
Concept explainers
What products would you expect from the reaction of 1-bromopropane with each of the following?
(a) NaNH2
(b) KOC(CH3)3
(c) NaI
(d) NaCN
(e) NaC≡CH
(f) Mg, then H2O

a)
Interpretation:
The product has to be identified when 1-bromopropane reacts with the given reagents.
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 SN1 substitution 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.
Elimination reaction: An elimination reaction is removal of two substituents in a molecule and forms alkene. An elimination reaction is one or two-step process which based on the mechanism when two substituents removed from the molecule in single step is called E2 reaction. When two substituents are removed from the molecule in two steps is called E1 reaction.
The Grignard reaction:
Alkyl, vinyl, or aryl-magnesium halides (RMgX) is called as Grignard reagent.
Answer to Problem 50AP
The product of the reaction is given below,
Explanation of Solution
Given information:
The reactant of the reaction is given below,
The product of the reaction is given below,
The sodium amide is acts as a base and it abstract the acidic proton from 1-bromo propane gives carbanion, this carbanion under goes elimination reaction gives propene as a major product.
1-bromo propane undergoes nucleophilic substitution reaction gives propyl amine as a minor product.
The product of the reaction is given when 1-bromopropane reacts with the given reagents.

b)
Interpretation:
The product has to be identified when 1-bromopropane reacts with the given reagents.
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 SN1 substitution 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.
Elimination reaction: An elimination reaction is removal of two substituents in a molecule and forms alkene. An elimination reaction is one or two-step process which based on the mechanism when two substituents removed from the molecule in single step is called E2 reaction. When two substituents are removed from the molecule in two steps is called E1 reaction.
The Grignard reaction:
Alkyl, vinyl, or aryl-magnesium halides (RMgX) is called as Grignard reagent.
Answer to Problem 50AP
The product of the reaction is given below,
Explanation of Solution
Given information:
The reactant of the reaction is given below,
The product of the reaction is given below,
The potassium tertiary butoxide is acts as a base and it abstract the acidic proton from 1-bromo propane gives carbanion, this carbanion under goes elimination reaction gives propene as a major product.
The product of the reaction is given when 1-bromopropane reacts with the given reagents.

c)
Interpretation:
The product has to be identified when 1-bromopropane reacts with the given reagents.
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 SN1 substitution 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.
Elimination reaction: An elimination reaction is removal of two substituents in a molecule and forms alkene. An elimination reaction is one or two-step process which based on the mechanism when two substituents removed from the molecule in single step is called E2 reaction. When two substituents are removed from the molecule in two steps is called E1 reaction.
The Grignard reaction:
Alkyl, vinyl, or aryl-magnesium halides (RMgX) is called as Grignard reagent.
Answer to Problem 50AP
The product of the reaction is given below,
Explanation of Solution
Given information:
The reactant of the reaction is given below,
The product of the reaction is given below,
The sodium iodide is acts as nucleophile, 1-bromo propane undergoes nucleophilic substitution reaction with sodium iodide gives 1-iodo propane.
The product of the reaction is given when 1-bromopropane reacts with the given reagents.

d)
Interpretation:
The product has to be identified when 1-bromopropane reacts with the given reagents.
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 SN1 substitution 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.
Elimination reaction: An elimination reaction is removal of two substituents in a molecule and forms alkene. An elimination reaction is one or two-step process which based on the mechanism when two substituents removed from the molecule in single step is called E2 reaction. When two substituents are removed from the molecule in two steps is called E1 reaction.
The Grignard reaction:
Alkyl, vinyl, or aryl-magnesium halides (RMgX) is called as Grignard reagent.
Answer to Problem 50AP
The product of the reaction is given below,
Explanation of Solution
Given information:
The reactant of the reaction is given below,
The product of the reaction is given below,
The sodium amide is acts as a base and it abstract the acidic proton from 1-bromo propane gives carbanion, this carbanion under goes elimination reaction gives propene as a major product.
1-bromo propane undergoes nucleophilic substitution reaction gives propyl amine as a minor product.
The product of the reaction is given when 1-bromopropane reacts with the given reagents.

e)
Interpretation:
The product has to be identified when 1-bromopropane reacts with the given reagents.
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 SN1 substitution 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.
Elimination reaction: An elimination reaction is removal of two substituents in a molecule and forms alkene. An elimination reaction is one or two-step process which based on the mechanism when two substituents removed from the molecule in single step is called E2 reaction. When two substituents are removed from the molecule in two steps is called E1 reaction.
The Grignard reaction:
Alkyl, vinyl, or aryl-magnesium halides (RMgX) is called as Grignard reagent.
Answer to Problem 50AP
The product of the reaction is given below,
Explanation of Solution
Given information:
The reactant of the reaction is given below,
The product of the reaction is given below,
1-bromo propane undergoes nucleophilic substitution reaction with given alkyne compound gives the corresponding alkyne product.
The product of the reaction is given when 1-bromopropane reacts with the given reagents.

