ORG.CHEM.WILEYPLUSNEXTGEN.W/LLTEXT+STDY.
4th Edition
ISBN: 9781119832638
Author: Klein
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 7, Problem 55PP
(a)
Interpretation Introduction
Interpretation:
Suitable nucleophile and alkyl iodide must be identified for the preparation of butan-1-ol.
Concept Introduction :
The SN2 substitution can be used to prepare primary alcohols from primary
(b)
Interpretation Introduction
Interpretation:
Suitable combination of alkyl iodide and nucleophile must be identified for the preparation of butyl ethanoate.
Concept Introduction :
The SN2 reaction can be used for for the preparation of ester using sodium salt of
(c)
Interpretation Introduction
Interpretation:
The suitable combination of iodoalkane and nucleophile must be identified for the given cyano compound.
Concept Introduction :
The SN2 reaction is characterized by inversion of configuration which is caused due to backside attack of the nucleophile.
(d)
Interpretation Introduction
Interpretation:
For the given thiol, proper iodoalkane and nucleophile must be identified.
Concept Introduction:
The SN2 reaction is associated with inversion of configuration. Proper stereochemistry of starting material must be chosen to get the desired stereochemistry of product after inversion of configuration.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
d. 3,4,5-trimethoxybenzoyl chloride
. What is the order of decreasing reactivity towards nucleophilic acyl substitution for the
arboxylic acid derivatives? (most reactive first)
A.
B.
0
0
O
0
0
H3C-C-O-C-CH3 H3C-C-N(CH3)2 H3C-C-OCH 3
(CH3)2CH-C-OCH3
I
||
။
IV
a.
I, II, III, IV
b. I, III, IV, II
C.
II, IV, III, I
d. II, I, III, IV
0
0
0
0
0
R-C-O C-R R-C-NH2
R-C OR
R-C-CI
a.
I, III, II, IV |
11
III
IV
b.
II, III, I, IV
c.
III, II, I, IV
d.
IV, I, III, II
B.
d. a hydrate
4. Give the major organic product(s) for each of the following reactions or sequences of reactions. Show
all relevant stereochemistry [4 ONLY].
A.
CH₂OH
PCC
CH2Cl2
0
H
KCN
HCN
2
Propose a synthesis of the anti-inflammatory drug Ibuprofen from benzene. Show all reagents and all
intermediate structures. Assume that ortho and para isomers can be separated.
(CH3)2CHCH2
CH3
CHCOOH 1buprofen
be required
Chapter 7 Solutions
ORG.CHEM.WILEYPLUSNEXTGEN.W/LLTEXT+STDY.
Ch. 7.2 - Prob. 1CCCh. 7.3 - Prob. 2CCCh. 7.3 - Prob. 1LTSCh. 7.3 - Prob. 3PTSCh. 7.3 - Prob. 4ATSCh. 7.3 - Prob. 2LTSCh. 7.3 - Prob. 5PTSCh. 7.3 - Prob. 6ATSCh. 7.3 - Prob. 7CCCh. 7.4 - Prob. 8CC
Ch. 7.5 - Prob. 9CCCh. 7.6 - Prob. 10CCCh. 7.6 - Prob. 11CCCh. 7.7 - Prob. 12PTSCh. 7.7 - Prob. 13PTSCh. 7.7 - Prob. 14ATSCh. 7.7 - Prob. 4LTSCh. 7.7 - Prob. 16ATSCh. 7.7 - Prob. 17CCCh. 7.7 - Prob. 18CCCh. 7.7 - Prob. 5LTSCh. 7.7 - Prob. 19PTSCh. 7.7 - Prob. 20ATSCh. 7.8 - Prob. 21PTSCh. 7.8 - Prob. 22ATSCh. 7.8 - Prob. 23CCCh. 7.8 - Prob. 24CCCh. 7.8 - Prob. 25CCCh. 7.8 - Prob. 26CCCh. 7.8 - Prob. 27CCCh. 7.9 - Prob. 7LTSCh. 7.9 - Prob. 29ATSCh. 7.9 - Prob. 30ATSCh. 7.9 - Prob. 31ATSCh. 7.10 - Prob. 32CCCh. 7.10 - Prob. 33CCCh. 7.10 - Prob. 34CCCh. 7.11 - Prob. 8LTSCh. 7.11 - Prob. 35PTSCh. 7.11 - Prob. 36PTSCh. 7.11 - Prob. 37ATSCh. 7.11 - Prob. 9LTSCh. 7.11 - Prob. 40PTSCh. 7.11 - Prob. 41ATSCh. 7.12 - Prob. 42CCCh. 7.12 - Prob. 43CCCh. 7.12 - Prob. 44CCCh. 7.12 - Prob. 45CCCh. 7.12 - Prob. 46CCCh. 7 - Prob. 47PPCh. 7 - Prob. 48PPCh. 7 - Prob. 49PPCh. 7 - Prob. 50PPCh. 7 - Prob. 51PPCh. 7 - Prob. 52PPCh. 7 - Prob. 53PPCh. 7 - Prob. 54PPCh. 7 - Prob. 55PPCh. 7 - Prob. 56PPCh. 7 - Prob. 57PPCh. 7 - Prob. 58PPCh. 7 - Prob. 59PPCh. 7 - Prob. 60PPCh. 7 - Prob. 61PPCh. 7 - Prob. 64PPCh. 7 - Indicate whether you would use NaOEt or tBuOK to...Ch. 7 - Prob. 68PPCh. 7 - Draw a plausible mechanism for each of the...Ch. 7 - Prob. 70PPCh. 7 - Prob. 71PPCh. 7 - Prob. 72PPCh. 7 - Prob. 73PPCh. 7 - Prob. 74PPCh. 7 - Prob. 77PPCh. 7 - Prob. 78PPCh. 7 - Prob. 81ASPCh. 7 - Prob. 87ASPCh. 7 - Prob. 90ASPCh. 7 - Prob. 91IPCh. 7 - Prob. 92IPCh. 7 - Prob. 93IPCh. 7 - Prob. 94IPCh. 7 - Prob. 95IPCh. 7 - Prob. 96IPCh. 7 - Prob. 97IPCh. 7 - Prob. 98IPCh. 7 - Prob. 99IPCh. 7 - Prob. 100IPCh. 7 - Prob. 101IPCh. 7 - Prob. 102IPCh. 7 - Prob. 103IPCh. 7 - Prob. 105IPCh. 7 - Prob. 106IPCh. 7 - Prob. 107IPCh. 7 - Prob. 109IPCh. 7 - Prob. 110CPCh. 7 - Prob. 112CPCh. 7 - Prob. 114CP
