EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Question
Chapter 9.13, Problem 44P
(a)
Interpretation Introduction
Interpretation:
From the compounds given below one which is more reactive in SN1 reaction is to be identified.
Concept Introduction:
If
(b)
Interpretation Introduction
Interpretation:
The product formed by SN1 reaction of the above compounds when ethanol is used as the solvent is to be identified.
Concept Introduction:
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Decide which of the following molecules these statements belong to.
Each molecule is only used as answer once.
Br
A
B
Br
C
Br
D
This molecule has the highest reaction rate of
[Choose ]
all in an SN2 reaction.
[Choose ]
This molecule has the highest reaction rate in an
D
SN1 reaction.
A
This molecule can neither react by an SN1 nor
an SN2 mechanism.
E
B
This molecule can react by an SN1, E1 or E2
mechanism but will never react by an SN2
mechanism.
C
F
This moelcule can react my an SN2 or E2
mechanism but will not react by an SN1 or E1
mechanism.
[Choose]
This molecule reacts rapidly by either an SN1 or
[Choose ]
an SN2 mechanism.
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Br
Br
E
F
Br
Which of these will be the most likely to rearrange during an SN1 reaction.
TsO
Br
Br
5) Consider the two E2 reactions above.
Br
Br
NaOH
DMF
heat
NaOH
DMF
heat
a. What are the major products for each reaction?
b. What is the mechanism for each reaction?
c. Which reaction would be faster and why? Use words like "transition-state,
intermediate and/or reactant/product stability" in your justification. Draw the
reaction coordinate diagram for both to assist in your explanation.
Chapter 9 Solutions
EBK ORGANIC CHEMISTRY
Ch. 9.1 - Prob. 3PCh. 9.1 - Does increasing the energy barrier for an SN2...Ch. 9.1 - Rank the following alkyl bromides from most...Ch. 9.1 - Prob. 8PCh. 9.2 - Prob. 9PCh. 9.2 - Prob. 10PCh. 9.2 - Prob. 11PCh. 9.2 - Prob. 12PCh. 9.2 - Which substitution reaction lakes place more...Ch. 9.2 - Prob. 15P
Ch. 9.2 - Prob. 17PCh. 9.3 - Prob. 18PCh. 9.4 - Prob. 19PCh. 9.5 - Draw the configuration(s) of the substitution...Ch. 9.5 - Which of the following reactions take place more...Ch. 9.7 - Prob. 22PCh. 9.7 - Prob. 23PCh. 9.7 - Prob. 24PCh. 9.7 - Prob. 25PCh. 9.8 - Four alkenes are formed from the E1 reaction of...Ch. 9.8 - If 2-fluoropentane could undergo an E1 reaction,...Ch. 9.8 - Prob. 28PCh. 9.8 - Propose a mechanism for the following reaction:Ch. 9.9 - Prob. 30PCh. 9.9 - What percentage of the reaction described in...Ch. 9.10 - Prob. 33PCh. 9.10 - Prob. 35PCh. 9.11 - Why do cis-1-bromo-2-ethylcyclohexane and...Ch. 9.11 - Which isomer reacts more rapidly in an E2...Ch. 9.11 - Prob. 38PCh. 9.12 - Prob. 39PCh. 9.12 - Prob. 40PCh. 9.12 - Prob. 41PCh. 9.12 - Explain why only a substitution product and no...Ch. 9.12 - a. Explain why 1-bromo-2,2-dimethylpropane has...Ch. 9.13 - Prob. 44PCh. 9.13 - Prob. 45PCh. 9.13 - What products will be obtained from the El...Ch. 9.13 - Prob. 47PCh. 9.13 - Prob. 48PCh. 9.13 - Prob. 49PCh. 9.13 - Why is a cumulated diene not formed in the...Ch. 9.13 - What product is obtained when the following...Ch. 9.13 - What products are formed from the following...Ch. 9.14 - Prob. 54PCh. 9.14 - Prob. 55PCh. 9.14 - Prob. 56PCh. 9.14 - Prob. 58PCh. 9.14 - Under which of the following reaction conditions...Ch. 9.15 - A small amount of another organic product is...Ch. 9.15 - What is the best way to prepare the following...Ch. 9.15 - Prob. 62PCh. 9.15 - What products (including stereoisomers, if...Ch. 9.16 - After a proton is removed from the OH group, which...Ch. 9.16 - Prob. 65PCh. 9.17 - Prob. 66PCh. 9 - Prob. 1PCh. 9 - Methoxychlor is an insecticide that was intended...Ch. 9 - Prob. 67PCh. 9 - Prob. 68PCh. 9 - Prob. 69PCh. 9 - Prob. 70PCh. 9 - Prob. 71PCh. 9 - Prob. 72PCh. 9 - Starting with cyclohexene, how can the following...Ch. 9 - Prob. 74PCh. 9 - The pKa of acetic acid in water is 4.76. What...Ch. 9 - Prob. 76PCh. 9 - Prob. 77PCh. 9 - Prob. 78PCh. 9 - Prob. 79PCh. 9 - Prob. 80PCh. 9 - Prob. 81PCh. 9 - Prob. 82PCh. 9 - Draw the major product obtained when each of the...Ch. 9 - Prob. 84PCh. 9 - a. Indicate how each of the following factors...Ch. 9 - Prob. 86PCh. 9 - A chemist wanted to synthesize the...Ch. 9 - Prob. 88PCh. 9 - Prob. 89PCh. 9 - Prob. 90PCh. 9 - Prob. 91PCh. 9 - Starting with an alkyl halide, how could the...Ch. 9 - Indicate which species in each pair gives a higher...Ch. 9 - Prob. 94PCh. 9 - Rank the following from most reactive to least...Ch. 9 - For each