a)
Interpretation:
The product formed when 5-decyne reacts with H2 in the presence of Lindlar catalyst.
Concept introduction:
To predict:
The product formed when 5-decyne reacts with H2 in the presence of Lindlar catalyst.
Answer to Problem 32AP
The product formed when 5-decyne reacts with H2 in the presence of Lindlar catalyst is cis-5-decene
Explanation of Solution
When 5-decyne reacts with hydrogen in the presence of Lindlar catalyst, the addition of hydrogens to both carbons in triple bond takes place resulting in the formation of cis-5-decene.
The product expected when 5-decyne reacts with H2 in the presence of Lindlar catalyst is cis-5-decene.
b)
Interpretation:
The product formed when 5-decyne reacts with Li in ammonia.
Concept introduction:
Alkynes can be reduced by treatment with hydrogen in the presence of a catalyst. The hydrogenation occurs with anti stereochemistry to give a trans-alkene as product if Li in ammonia is used.
To predict:
The product formed when 5-decyne reacts with Li in ammonia.
Answer to Problem 32AP
The product formed when 5-decyne reacts with Li in ammonia is trans-5-decene.
Explanation of Solution
When 5-decyne reacts with hydrogen in the presence of Li in ammonia, the addition of hydrogens to both carbons in triple bond takes place following antistereochemistry resulting in the formation of trans-5-decene.
The product expected when 5-decyne reacts with Li in ammonia is trans-5-decene.
c)
Interpretation:
The product formed when 5-decyne reacts with one equivalent of bromine.
Concept introduction:
Alkynes undergo addition reactions with anti stereochemistry when treated with bromine. When treated with one equivalent of bromine a trans-dibromoalkene results as product by the addition of bromine atoms to the carbons in triple bond from opposite faces.
To predict:
The product formed when 5-decyne reacts with one equivalent of bromine.
Answer to Problem 32AP
The product formed when 5-decyne reacts with one equivalent of bromine is trans-5,6-dibromo-5-hexene.
Explanation of Solution
When 5-decyne reacts with bromine, the addition of bromine to both carbons in triple bond takes place following anti stereochemistry, resulting in the formation of trans-5,6-dibromo-5-decene as the product.
The product formed when 5-decyne reacts with one equivalent of bromine is trans-5,6-dibromo-5-decene.
d)
Interpretation:
The product formed when 5-decyne reacts with BH3 in THF followed by with H2O2, OH-.
Concept introduction:
Alkynes get hydrated in the hydroboration oxidation reaction. The reaction occurs with syn stereochemistry following anti Markovnikov regiochemistry to produce an enol. The enol then tautomerizes to yield a
To predict:
The product formed when 5-decyne reacts with BH3 in THF followed by with H2O2, OH-.
Answer to Problem 32AP
The product formed when 5-decyne reacts with BH3 in THF followed by with H2O2, OH- is 6-decanone.
Explanation of Solution
When 5-decyne is treated with BH3 in THF followed by with H2O2, OH-, the reaction occurs with syn stereochemistry following anti Markovnikov regiochemistry to produce an enol. The enol then tautomerizes to yield a ketone as the product. The Boron and hence the OH group adds to the less highly substituted carbon in triple bond and H adds to the more highly substituted carbon atom in the triple bond to produce an enol. The enol then tautomerizes to yield the ketone as the product.
The product formed when 5-decyne reacts with BH3 in THF followed by with H2O2, OH-is 6-decanone.
e)
Interpretation:
The product formed when 5-decyne reacts with H2O, H2SO4 in the presence of HgSO4 is to be given.
Concept introduction:
When treated with H2O, H2SO4 in the presence of HgSO4 alkynes get hydrated to produce enols. The addition of water to unsymmetrical alkynes follows Markonikov regiochemistry while it cannot be applied in the case of symmetrical alkynes. The enols produced then undergo tautomerization to give a ketone as the product.
To predict:
The product formed when 5-decyne reacts with H2O, H2SO4 in the presence of HgSO4.
Answer to Problem 32AP
The product formed when 5-decyne reacts with H2O, H2SO4 in the presence of HgSO4 is 5-decanone.
Explanation of Solution
5-Decyne is a symmetrical alkyne. Hence Markonikov regiochemistry is not applicable. When treated with dilute H2SO4 in the presence of HgSO4, the OH group adds to a carbon in triple bond and H adds to the other carbon in triple bond to yield an enol. The enol then tautomerizes to yield the ketone, 5-decanone.
The product formed when 5-decyne reacts with H2O, H2SO4 in the presence of HgSO4 is 5-decanone.
f)
Interpretation:
The product formed when 5-decyne reacts with excess H2 in the presence of Pd/C is to be given.
