Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 7, Problem 49P
What stereoisomers are obtained when 2-butyne undergoes each of the following reaction sequences?
- a. 1. H2/Lindlar catalyst 2. Br2/CH2Cl2
- b. 1. Na/NH3(1iq), –78°C 2. Br2/CH2Cl2
- c. 1. Cl2/CH2Cl2 2. Br2/CH2Cl2
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
2. Predict the major organic product(s) for each of the following reactions. Be sure to clearly indicate
the proper stereochemical relationships between groups (if appropriate), and write the word
"racemic" next to any compound that is formed as a racemic mixture.
a.
b.
Ph
CH3
CH3
C.
☑
OH
d.
NaOH
H₂O
+
Мон
H2SO4
OH
CH2N2
Et2O
CH3
DCC
H3C
OH
Ph
NH2
1. Predict the major organic product(s) for each of the following reactions. Be sure to clearly indicate
the proper stereochemical relationships between groups (if appropriate), and write the word
"racemic" next to any compound that is formed as a racemic mixture.
a.
b.
C.
d.
H
H3C
CH3
aq. KOH, A
H₂N
CH3
OH
CH3
HO
Ph
H
CH3OH
PhH, A
+
Ph 'N'
H
CH3
HS
SH
BF3
teYr + {,,trs,£
CH3
H3C
H
e.
HO
N
H2SO4
Ph.
CH3
f.
CH3
p-TSOH
H3C
H
2 eq. CH3OH
g.
h.
H3C
Ph
H3O+
Ph
H
HO-NH2
AcOH
Which of the following reactions or series of reactions will lead to the formation of
methoxycyclohexane?
OH
CH₂OH/A
1. CH3MgBr/ ether
2. H*/H₂O
1. Na
2. CH₂CH₂I
1. Hg(OAc)2/ CH₂OH
2. NaBH4
1. MCPBA
2. H¹/ CH₂OH
Chapter 7 Solutions
Organic Chemistry (8th Edition)
Ch. 7.1 - Prob. 1PCh. 7.1 - Name the following:Ch. 7.1 - What is the molecular formula for a monocyclic...Ch. 7.1 - Draw the condensed and skeletal structures for...Ch. 7.1 - Draw the structure and give the common and...Ch. 7.2 - Prob. 6PCh. 7.2 - Name the following:Ch. 7.3 - What orbitals are used to form the carbon-carbon ...Ch. 7.4 - Prob. 9PCh. 7.4 - Why does cis-2-butene have a higher boiling point...
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 - Prob. 23PCh. 7.10 - Rank the following from strongest base to weakest...Ch. 7.10 - Prob. 26PCh. 7.12 - Prob. 28PCh. 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. 32PCh. 7 - What is each compounds systematic name?Ch. 7 - What reagents should be used to carry out the...Ch. 7 - Prob. 35PCh. 7 - Draw the mechanism for the following reaction:Ch. 7 - Prob. 37PCh. 7 - Prob. 38PCh. 7 - What is the major product of the reaction of 1 mol...Ch. 7 - Answer Problem 39, parts a-b, using 2-butyne as...Ch. 7 - What is each compounds systematic name? a....Ch. 7 - What is the molecular formula of a hydrocarbon...Ch. 7 - a. Starting with 3-methyl 1-butyne, how can you...Ch. 7 - Prob. 44PCh. 7 - Which of the following pairs are keto-enol...Ch. 7 - Prob. 46PCh. 7 - Do the equilibria of the following acid-base...Ch. 7 - What is each compounds systematic name?Ch. 7 - What stereoisomers are obtained when 2-butyne...Ch. 7 - Prob. 50PCh. 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. 54PCh. 7 - What stereoisomers are obtained from the following...Ch. 7 - Prob. 56PCh. 7 - Prob. 57PCh. 7 - Prob. 58PCh. 7 - Show how the following compound can be prepared...Ch. 7 - Prob. 60P
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 1. Predict the major organic product(s) for each of the following reactions. Be sure to clearly indicate the proper stereochemical relationships between groups (if appropriate), and write the word "racemic" next to any compound that is formed as a racemic mixture. a. b. C. d. e. f. g. h. H₂N- Ph HS HO. Ph. H3C H3C CH3 CH3 Ph CH3 H3C CH3 CH3 CH3 SH + H me Ph CH3OH + Ph H3C H₂SO4 p-TsOH 2 eq. CH3OH H30Ⓡ HO-NH2 ACOH aq. KOH, A OH HO H CH3 BF3 PhH, Aarrow_forwardWhich stereoisomer would be produced from the reaction of trans-2-butene with OsO4 followed by H2O2? A. 2S,3S- diol and 2R, 3R-diol B. 2S,3R-diol and 2R,3S-diol C. 2S,3S-diol only D. 2R, 3R-diol only E. 2S,3R-diol onlyarrow_forwardName each alkene and specify its configuration by the E,Z system. Cl- Cl I a. b. Br С.arrow_forward
- Ff.154.arrow_forwardCan you explain the reasons and concepts for why these answers are true?arrow_forward1. Cl₂, FeCl3 2. Mg, ether 3. 4. Mild H₂O+ 5. SOCI₂ 6. NaCN 7. H₂O¹, heat 8. SOCI 9. AlCl3 Work out the synthesis on a separate sheet of paper, and then draw the structure of the final organic product(s). • You do not have to consider stereochemistry. • If an ortho/para mixture is formed, draw both isomers. • Do not draw organic or inorganic by-products. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate multiple products using the + sign from the drop-down menu.arrow_forward
- Q-I: For this energy diagram, associated with rotating the carbon-carbon bond structure, draw Newman projections for each letter within the diagram. А. B CI CI н-с-с-н ČI ĆI В. E С. D. C-C dihedral angle Q-II: Determine and draw out the product(s), as well as the reaction mechanism(s), for this nucleophilic substitution rxn. Br ONa O2N' Q-III: Determine and draw out the product(s) and reaction mechanism(s) for each step in this rxn. NaO, NaN3 HC1 но 'Brarrow_forwardDraw the structure of the major organic product of the following reaction. H CH3CH2 CH₂CH3 CH₂CH3 1. Hg(OAC)₂, H₂O 2. NaBH4 . You do not have to consider stereochemistry. • In cases where there is more than one answer, just draw one.arrow_forward7. Fill in the missing information.arrow_forward
- What is the major product obtained from treating an excess of each of the following compounds with Cl2 in the presence of ultraviolet light at room temperature? Disregard stereoisomers.arrow_forward8. A) B) Provide the reagents necessary to carry out the following conversion. 1. H₂O/ H₂SO4, 2. PCC/CH₂Cl2 PCC/ CH₂Cl2 1. BH3, 2. H₂O2/NaOH/H₂O 1. 03, 2. Zn/acetic acid 1. BH3, 2. H₂O2/NaOH/H₂O, 3. PCC Harrow_forwardWhich reagents lead to this transformation? - O1. CH3CH2CI, AICI3 2. Cl2, AICI3 O 1. Cl2, AICI3 2. CH3CH2CI, AICI3 O1. Cl2, AICI3 2. CH3COCI, AICI3 3. Zn(Hg), HCI O1. CH3COCI, AICI3 2. Cl2, AICI3 3. Zn(Hg), HCIarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY