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a)
Interpretation:
The given molecule has to be prepared by using nucleophilic substitution reaction.
Concept introduction:
SN1 reaction:
The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.
Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.
Primary alcohol is less stable therefore it won’t undergo SN1substitution reaction.
SN2 reaction:
The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid, the bromine atom attacks back side of the carbon atoms in simultaneous manner and which is bearing alcohol group which yield the corresponding product.
Example:
Alcohol is reaction with tosyl chloride in pyridine which provides retention of configuration of tosylated compound. This tosylated compound is further reaction with sodium methoxide which undergoes again SN2 type of reaction, the methoxide ion attacks the carbon atom through the back side and provides Inverse configuration of methoxy compound. This is shown below,
SN2 reaction is second order
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Answer to Problem 45AP
The reaction is given below,
Explanation of Solution
Given information:
The product of the reaction is given below,
The reaction is given below,
The sodium amide is acts as a base and it abstract the highly acidic proton from propylene gives carbanion, this carbanion react with 2-bromo propane gives the corresponding product.
The given molecule is prepared by using nucleophilic substitution reaction.
b)
Interpretation:
The given molecule has to be prepared by using nucleophilic substitution reaction.
Concept introduction:
SN1 reaction:
The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.
Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.
Primary alcohol is less stable therefore it won’t undergo SN1substitution reaction.
SN2 reaction:
The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid, the bromine atom attacks back side of the carbon atoms in simultaneous manner and which is bearing alcohol group which yield the corresponding product.
Example:
Alcohol is reaction with tosyl chloride in pyridine which provides retention of configuration of tosylated compound. This tosylated compound is further reaction with sodium methoxide which undergoes again SN2 type of reaction, the methoxide ion attacks the carbon atom through the back side and provides Inverse configuration of methoxy compound. This is shown below,
SN2 reaction is second order reaction, the rate of the reaction is depending on the both substrate and nucleophiles.
![Check Mark](/static/check-mark.png)
Answer to Problem 45AP
The reaction is given below,
Explanation of Solution
Given information:
The product of the reaction is given below,
The reaction is given below,
The sodium tertiary butoxide is acts as a base and it react with methyl bromide gives the corresponding ether product.
The given molecule is prepared by using nucleophilic substitution reaction.
c)
Interpretation:
The given molecule has to be prepared by using nucleophilic substitution reaction.
Concept introduction:
SN1 reaction:
The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.
Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.
Primary alcohol is less stable therefore it won’t undergo SN1substitution reaction.
SN2 reaction:
The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid, the bromine atom attacks back side of the carbon atoms in simultaneous manner and which is bearing alcohol group which yield the corresponding product.
Example:
Alcohol is reaction with tosyl chloride in pyridine which provides retention of configuration of tosylated compound. This tosylated compound is further reaction with sodium methoxide which undergoes again SN2 type of reaction, the methoxide ion attacks the carbon atom through the back side and provides Inverse configuration of methoxy compound. This is shown below,
SN2 reaction is second order reaction, the rate of the reaction is depending on the both substrate and nucleophiles.
![Check Mark](/static/check-mark.png)
Answer to Problem 45AP
The reaction is given below,
Explanation of Solution
Given information:
The product of the reaction is given below,
The reaction is given below,
n-butyl bromide undergoes nucleophilic substitution reaction with cyanide (sodium cyanide) gives the corresponding cyanide product.
The given molecule is prepared by using nucleophilic substitution reaction.
d)
Interpretation:
The given molecule has to be prepared by using nucleophilic substitution reaction.
Concept introduction:
SN1 reaction:
The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.
Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.
Primary alcohol is less stable therefore it won’t undergo SN1substitution reaction.
SN2 reaction:
The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid, the bromine atom attacks back side of the carbon atoms in simultaneous manner and which is bearing alcohol group which yield the corresponding product.
Example:
Alcohol is reaction with tosyl chloride in pyridine which provides retention of configuration of tosylated compound. This tosylated compound is further reaction with sodium methoxide which undergoes again SN2 type of reaction, the methoxide ion attacks the carbon atom through the back side and provides Inverse configuration of methoxy compound. This is shown below,
SN2 reaction is second order reaction, the rate of the reaction is depending on the both substrate and nucleophiles.