Concept introduction:
When treated with excess H2, Pd/C catalyst the alkynes react with two molar equivalents of hydrogen to give the parent
To predict:
The product formed when 5-decyne reacts with excess H2 in the presence of Pd/C.
Answer to Problem 32AP
The product formed when 5-decyne reacts with excess H2 in the presence of Pd/C is n-decane.
Explanation of Solution
When 5-Decyne is treated with excess H2 in the presence of Pd/C, two molar equivalents of hydrogens add to the triple bond. The corresponding alkane, n-decane is the product.
The product formed when 5-decyne reacts with excess H2 in the presence of Pd/C is n-decane.
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Chapter 9 Solutions
Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th
- Please draw by handarrow_forward3. Predict the major product and give a mechanism for the following reactions: (CH3)3COH/H₂SO4 a) b) NC CH₂O c) LOCH, (CH3)3COH/H2SO4 H,SO -OHarrow_forwardIndicate if the aldehyde shown reacts with the provided nucleophiles in acid or base conditions. a NaBH4 be Li eli -NH2 P(Ph3) f KCN g OH excess h CH3OH i NaCHCCH3arrow_forward
- Predict the major products of the following organic reaction: + A ? Some important notes: • Draw the major product, or products, of the reaction in the drawing area below. • If there aren't any products, because no reaction will take place, check the box below the drawing area instead. • Be sure to use wedge and dash bonds when necessary, for example to distinguish between major products that are enantiomers. Explanation Check Click and drag to start drawing a structure. C © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Centearrow_forwardPolar solutes are most likely to dissolve into _____, and _____ are most likely to dissolve into nonpolar solvents. A. nonpolar solutes; polar solvents B. nonpolar solvents; polar solvents C. polar solvents; nonpolar solutes D. polar solutes; nonpolar solventsarrow_forwardDeducing the Peactants Can the molecule on the right-hand side of this organic reaction be made in good yield from no more than two reactants, in one step, by moderately heating the reactants? ? Δ If your answer is yes, then draw the reactant or reactants in the drawing area below. You can draw the reactants in any arrangement you like. If your answer is no, check the box under the drawing area instead. Explanation Check Click and drag to start drawing a structure. © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center Xarrow_forward
- Draw all 8 stereoisomers, circling each pair of enantiomer(s)/ mirror image compound(s)arrow_forwardBookmarks Profiles Tab Window Help Chemical Formula - Aktiv Che X + → C 11 a app.aktiv.com Google Chrome isn't your default browser Set as default Question 12 of 16 Q Fri Feb 2 Verify it's you New Chrome availabl- Write the balanced molecular chemical equation for the reaction in aqueous solution for mercury(I) nitrate and chromium(VI) sulfate. If no reaction occurs, simply write only NR. Be sure to include the proper phases for all species within the reaction. 3 Hg(NO3)2(aq) + Cг2(SO4)3(aq) → 3 Hg₂SO (s) + 2 Cr(NO3), (aq) ean Ui mate co ence an climate bility inc ulnerabili women, main critic CLIMATE-INI ernational + 10 O 2 W FEB 1 + 4- 3- 2- 2 2 ( 3 4 NS 28 2 ty 56 + 2+ 3+ 4+ 7 8 9 0 5 (s) (1) Ch O 8 9 (g) (aq) Hg NR CI Cr x H₂O A 80 Q A DII A F2 F3 FA F5 F6 F7 F8 F9 #3 EA $ do 50 % 6 CO & 7 E R T Y U 8 ( 9 0 F10 34 F11 川 F12 Subr + delete 0 { P }arrow_forwardDeducing the reactants of a Diels-Alder reaction n the molecule on the right-hand side of this organic reaction be made in good yield from no more than two reactants, in one step, by moderately heating the reactants? ? Δ • If your answer is yes, then draw the reactant or reactants in the drawing area below. You can draw the reactants in any arrangement you like. • If your answer is no, check the box under the drawing area instead. Explanation Check Click and drag to start drawing a structure. >arrow_forward
- Predict the major products of the following organic reaction: + Some important notes: A ? • Draw the major product, or products, of the reaction in the drawing area below. • If there aren't any products, because no reaction will take place, check the box below the drawing area instead. • Be sure to use wedge and dash bonds when necessary, for example to distinguish between major products that are enantiomers. Explanation Check Click and drag to start drawing a structure.arrow_forwardif the answer is no reaction than state that and please hand draw!arrow_forward"I have written solutions in text form, but I need experts to rewrite them in handwriting from A to Z, exactly as I have written, without any changes."arrow_forward
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