of the following alkyl halides, indicate...Ch. 9 - Prob. 97PCh. 9 - When 2-bromo-2,3-dimethylbutane reacts with a...Ch. 9 - Prob. 100PCh. 9 - When the following compound undergoes solvolysis...Ch. 9 - cis-1-Bromo-4-tert-butylcyclohexane and...Ch. 9 - Draw the substitution and elimination products.Ch. 9 - tert-Butyl chloride undergoes solvolysis in both...Ch. 9 - Prob. 105PCh. 9 - Prob. 106PCh. 9 - In which solventethanol or diethyl etherwould the...Ch. 9 - Prob. 108PCh. 9 - Two bromoethers are obtained from the reaction of...Ch. 9 - Prob. 110PCh. 9 - Prob. 111PCh. 9 - Prob. 112PCh. 9 - Which of the following hexachlorocyclohexanes is...Ch. 9 - Explain why the rate of the reaction of...Ch. 9 - Prob. 115PCh. 9 - Two elimination products are obtained from the...Ch. 9 - Draw the structures or the product of the obtained...Ch. 9 - How could you prepare the following compounds from...Ch. 9 - cis-4-Bromocyclohexanol and...Ch. 9 - Prob. 120PCh. 9 - Propose a mechanism for the following reaction:Ch. 9 - Prob. 122PCh. 9 - Prob. 123PCh. 9 - Prob. 124PCh. 9 - Prob. 125PCh. 9 - Predict the product for the following reaction and...Ch. 9 - Prob. 127PCh. 9 - Prob. 128PCh. 9 - When equivalent amounts of methyl bromide nod...Ch. 9 - Prob. 130PCh. 9 - The reaction of chloromethane with hydroxide ion...
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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
- For each of the following reactions indicate whether the major products will be the result of an SN1. SN2, E1 or E2 reaction process. (Note if required the same answer can be used more than once. i.e. there may be two "SN1" isomers or "E2" reactions, etc.) Choose carefully. KO'Bu H. Br 1. SN1 Me Me 2. SN2 HO H Heat "Me 3. E1 Me 4. E2 HO13arrow_forwardPart A 1. Explain why 1-bromo-2,2-dimethylpropane has difficulty undergoing both SN2 and SN1 reactions. 2. Can it undergo E2 and E1 reactions? Match the words in the left column to the appropriate blanks in the sentences on the right. Make certain each sentence is co Submit can SN1 SN2 secondary tertiary primary E2 hydrogen cannot E1 carbon Previous Answers Request Answer X Incorrect; Try Again; 3 attempts remaining Reset Help 1. The bulky tert-butyl substituent blocks the back side of the carbon bonded to the bromine to nucleophilic attack, making an SN2 reaction difficult. An SN1 reaction cannot occur because it would require the formation of an unstable primary carbocation. 2. It cannot undergo an E2 reaction, because the B-carbon is not bonded to a hydrogen. It cannot undergo an E1 reaction, because that would require the formation of a tertiary carbocation.arrow_forwarda) Which student’s reaction (Danny or Claire) has provided a single elimination isomer? b) Draw all the elimination isomers obtained from both students’ reactions. c) Which of the dienes drawn (by you) in question 3b is the most stable? Circle that diene above.arrow_forward
- Which is fastest in an SN1 reaction? Why? Explain with structures, logic, a potential energy diagram, and complete sentences. Clarrow_forwardWhy is this an E1/Sn1 reaction instead of just Sn1?arrow_forward3. For each reaction, determine all reasonable products that would form. • Underneath each product label if the product is from an Sn1, Sn2, E1, or E2 reaction. In reactions that give both elimination and substitution products, determine whether there will be more elimination or substitution. Br • • For any E1 or Sn1, show any reasonable products of rearrangements. Circle the major product in each reaction If more than one elimination product is formed for a reaction, place a box around the one that is the major elimination product. H I H-C-H CI ax OTS Br Br A Br Na to Хон X DMSO Хон NaOH DMSO OH OHarrow_forward
- For Sn1 and Sn2 reactions, explain why one type of carbon should react faster than others.arrow_forwardThe molecule, 2-bromo-1,3-diethyl-1,4-dimethylcyclohexane undergoes an SN1/E1 reaction in the solvent ethanol. i) Draw the intermediate resulting from the first step of this reaction. ii) Draw the two most favorable intermediates resulting from carbonation iii) From the intermediate(s) in (ii) draw all the possible E1 products and circle the product(s) that is(are) most favorable. iv) Name the most favorable product(s). v) Draw an SN1 product from an intermediate in (ii).arrow_forward2. Which SN1 reaction would you expect to occur more rapidly? Explain a. (CH3)3CC1+ H₂O → (CH3)3COH + HC1 b. (CH3)3CBr + H₂O → (CH3)3COH + HBrarrow_forward
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