f)
Interpretation:
The product has to be identified when 1-bromopropane reacts with the given reagents.
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 SN1 substitution 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.
Elimination reaction: An elimination reaction is removal of two substituents in a molecule and forms alkene. An elimination reaction is one or two-step process which based on the mechanism when two substituents removed from the molecule in single step is called E2 reaction. When two substituents are removed from the molecule in two steps is called E1 reaction.
The Grignard reaction:
Alkyl, vinyl, or aryl-magnesium halides (RMgX) is called as Grignard reagent.
Answer to Problem 50AP
The product of the reaction is given below,
Explanation of Solution
Given information:
The reactant of the reaction is given below,
The product of the reaction is given below,
1-bromo propane reaction with magnesium gives Grignard reagent and it undergoes hydrolysis gives propane.
The product of the reaction is given when 1-bromopropane reacts with the given reagents.
Want to see more full solutions like this?
Chapter 11 Solutions
Organic Chemistry - With Access (Custom)
- Provide the correct IUPAC name for the compound shown here. Reset cis- 5- trans- ☑ 4-6- 2- 1- 3- di iso tert- tri cyclo sec- oct but hept prop hex pent yl yne ene anearrow_forwardQ6: Predict the major product(s) for the following reactions. Note the mechanism (SN1, SN2, E1 or E2) the reaction proceeds through. If no reaction takes place, indicate why. Pay attention to stereochemistry. NaCN DMF Br σ Ilm... Br H Br H H NaCN CH3OH KOtBu tBuOH NaBr H₂O LDA Et2O (CH3)2CHOH KCN DMSO NaOH H₂O, A LDA LDA Systemarrow_forwardQ7: For the following reactions, indicate the reaction conditions that would provide the indicated product in a high yield. Note the major reaction pathway that would take place (SN1, SN2, E1, or E2) Note: There may be other products that are not shown. There maybe more than one plausible pathway. Br H3C OH H3C CI ... H3C SCH2CH3 CI i SCH2CH3 ཨ་ Br System Settarrow_forward
- Q2: Rank the compounds in each of the following groups in order of decreasing rate of solvolysis in aqueous acetone. OSO2CF3 OSO2CH3 OH a. b. CI Brarrow_forwardох 4-tert-butyl oxy cyclohex-1-ene Incorrect, 1 attempt remaining The systematic name of this compound classifies the -OR group as a substituent of the hydrocarbon, which is considered the principal functional group. The ether substituent is named with the suffix 'oxy'. The general format for the systematic name of a hydrocarbon is: [prefix/substituent] + [parent] + [functional group suffix] Substituents are listed in alphabetical order. Molecules with a chiral center will indicate the absolute configuration at the beginning of its name with the R and S notation.arrow_forward5. Compressibility (6 points total). The isothermal compressibility is a measure of how hard/easy it is to compress an object (how squishy is it?) at constant temperature. It is др defined as Br=-()=-(200²)T' (a) You might wonder why there is a negative sign in this formula. What does it mean when this quantity is positive and what does it mean when this quantity is negative? (b) Derive the formula for the isothermal compressibility of an ideal gas (it is very simple!) (c) Explain under what conditions for the ideal gas the compressibility is higher or lower, and why that makes sense.arrow_forward
- 19. (3 pts) in Chapter 7 we will see a reaction of halocyclohexanes that requires that the halogen occupy an axial position with this in mind, would you expect cis-1-bromo-3-methylcyclohexane or trans-1-bromo-3-methylcyclohexane to be more reactive in this reaction? Briefly explain your choice using structures to support your answer. Mere-eries-cecleone) The tran-i-browse-3-methylcyclohexionearrow_forwardPlease help me calculate the undiluted samples ppm concentration. My calculations were 280.11 ppm. Please see if I did my math correctly using the following standard curve. Link: https://mnscu-my.sharepoint.com/:x:/g/personal/vi2163ss_go_minnstate_edu/EVSJL_W0qrxMkUjK2J3xMUEBHDu0UM1vPKQ-bc9HTcYXDQ?e=hVuPC4arrow_forwardProvide an IUPAC name for each of the compounds shown. (Specify (E)/(Z) stereochemistry, if relevant, for straight chain alkenes only. Pay attention to commas, dashes, etc.) H₁₂C C(CH3)3 C=C H3C CH3 CH3CH2CH CI CH3 Submit Answer Retry Entire Group 2 more group attempts remaining Previous Nextarrow_forward
- Arrange the following compounds / ions in increasing nucleophilicity (least to most nucleophilic) CH3NH2 CH3C=C: CH3COO 1 2 3 5 Multiple Choice 1 point 1, 2, 3 2, 1, 3 3, 1, 2 2, 3, 1 The other answers are not correct 0000arrow_forwardcurved arrows are used to illustrate the flow of electrons. using the provided starting and product structures, draw the cured electron-pushing arrows for thw following reaction or mechanistic steps. be sure to account for all bond-breaking and bond making stepsarrow_forwardUsing the graphs could you help me explain the answers. I assumed that both graphs are proportional to the inverse of time, I think. Could you please help me.arrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY