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
- Assuming that no equilibria other than dissolution are involved, calculate the molar solubility of each of the following from its solubility product: (a) KHC4H4O6arrow_forwardAnswer the following by equation 1. reactio of CH3MgBr with Acetone [CH3COCH3] 2. acetal formation reaction of acetaldehyde [CH3CHO] 3. preparation of ethylmethylether [C2H5OCH3] 4. the acidity of the carboxylic acid depends and affected by the substitutions on the rest of the acid molecule: draw 2 structures of acids to show the different effects on acidity by different subsarrow_forwardConsider the reaction sequence below to answer the following questions: 0 0 0 0 0 1. NaOEt, EtOH H3O* OEt OET 2 PhCH Br heat Ph + EtOH + CO₂ CHh B C A A. The starting material A in this reaction sequence is called a a. ẞ-keto ester b. a-carboethoxy ketone C. malonic ester d. acetoacetic ester B. Conversion of A into B is a type of reaction termed a. an acylation b. an enolation C. d. an alkylation a phenylation f reactionsarrow_forward
- 1. Refer to the compounds below to answer the following questions: CO₂Et 0 C. H O O₂N-CH2-C-CH3 0 OEt || 111 A. Indicate all the acidic hydrogens in Compounds I through IV. IV B. Indicate which hydrogens in Compound II are the most acidic. Explain your answer C. Choose the most acidic compound from Compounds I - IV. Explain your choice.arrow_forwardShow how you would accomplish the following transformations. More than one step may be required. ow all reagents and all intermediate structures [one ONLY] A. H Br H CH3 NHz CH3 CH3 B. CH3CH2C-Br CH3CH2C-CN CH3 CH3.arrow_forwardShow how you would accomplish the following transformations. More than one step may be required. now all reagents and all intermediate structures [one ONLY] A. H Br H CH3 NHz CH3 CH3 B. CH3CH2C-Br CH3 CH3CH2C-CN CH3arrow_forward
- Can I please get help with this?arrow_forwardC. I, II, III Consider the reaction sequence below to answer the following questions: 0 0 1. NaOEt, EtOH ΕΙΟ OEt 2 Compound X CO₂Et NaOEt, EtOH CO₂Et Br Compound Y A Compound Z A. Compound X, diethyl propanedioate, is more commonly known as a. ethyl acetoacetate acetoacetic ester b. C. oxalic ester d. malonic ester B. Write the complete stepwise mechanism for the conversion of Compound X into Compound Y. Show all electron flow with arrows and draw all intermediate structures.arrow_forwardDiethyl malonate can be prepared by the following reaction sequence. Draw the structures of each of the missing intermediates in the boxes provided EtO 0 H3C 11 C 1. Br₂ PBr OH 2 H₂O 010 0 CH3CH₂OH C CH2 OEt Ha CH3CH2OH на NaCN H₂SO4 NC H₂O, heat CH2 OCH2CH3arrow_forward
- Show how you would accomplish each of the following transformations. More than one step may be quired. Show all reagents and all intermediate structures. [three only] A. 0 CH3 B. C. D. H 0 0 OCH 3 CH₂CO₂CH2CH3 H3C ➤ HN C NO₂ Clarrow_forwardChoose the BEST reagent for carrying out each of the following conversions. A. CO₂CH3 CO₂CH3 0 CO₂H a. LiAlH4, ether C. CrO3, pyridine B. 0 H a. C. NaBH4, ethanol NaOH, H2O CO₂H OH HD b. NaBH4, ethanol d. H₂/Pd CH₂OH b. CH₂PPh3 d. All of the abovearrow_forwardWrite the complete stepwise mechanism for the acid-catalyzed hydrolysis of the following amide to yield mandelic acid. Show all electron flow with arrows and draw the structures of all intermediate species. OH H-OH₂ CnH2 :0: OH C OH + NH4 10: The purpose of the acid catalyst in the hydrolysis of an amide is: to enhance the electrophilicity of the amide carbonyl carbon a. to enhance the nucleophilicity of the water molecule b. C. to enhance the electrophilicity of the water molecule d. to shift the equilibrium of the reactionarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning