Organic Chemistry (Binghampton University)
16th Edition
ISBN: 9781308795010
Author: Carey
Publisher: MCG CUSTOM
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Textbook Question
Chapter 10.4, Problem 8P
How many constitutionally isomeric monochlorination products are possible from each of the following?
a)
b)
c)
d)
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INSTRUCTIONS: Choose from the options A-E and explain briefly by illustrations the chemistry behind each answer.
Preamble: A reaction flask contains a 2-bromopentane in an ethanolic solution of sodium ethoxide at room temperature and results in the formation of two olefinic products.
Predict the products that would be formed from such a reaction
A. 1-pentene (80%) and 2-pentene (20%)
B. 1-pentene (20%) and 2-pentene (80 %)
C. 1-pentene (50 %) and 2-pentene (50 %)
D. 1-pentene (0 %) and 2-pentene (100 %)
E. 1-pentene (100 %) and 2-pentene (0 %)
2. What reaction pathway is followed by the reaction above?
A. E1 dehydrohalogenation
B. E2 dehydrohalogenation
C. SN1 dehydrohalogenation
D. SN2 dehydrohalogenation
E. A mixture of E1 and E2 pathways
3. What is responsible for the formation of different products (major and minor).
A. The different activated complex involved in the mechanism.
B. Bimolecular Nucleophilic substitution reaction
C. Bimolecular Elimination reaction
D. The…
Select the correct statements regarding the reactions of tertiary haloalkanes. *
A- Tertiary haloalkanes form alkenes through both the E1 mechanism and the E2 mechanism.
B- Tertiary haloalkanes react with water to form ethers.
C- A tertiary haloalkane always forms a tertiary carbocation as an intermediate when a substitution reaction occurs.
D- A tertiary haloalkane always forms a tertiary carbocation as an intermediate when an elimination reaction occurs.
When an unsaturated hydrocarbon interacts with acidic KMnO4, the sole organic product is isobutyric acid. Most likely, the unsaturated hydrocarbon is:
a. 4-methyl-2-hexene
b. 2,2-dimethyl-3-hexene
c. 3,4-dimethyl-3-hexene
d. 2,5-dimethyl-3-hexene
e. none of the above
Chapter 10 Solutions
Organic Chemistry (Binghampton University)
Ch. 10.1 - Prob. 1PCh. 10.1 - Prob. 2PCh. 10.2 - Use the data in Table 10.1 to calculate H for the...Ch. 10.3 - Prob. 4PCh. 10.4 - Prob. 5PCh. 10.4 - Prob. 6PCh. 10.4 - Do the arithmetic involved in converting the...Ch. 10.4 - How many constitutionally isomeric...Ch. 10.4 - Prob. 9PCh. 10.5 - Prob. 10P
Ch. 10.5 - Prob. 11PCh. 10.5 - Prob. 12PCh. 10.6 - Prob. 13PCh. 10.7 - Prob. 14PCh. 10.8 - Prob. 15PCh. 10 - Carboncarbon bond dissociation enthalpies have...Ch. 10 - Use the bond dissociation enthalpy data in Table...Ch. 10 - Use the bond dissociation enthalpy data in Table...Ch. 10 - Write the structure of the major organic product...Ch. 10 - Excluding enantiomers, free-radical chlorination...Ch. 10 - Prob. 21PCh. 10 - Prob. 22PCh. 10 - Prob. 23PCh. 10 - Prob. 24PCh. 10 - Compound A (C6H14) gives three different...Ch. 10 - Prob. 26PCh. 10 - Prob. 27PCh. 10 - Prob. 28PCh. 10 - Prob. 29PCh. 10 - Guiding your reasoning by retrosynthetic analysis,...Ch. 10 - (Z)-9-tricosene [(Z)-CH3(CH2)7CH=CH(CH2)12CH3] is...Ch. 10 - Prob. 32PCh. 10 - Prob. 33PCh. 10 - Prob. 34DSPCh. 10 - Prob. 35DSPCh. 10 - Prob. 36DSPCh. 10 - Prob. 37DSPCh. 10 - Prob. 38DSP