![Check Mark](/static/check-mark.png)
Answer to Problem 45AP
The reaction is given below,
Explanation of Solution
Given information:
The reaction is given below,
The reaction is given below,
Ethyl bromide undergoes nucleophilic substitution reaction with cyanide (sodium cyanide) gives the corresponding cyanide product, this cyanide undergoes catalytic reduction using Pt (metal reduction) gives
The given molecule is prepared by using nucleophilic substitution reaction.
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Chapter 11 Solutions
Organic Chemistry
- Don't used hand raiting don't used Ai solutionarrow_forwardHomework: Atomic Structure This homework is due at the beginning of class next lecture period and is worth 6 points. Please place the number of protons and neutrons in the nucleus and then put the number of electrons in the correct shell. Also give the correct atomic mass. Also, state if the atom is an ion (cation or anion). H* 1. Number of protons Number of electrons Number of neutrons Atomic mass 2. 26 13AI +++ Number of protons Number of neutrons Number of electrons Atomic massarrow_forwardDon't used hand raitingarrow_forward
- I need help working this problem out step by step, I was trying to use my example from the txt book but all I know how to do is set it up. I need to be shown step by step as I am a visual learner. Please help me.arrow_forwardDon't used hand raitingarrow_forwardDon't used Ai solution and don't used hand raitingarrow_forward
- & Calculate the molar enthalpy of combustion (A combH) of 1.80 g of pyruvic acid (CH3COCOOH; 88.1 g mol-1) at 37 °C when they are combusted in a calorimeter at constant volume with a calorimeter constant = 1.62 kJ °C-1 and the temperature rose by 1.55 °C. Given: R = 8.314 J mol −1 °C-1 and the combustion reaction: AN C3H4O3 + 2.502(g) → 3CO2(g) + 2H2O(l)arrow_forwardAn unknown salt, AB, has the following precipitation reaction:A+(aq) + B-(aq) ⇌ AB(s) the K value for this reaction is 4.50 x10-6. Draw a model that represents what will happen when 1.00 L each of 1.00 M solution of A+(aq) and 1.00M solution of B-(aq) are combined.arrow_forward5. a) Use the rules in Example 4.4 (p. 99) and calculate sizes of octahedral and tetrahedral cavities in titanium and in zirconium. Use values for atomic radii given in Fig. 9.1 (p.291). (3 points) b) Consider the formation of carbides (MC) of these metals. Which metal is able to accommodate carbon atoms better, and which cavities (octahedral or tetrahedral) would be better suited to accommodate C atoms into metal's lattice? (4 points)arrow_forward
- 2. Read paragraph 3.4 in your textbook ("Chiral Molecules"), and explain if Cobalt(ethylenediamine) 33+ shown in previous problem is a chiral species. If yes, draw projections of both enantiomers as mirror images, analogous to mirror projections of hands (below). Mirror (4 points)arrow_forward3. Borane (BH3) belongs to D3h point group. Consider the vibrational (stretching) modes possible for B-H bonds under D3h symmetry. Using the methods we used in class, construct the reducible representation I, and break it down into irreducible representations using the character table provided. Sketch those modes, indicate whether they are IR-active. (6 points) D3h E 2C3 3C2 σh 283 30% A₁' 1 1 1 1 1 1 x² + y², z² 1 -1 1 1 -1 R₂ E' 2 0 2 0 (x, y) (x² - y², xy) " A₁" 1 1 -1 A2" 1 -1 -1 1 Z E" 2 -1 0 -2 1 0 (Ry, Ry) (xz, yz)arrow_forward1. List all the symmetry elements, and assign the compounds to proper point groups: a) HCIBrC-BrCIH Cl Br H (2 points) H Br b) Pentacarbonylmanganese(I)bromide Br OEC-Mn-CEO 00- c) Phenazine (aromatic molecule, with delocalized bonding) 1 d) Cobalt(ethylenediamine)33+ (just the cation) 3+ H₂N H₂ .NH2 (CI)3 NH2 H2 H₂N. (2 points) (2 points) (2 points)arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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