. 16 - Identify A through O:Ch. 16 - Prob. 66PCh. 16 - Prob. 67PCh. 16 - Prob. 68PCh. 16 - How many signals would the product of the...Ch. 16 - Prob. 70PCh. 16 - Prob. 71PCh. 16 - Prob. 72PCh. 16 - Prob. 73PCh. 16 - Prob. 74PCh. 16 - Prob. 75PCh. 16 - Prob. 76PCh. 16 - Prob. 77PCh. 16 - Prob. 78PCh. 16 - Draw structure for A-D for each of the following:Ch. 16 - Prob. 80PCh. 16 - a. Propose a mechanism for the following reaction:...Ch. 16 - Prob. 82PCh. 16 - A compound gives the following IR spectrum. Upon...Ch. 16 - How can be following compounds be prepared from...Ch. 16 - Prob. 85PCh. 16 - Prob. 86PCh. 16 - Prob. 87PCh. 16 - In the presence of an acid catalyst, acetaldehyde...Ch. 16 - Prob. 89PCh. 16 - Prob. 90PCh. 16 - Prob. 91PCh. 16 - A compound reacts with methylmagnesium bromide...Ch. 16 - Show how each of the following compounds can be...Ch. 16 - Prob. 94PCh. 16 - The pKa values of the carboxylic acid groups of...Ch. 16 - The Baylis-Hillman reaction is a DABCO...Ch. 16 - Prob. 97PCh. 16 - Prob. 98P
Knowledge Booster
Similar questions
- 12. What alkyl halide and nucleophile are needed to prepare the following compounds? a. b. OHarrow_forwardThe following reaction takes place several times faster than the reaction of 2-chlorobutane with HO-: a. Explain the enhanced reaction rate.b. Explain why the OH group in the product is not bonded to the carbon that was bonded to the Cl group in the reactant.arrow_forwardThe reaction will proceed with mechanism because the secondary alkyl halide react with nucleophile. + NaOCH3 Br CH3 O a. SN2, strong O b. SN1, strong O c. SN1, weak O d. SN2, weakarrow_forward
- 2. Show the products of reaction between each organometallic reagent below with the given proton source. a. b. C. d. e. Li MgBr Li MgBr + + + H H-Br OH H HSarrow_forward4. Derive the major product for the following E1 and E2 elimination reactions a. b. NEt3 NEt3 Br NaOEt EtOH t-BuOK t-BuOHarrow_forwardIdentify the best reagents to complete the following reaction. 1. NaOH A 2. CH3CH2CH2NH2 1. HCI В 2. CH3CH2CH2NH2 ОН CH3CH2CH2NH2 C 1. SOCI2 D 2. CH3CH2CH2NH2 1. CH3CH2CH2NH2 E 2. SOCI2 NH,arrow_forward
- A 3. Rank the following compounds in terms of reactivity with a good nucleophile. Br B NH₂ F D OH E CIarrow_forwarda. HO b. NH 33. Which is a better nucleophile? a. H₂O or HO c. H₂S b. NH3 or NH₂ C. CH, CO in a better leaving group. or CH3CH₂O d. -0 or -0arrow_forwardExplain why the reaction is SN1 and not SN2 PS: the OH shouldnt be on the phenyl.arrow_forward
- Fill in the missing reagents a-e in the following scheme:arrow_forwardWhat is the major elimination product expected from the following reaction? Br. NaOMe MeOH Select one: a. b. Od.arrow_forwardSynthesize the following compound from cyclohexanol, ethanol, and any other needed reagents. 2 Part 1 out of 3 Preparation of the Grignard reagent: ok nt nces A OH draw structure ... draw structure ... Draw the intermediate product formed above and select the correct reagent for A. O MgBr, O HBr O NaBr O Br2 Draw the Grignard reagent formed above and select the correct reagent for B. O Mgo O MgBr O MgI, O Mg Hint Solution e to search K.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you