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- Compound L undergoes dehydrohalogenation to form hydrogen bromide and 1-methylcyclohexene. What is dehydrohalogenation? State the condition required for dehydrohalogenation. Draw the structural formula of compound L and name L.arrow_forwardChoose the correct answer lettered A-E and explain briefly with illustrations the chemistry behind the answer Preamble: A reaction flask contains a 2-bromopentane in an ethanolic solution of sodium ethoxide at room temperature and results in the formation of two olefinic products. 1.Predict the products that would be formed from such a reaction A.1-pentene (80%) and 2-pentene (20%)B.1-pentene (20%) and 2-pentene (80 %)C.1-pentene (50 %) and 2-pentene (50 %)D.1-pentene (0 %) and 2-pentene (100 %)E.1-pentene (100 %) and 2-pentene (0 %) 2.What reaction pathway is followed by the reaction above?A.E2 dehydrohalogenation B.E1 dehydrohalogenationC.SN1 dehydrohalogenationD.SN2 dehydrohalogenationE.A mixture of E1 and E2 pathways 3.What is responsible for the formation of different products (major and minor).A .The different activated complex involved in the mechanism.B.Bimolecular Nucleophilic substitution reaction C.Bimolecular Elimination reaction D.The presence of sodium ethoxideE.The…arrow_forward1. Using Br2 in C2H4Br2 will result in HBr and ______. a. C2H3Cl3 b. C2H4Cl3 c. C2H2Cl3 d. none of the above 2. How many halogenation are posible in propane? a. 3 b. 8 c. 6 d. 10 3.Sulfonation of pentane will result in ________ and water. a. C5H11SO3H b. C5H12SO3H c. C5H14SO3H d. none of the above 4.Nitration of hexane will result in ________ and water. a. C6H13SO3H b. C6H15NO2 c. C6H13NO2 d. C6H14NO2 5.How many moles of O2 in heating a C12H26 (dodecane) a. 27 b. 37 c. 24 d. none of the abovearrow_forward
- here's the reaction to be used for reference: C2H4 + H2 --> C2H6 1. What type of reaction is involved in C2H4 + H2 --> C2H6? 2. What is C2H4 in the reaction? 3. What is the name of the product in the reaction? a. ethane b. ethene c. ethynearrow_forwardWhich of the following substances does not have a stereogenic carbon? options: methylcyclohexane 1-bromo-1-phenyl ethane 1,2-dichloropropane 2-bromobutane 2-bromopropanalarrow_forwardWhich of the following alkenes is the most suitable to obtain 5-methyl-4-octanol via hydroboration-oxidation reaction? options: This conversion is not possible through hydroboration. This conversion is only possible through hydration reaction. 4-methyl-3-octene 4-methyl-4-octene 5-methyl-2-octene 5-methyl-3-octenearrow_forward
- Answer the following questions based on the reaction scheme below. i) State reagent Q ii) Draw the structural formula for compound R, T, U and Warrow_forwardHow many monochloro substitution products are produced when the alkanes below are chlorinated?arrow_forwardConsider the structure of cyclohexyne, if it undergoes acetylide reaction with NaNH2 and 2 moles of CH3Br, which of the following final product is formed? a. 1,2-methylcyclohexyne HBr b. 1-methylcyclohexyne c. No reactionarrow_forward
- Write a complete chemical equation showing reactants, products, and catalysts needed(if any) for the following reaction and (2) Draw and name the organic compound found inevery reaction.(Use condensed structural formula) (A) Reaction of cis-3,3-Dimethyl-4-propylocta-1,5-diene with two mole of HBr(B) Reaction of trans-1-Bromo-3-chlorocyclopentane with potassium hydroxide(C) Formation of Gilman reagent using isopropyl bromidearrow_forwardA hydrocarbon (Y) partially hydrogenates with the Lindlar’s catalyst to form an alkene. When (Y) undergoes oxidative cleavage with ozone, it yields a single carboxylic acid product. The hydrocarbon (Y) is: a) cyclohexane b) 2-butyne c) 2-hexen-1-ol d) 2-hexynearrow_forwardWhich of the following combination of alcohol and haloalkane will proceed to form an ether? a n-butanol and bromomethane b cyclopentanol and chloroethane c phenol and bromomethane d all of the abovearrow_forward
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