Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 7, Problem 40P
Answer Problem 39, parts a-b, using 2-butyne as the starting material instead or propyne.
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PQ-2. This reaction is classified as
(A) a nucleophilic addition.
(C) a nucleophilic substitution.
NaCN
H3C CH3
H₂O
(B) an electrophilic addition.
(D) an electrophilic substitution.
HO
H3C
CN
CH3
Draw structures for compounds A through D.
1. NaOH, H2O
A
2. H,0°A
1. NaOEt, EtOH
(a) Ethyl acetoacetate
→ B
2. 1-Chloro-4-methylpentane
Same as above
1. NaOH, H2O
D
1. NaOC(CH3)3, (CH3);COH
(b) A
2. 1-Chloropropane
2. H,0ºA
CH3 CH3
CH3
CH;=ĊCH,CHCH;OH
H2SO4, H3C
H3C
Referring to the above reaction:
1. Which atom does the H2SO4 first remove?
2. Identify the reaction if it's hydrogenation, hydrohalogenation, etc.
3. Propose a mechanism for the reaction, using the arrow formalism to indicate the flow of electrons.
Chapter 7 Solutions
Organic Chemistry
Ch. 7.1 - What is the molecular formula for a monocyclic...Ch. 7.1 - Prob. 2PCh. 7.1 - Draw the structure and give the common and...Ch. 7.1 - Prob. 4PCh. 7.1 - Name the following:Ch. 7.2 - Prob. 6PCh. 7.2 - Name the following:Ch. 7.3 - Prob. 8PCh. 7.3 - Why does cis-2-butene have a higher boiling point...Ch. 7.4 - What orbitals are used to form the carbon-carbon ...
Ch. 7.6 - Prob. 12PCh. 7.6 - Prob. 13PCh. 7.7 - Prob. 14PCh. 7.7 - Which alkyne should be used for the synthesis of...Ch. 7.7 - Prob. 16PCh. 7.8 - Prob. 17PCh. 7.8 - Only one alkyne forms an aldehyde when it...Ch. 7.9 - Describe the alkyne you should start with and the...Ch. 7.9 - Prob. 20PCh. 7.10 - Prob. 21PCh. 7.10 - Prob. 22PCh. 7.10 - Rank the following from strongest base to weakest...Ch. 7.12 - Prob. 26PCh. 7 - What is the major product obtained from the...Ch. 7 - Draw a condensed structure for each of the...Ch. 7 - A student was given the structural formula of...Ch. 7 - Prob. 30PCh. 7 - What is each compounds systematic name?Ch. 7 - What reagents should be used to carry out the...Ch. 7 - Prob. 33PCh. 7 - Prob. 34PCh. 7 - Prob. 35PCh. 7 - Prob. 36PCh. 7 - What is the major product of the reaction of 1 mol...Ch. 7 - What is each compounds systematic name? a....Ch. 7 - What is the molecular formula of a hydrocarbon...Ch. 7 - Answer Problem 39, parts a-b, using 2-butyne as...Ch. 7 - Prob. 41PCh. 7 - a. Starting with 3-methyl 1-butyne, how can you...Ch. 7 - Prob. 43PCh. 7 - Which of the following pairs are keto-enol...Ch. 7 - Prob. 45PCh. 7 - Do the equilibria of the following acid-base...Ch. 7 - What stereoisomers are obtained when 2-butyne...Ch. 7 - Draw the keto tautomer for each of the following:Ch. 7 - Show how each of the following compounds can be...Ch. 7 - A chemist is planning to synthesize 3-octyne by...Ch. 7 - Prob. 51PCh. 7 - What stereoisomers are obtained from the following...Ch. 7 - Prob. 53PCh. 7 - Prob. 54PCh. 7 - Prob. 55PCh. 7 - Prob. 56PCh. 7 - Prob. 57P
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- CCH H20, H2SO4 H9SO4 CH3 Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Hjö: -CH3 -CH3 H3O*arrow_forwardI. Using Markovnikov's rule, predict the predominant product in each of the following addition reaction а. CНз—СH—CH-—СH—СH, + HBr —> b. + HCl → с. СН;—СН—CH—СH,—СН, + HBr —> CH—CH—СН,—СH; + HCI -> D. + HBr → E.arrow_forwardReagent 5 options; H2O H+CrO3 H2SO4 H2O CH3CH2Br NaBH4arrow_forward
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