Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Question
Chapter 7.15, Problem 7.28P
(a)
Interpretation Introduction
To determine: The product of the elimination reaction between
Interpretation: The product of the elimination reaction between
Concept introduction: The elimination reaction is the organic reaction in which two substituents are removed from the organic molecule in one step or two steps. The two mechanisms of the elimination reaction are the E1 and E2 mechanisms.
In E2 mechanism, the elimination takes place in one step.
According to the Zaitsev rule, the formation of
(b)
Interpretation Introduction
To determine: The product of the elimination reaction between
Interpretation: The product of the elimination reaction between
Concept introduction: The elimination reaction is the organic reaction in which two substituents are removed from the organic molecule in one step or two steps. The two mechanisms of the elimination reaction are E1 and E2 mechanism.
In E2 mechanism, the elimination takes place in one step.
According to the Zaitsev rule, the formation of alkene occurs by the elimination of the hydrogen from the carbon that has less hydrogen.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
What product do you expect from the reaction of butan-2-one with hydroxylamine, NH₂O?
a.
O b.
O c.
O d.
NH
||
CH3-CH₂CH₂C-CH3
NOH
||
CH3-CH₂CH₂C-CH3
NHOH
I
CH3-CH₂CH₂CH-CH3
NOH
||
CH3CH₂C-CH3
Choose the best reagents to
complete the reaction shown below.
A
B
C
E
D
HO
о
O=
OH
RCO₂H
1. OsO4 (catalytic)
2. NMO
1. KMnO4, OH- (warm)
2. H₂O*
MCPBA
2. H3O+
1. Hg(OAc)2, H2O
E
2. NaBH4, NaOH
Q
Q
Heck reactions take place with alkynes as well as alkenes. The following conversion involves an intramolecular Heck reaction followed by an
intermolecular Heck.
Work out the reaction sequence on a separate sheet of paper, and then draw the structure of the palladium-containing intermediate A.
1% mol Pd(OAc)₂2
CO₂Me
4% mol Ph P
CH₂CN
A
(1 ring)
C
(2 rings)
(2 rings)
• Consider E/Z stereochemistry of alkenes.
• You do not have to explicitly draw H atoms.
• Do not include lone pairs in your answer. They will not be considered in the grading.
• Use R1 to represent the palladium complex. The R group tool is located in the charges and lone pairs drop-down menu.
0-
✪
Sn [F
MeO₂C
Chapter 7 Solutions
Organic Chemistry (9th Edition)
Ch. 7.3A - Prob. 7.1PCh. 7.3A - Prob. 7.2PCh. 7.3B - Draw five more compounds of formula C4H6NOC1.Ch. 7.3B - For each of the following molecular formulas,...Ch. 7.4 - Give the systematic (IUPAC) names of the following...Ch. 7.5B - The following names are all incorrect. Draw the...Ch. 7.5B - Prob. 7.8PCh. 7.5B - a. How many stereogcmc double bonds are in...Ch. 7.6 - Teflon-coated frying pans routinely endure...Ch. 7.7B - Prob. 7.11P
Ch. 7.8B - Use the data in Table7-2 to predict the energy...Ch. 7.8C - Prob. 7.13PCh. 7.8E - Explain why each of the following alkenes is...Ch. 7.8F - Prob. 7.15PCh. 7.10 - Prob. 7.16PCh. 7.10A - SN1 substitution and E1 elimination frequently...Ch. 7.10C - Prob. 7.18PCh. 7.10C - Prob. 7.19PCh. 7.10C - Prob. 7.20PCh. 7.11 - Prob. 7.21PCh. 7.11 - Prob. 7.22PCh. 7.12 - Prob. 7.23PCh. 7.12 - Prob. 7.24PCh. 7.13 - Prob. 7.25PCh. 7.14B - Prob. 7.26PCh. 7.14B - Make models of the blowing compounds, and predict...Ch. 7.15 - Prob. 7.28PCh. 7.15 - Prob. 7.29PCh. 7.15 - Prob. 7.30PCh. 7.15 - Prob. 7.31PCh. 7.16 - Predict the major and minor elimination products...Ch. 7.17B - Predict the products and mechanisms of the...Ch. 7.18 - Propose mechanisms for the following reactions.Ch. 7.18 - Prob. 7.35PCh. 7.19B - The dehydrogenation of butane to trans-but-2-ene...Ch. 7.19B - Prob. 7.37PCh. 7.19B - Prob. 7.38PCh. 7.19B - Prob. 7.39PCh. 7 - Prob. 7.40SPCh. 7 - Prob. 7.41SPCh. 7 - Prob. 7.42SPCh. 7 - Prob. 7.43SPCh. 7 - Prob. 7.44SPCh. 7 - Prob. 7.45SPCh. 7 - Prob. 7.46SPCh. 7 - The energy difference between cis- and...Ch. 7 - Prob. 7.48SPCh. 7 - Prob. 7.49SPCh. 7 - Prob. 7.50SPCh. 7 - What halides would undergo E2 dehydrohalogenation...Ch. 7 - Prob. 7.52SPCh. 7 - Prob. 7.53SPCh. 7 - Write a balanced equation for each reaction,...Ch. 7 - Prob. 7.55SPCh. 7 - Using cyclohexane as your starting material, show...Ch. 7 - Show how you would prepare cyclopentene from each...Ch. 7 - Prob. 7.58SPCh. 7 - E1 eliminations of alkyl halides are rarely useful...Ch. 7 - Prob. 7.60SPCh. 7 - Propose mechanisms for the following reactions....Ch. 7 - Prob. 7.62SPCh. 7 - Prob. 7.63SPCh. 7 - Prob. 7.64SPCh. 7 - Prob. 7.65SPCh. 7 - Prob. 7.66SPCh. 7 - Prob. 7.67SPCh. 7 - Prob. 7.68SPCh. 7 - Prob. 7.69SPCh. 7 - Explain the dramatic difference in rotational...Ch. 7 - One of the following dichloronorbornanes undergoes...Ch. 7 - A graduate student wanted to make...Ch. 7 - Prob. 7.73SPCh. 7 - Prob. 7.74SPCh. 7 - Prob. 7.75SPCh. 7 - Prob. 7.76SP
