Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 10, Problem 10.16P
Interpretation Introduction
Interpretation: The reason as to why
Concept introduction: According to Hammond’s postulate, the structure of transition state resembles with the structure of compound that has energy near to it.
Electrophilic addition reactions are those in which breaking of pi bond take place to form new sigma bond. In this type of reaction, carbocation is formed during the formation of new bond.
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Explain the different products of the following two reactions by considering the mechanism by which each
reaction proceeds. As part of your explanation, use the curved arrow formalism to draw a mechanism for each
reaction.
CH,OH
CH2=CH-CH-CH, + Na*¯OCH,
CH;=CH-CH-CH3
Br
OCH,
CH,=CH-CH-CH, + CH,OH – CH,=CH–CH–CH, + CH,CH=CHCH,
Br
OCH,
OCH,
Why is the boiling point of propane-1,3-diol (HOCH2CH2CH2OH) higher than the boiling point of propane-1,2-diol [HOCH2CH(OH)CH3] (215 °C vs. 187 °C)? Why do both diols have a higher boiling point than butan-1-ol (CH3CH2CH2CH2OH, 118 °C)?
10) For the reaction between isopropyl 1-propyl (or 'n-propyl') ether and HBr, which type of reaction best
matches the expected products?
A) Acid-catalyzed dehydration
B) Nucleophilic substitution reaction
C) Ether cleavage reaction
D) Nucleophilic addition-elimination reaction
Chapter 10 Solutions
Organic Chemistry
Ch. 10 - Prob. 10.1PCh. 10 - Problem 10.2 How many degrees of unsaturation are...Ch. 10 - Give an example of a compound with molecular...Ch. 10 - Give the IUPAC name for each alkene.Ch. 10 - Give the IUPAC name for each polyfunctional...Ch. 10 - Prob. 10.6PCh. 10 - Prob. 10.7PCh. 10 - Prob. 10.8PCh. 10 - Prob. 10.9PCh. 10 - Problem 10.10 Rank the following isomers in order...
Ch. 10 - Linolenic acidTable 10.2 and stearidonic acid are...Ch. 10 - Prob. 10.12PCh. 10 - Prob. 10.13PCh. 10 - Prob. 10.14PCh. 10 - Prob. 10.15PCh. 10 - Prob. 10.16PCh. 10 - Prob. 10.17PCh. 10 - Prob. 10.18PCh. 10 - Prob. 10.19PCh. 10 - Which compounds A-D in Figure 10.12 are formed by...Ch. 10 - What two alkenes give rise to each alcohol as the...Ch. 10 - Prob. 10.22PCh. 10 - Problem 10.23 Draw the products of each reaction,...Ch. 10 - Problem 10.24 Draw all stereoisomers formed in...Ch. 10 - Prob. 10.25PCh. 10 - Prob. 10.26PCh. 10 - Borane is sold for laboratory use as a complex...Ch. 10 - What alkylborane is formed from hydroboration of...Ch. 10 - Draw the products formed when each alkene is...Ch. 10 - What alkene can be used to prepare each alcohol as...Ch. 10 - Prob. 10.31PCh. 10 - Draw the products of each reaction using the two...Ch. 10 - Problem 10.31 Devise a synthesis of each compound...Ch. 10 - Give the IUPAC name for each compound. a.b.Ch. 10 - a Label the carbon-carbon double bond in A as E or...Ch. 10 - Prob. 10.36PCh. 10 - Calculate the number of degrees of unsaturation f...Ch. 10 - Prob. 10.38PCh. 10 - The fertility drug clomiphene trade name Clomid is...Ch. 10 - Give the IUPAC name for each compound. a....Ch. 10 - Give the structure corresponding to each name. a....Ch. 10 - 10.40 (a) Draw all possible stereoisomers of, and...Ch. 10 - Prob. 10.43PCh. 10 - 10.42 Now that you have learned how to name...Ch. 10 - Prob. 10.45PCh. 10 - Prob. 10.46PCh. 10 - Prob. 10.47PCh. 10 - Prob. 10.48PCh. 10 - By using the bond dissociation energies in...Ch. 10 - Prob. 10.50PCh. 10 - Repeat Problem 10.50 with CH32C=CH2 as the...Ch. 10 - What alkene can be used to prepare each alkyl...Ch. 10 - Prob. 10.53PCh. 10 - Draw the constitutional isomer formed in each...Ch. 10 - Prob. 10.55PCh. 10 - Draw all stereoisomers formed in each reaction....Ch. 10 - Prob. 10.57PCh. 10 - Prob. 10.58PCh. 10 - Prob. 10.59PCh. 10 - Draw a stepwise mechanism for the following...Ch. 10 - Draw a stepwise mechanism for each reaction. a.b.Ch. 10 - Draw a stepwise mechanism that shows how all three...Ch. 10 - Less stable alkenes can be isomerized to more...Ch. 10 - Prob. 10.64PCh. 10 - Prob. 10.65PCh. 10 - Bromoetherification, the addition of the elements...Ch. 10 - Devise a synthesis of each product from the given...Ch. 10 - Prob. 10.68PCh. 10 - Prob. 10.69PCh. 10 - Prob. 10.70PCh. 10 - 10.66 Explain why A is a stable compound but B is...Ch. 10 - Prob. 10.72PCh. 10 - Prob. 10.73PCh. 10 - 10.69 Lactones, cyclic esters such as compound A,...Ch. 10 - 10.70 Draw a stepwise mechanism for the following...Ch. 10 - 10.71 Like other electrophiles, carbocations add...Ch. 10 - 10.72 Draw a stepwise mechanism for the...
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- Explain why methyl trifluoroacetate, CF3CO2CH3, is more reactive than methyl acetate, CH3CO2CH3, in nucleophilic acyl substitution reactions.arrow_forwardDraw the alkene that would react with the reagent given to account for the product formed. CH3 HCI CH3 CHCCH, ? + Či CH3 You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one.arrow_forwardBr2 in CCl4arrow_forward
- Why is benzene less reactive toward electrophiles than an alkene, even though it has more π electrons than an alkene (six versus two)?arrow_forwardWhen 2-chloropropane treated with NaOH and 1-chloropropane treated with NaOH separately produce two different functional groups. Provide both reactions and explain the two different functional groups produced.arrow_forward12) Use the curved arrow formalism to show the movement of electron pairs in the following reaction and label each reactant as a nucleophile or an electrophile. CHÍNH CHỊCH, + CO Học Nha CH₂CH₂CIarrow_forward
- Ethylene oxide reacts readily with HO- because of the strain in the three-membered ring. Explain why cyclopropane, a compound with approximately the same amount of strain, does not react with HO-.arrow_forwardB-Instructions: What reagent and/or catalysts are necessary to bring about each conversion? Br 1. CH-CH=CH-CH3 + CH;-CH CH-CH, CH CH 2. CH3-C=CH2 CH,C CH, HO. 3. CH, CH; 4. CH, C=CH, + CH, - C - CH, Br Brarrow_forwardGive IUPAC names for the following compounds: 1st structure: 2nd structure: SCH(CH3)2 || CH3CHCH₂CNHCH3 HCH₂CNHC Brarrow_forward
- Explain the apparent paradox. Although the addition of one equivalent of HX to an alkyne is more exothermic than the addition of HX to an alkene, an alkene reacts faster with HX.arrow_forwardComplete the following reaction by drawing a structural formula for the product. CH,CH, (1) NABH4 ? (2) H30* • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms.arrow_forwardIndicate which products A and B are. CH3-S-CH3 A + H3C- NaH A CH3 B H3C CH3arrow_forward
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