Knowledge Booster
Similar questions
- 2. Predict the major product of the following EAS reactions. Assume only one equivalent of reagents. 1. CI OCH3 BCI3 OCH3 2. Zn(Hg) HCI A NH2 Cl2 BCI3 HNO3 H2SO4 Br fuming H2SO4 CI FeClaarrow_forwardWhich is the MAJOR product of the following reaction? Et 1) BH3:THF 2) H2O2, NaOH Which of the following best describes a key step in the mechanism for the reaction below? HO ... CH3 -CH3 dihydroxylation + en H3C- H3C- HO. electrophilic addition reaction to form a carbocation intermediate B nucleophilic attack by an alkene to form a cyclic (epoxide) intermediate elimination reaction by abstraction of a beta-hydrogen D free-radical substitution at the carbonyl carbon Which alkene will produce the HIGHEST yield of the alkyl halide below? Br. alkene HBr |arrow_forward6. Provide the structure for the major product in the following reactions. b. P f. OH g. Lia * Oia ملی CI 1. SOCI₂, pyr. 2. to Br 2 1. LIAIH4 (xs) 2. H₂O 1. LIAI(OR) 3H 2. H₂O 2. NH₂ Et₂CuLi 1. EtMgBr (xs) 2. H₂O 1. Mg 2. CO₂ 3. H* 4. SOCI₂, pyr 1. [H], NaBH3CN, EtNH₂ CI pyridinearrow_forward
- Ql- Arrange the following carbonium ion as more stable. Why? Me Me „Me A C Q2- Choose the substituted group that makes the following reaction faster. Why? X- CH2 H X- ососн, OR COOCH} Y= NH2 OR NO2 Q3- Which of the following compounds give the highest yield when reacting with a carbonyl compound. Why? NH 2 NH2 NH2 Me Me Me OR OR NO 2 NO2 NO2arrow_forwardAlcohols are important for organic synthesis, especially in situations involving alkenes. The alcohol might be the desired product, or the OH group might be transformed into another functional group via halogenation, oxidation, or perhaps conversion to a sulfonic ester derivative. Formation of an alcohol from an alkene is particularly powerful because conditions can be chosen to produce either the Markovnikov or non-Markovnikov product from an unsymmetrical alkene. Using your reaction roadmap as a guide, show how to convert 4-methyl-1-pentene into 5-methylhexanenitrile. You must use 4-methyl-1-pentene and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.arrow_forward2-Methoxy-2-methylpropane on heating with HBr gives : A 2-Methylpropan-2-ol and Bromomethane Methanol and 2-Bromo-2-methylpropane 2-Methylpropan-1-ol and bromomethane D Methoxymethane and Propylbromidearrow_forward
- 3. Predict the product for each of the following reactions and draw a stepwise mechanism to account for the transformation. Why are the outcomes different? 1. NaH 2. Br2 1. LDA 2. Br2arrow_forward2. Consijder the reactiojn scheme below a. Draw the major product of this reaction. Show clearly (using wedge-and-dash lines) all stereoisomers formed under these reaction conditions. 1. BH3:THF 2. H2O2, NaOH b. What is the stereochemical relationship between the different stereoisomer products you drew in part 2a.?arrow_forwardWhich organic starting material is needed to complete the following reaction? H₂C A B C D ? H₂ A 1) (CF3COO)₂Hg, CH₂CH₂OH 2) NaBH4 CH3 H₂C B =CH₂ H3C H3C OH T CH H₂ с H₂ F1₂ OCH₂CH3 I CH CH3 OCH₂CH3 CH H3C CH3 H₂ D OCH₂CH3 T .CH CH3arrow_forward
- Predict the major product of the reaction. starting material O А. B. D. Е. OH OH 1. BH3 2. NaOH, H. H2O ОН OH H OH enol intermediate productarrow_forwardPredict the major products of each of the following reactions. CH3 Br,/CCI4 HO a. e. CH3 HNO3 Br2 f. OMe Br,/CCI4 С. Br2 g. NO2 OMe H2SO4 d. high Temp OMe b.arrow_forwardFrom the choices provided below, list the reagent(s) in order that will yield the following transformation. Br Reagents available a. HIO4 b. HC C Na+ c. CH3ONa+, CH, OH k. RCO, H d. NaCN e. CH3CH₂S Na+ f. H₂O+ g. H₂O h. H₂ CrO4 Your answer: i. H₂SO4, H₂O j. potassium tert-butoxide I. HN(CH, CH3 ) m. NBS, hv n. OsO4, H₂O2 NaOH O. p. pyridinium chlorochromate (PCC) List your answer as a series of letters in the order the reagents are used (with no commas separating them). No more than four steps are required for this synthesis. Use the minimum number of steps possible. Reagents may be used more than once in subsequent steps. For example, "dop". Note: The order in which you list your letters matters!arrow_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