/*! This file is auto-generated */ .wp-block-button__link{color:#fff;background-color:#32373c;border-radius:9999px;box-shadow:none;text-decoration:none;padding:calc(.667em + 2px) calc(1.333em + 2px);font-size:1.125em}.wp-block-file__button{background:#32373c;color:#fff;text-decoration:none} Q38P Predict the products of the foll... [FREE SOLUTION] | 91Ó°ÊÓ

91Ó°ÊÓ

Predict the products of the following reactions:

(a) ±ð³æ³¦±ð²õ²õ â¶Ä‰N±á3 â¶Ä‰+ â¶Ä‰Ph−CH2CH2CH2Br→

(b)1−bromopentane→(2)LiAlH4(3)H3O+(1)NaN3

(c)

(d) product â¶Ä‰from â¶Ä‰part â¶Ä‰c→heat

(e)

(f) product â¶Ä‰from â¶Ä‰part â¶Ä‰e→(3)heat(1)excessCH3I(2)Ag2O

(g)

(h)

(i)

(j) product â¶Ä‰from â¶Ä‰part â¶Ä‰i→(2)H3O+(1)LiAlH4

(k)

(l)

Short Answer

Expert verified

(a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)

(i)

(j)

(k)

(l)

Step by step solution

01

Prediction of products

(a) (3-bromopropyl)benzene on treatment with excess ammonia gives the product as 3-phenylpropan-1-amine.

reaction a

(b) 1-bromopentane on treatment with sodium azide forms 1-azidopentane, which on further reduction with lithium aluminum hydride gives the final product as pentan-1-amine.

reaction b

(c) 1-methylpiperidine reacts with hydrogen peroxide to give the product as 1-methylpiperidine 1-oxide.

reaction c

(d) 1-methylpiperidine 1-oxide on heating gives the product as N-methyl-N-(pent-4-en-1-yl)hydroxylamine.

reaction d

(e) Octahydro-1H-quinolizine on treatment with excess methyl iodide gives the initial product as 5-methyldecahydroquinolizin-5-ium, which on further reaction with silver oxide followed by heating gives the final product as 2-(but-3-en-1-yl)-1-methylpiperidine.

reaction e

(f) 2-(but-3-en-1-yl)-1-methylpiperidine on treatment with excess methyl iodide gives the initial product as 2-(but-3-en-1-yl)-1,1-dimethylpiperidin-1-ium, which on further reaction with silver oxide followed by heating gives the final product as N,N-dimethylnona-1,8-dien-5-amine.


reaction f

(g) Piperidine on treatment with sodium nitrite in presence of hydrochloric acid gives the product as 1-nitrosopiperidine.

reaction g

(h) Nitrobenzene on treatment with zinc in presence of hydrochloric acid gives the product as aniline.

reaction h

(i) 2-cyclohexylacetyl chloride on treatment with methylamine in presence of pyridine gives the product as 2-cyclohexyl-N-methylacetamide.

reaction i

(j) 2-cyclohexyl-N-methylacetamide on reduction with lithium aluminum hydride gives the final product as 2-cyclohexyl-N-methylethanamine.

reaction j

(k) (E)-N-(heptan-3-ylidene)methanamine on reduction with lithium aluminum hydride gives the final product as N-methylheptan-3-amine.

reaction k

(l) 2-methyl-3-phenylpropanenitrile on reduction with lithium aluminum hydride gives the final product as 2-methyl-3-phenylpropan-1-amine.

reaction l

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Over 30 million students worldwide already upgrade their learning with 91Ó°ÊÓ!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

The two most general amine syntheses are the reductive amination of carbonyl compounds and the reduction of amides. Show how these techniques can be used to accomplish the following syntheses.

(a) benzoic acid to benzylamine

(b) benzaldehyde to benzylamine

(c) pyrrolidine to N-ethylpyrrolidine

(d) cyclohexanone to N- cyclohexylpyrrolidine

(e) HOOC-(CH2)3 -COOH to pentane-1,5-diamine cadaverine

(A true story.) A drug user responded to an ad placed by a DEA informant in a drug-culture magazine. He later flew from Colorado to Maryland, where he bought some 1-phenyl-2-propanone (P2P) from the informant. The police waited nearly a month for the suspect to synthesize something, then obtained a search warrant, and searched the residence. They found the unopened bottle of P2P; apparently, the suspect was not a good chemist and was unable to follow the instructions the informant gave him. They also found pipes and bongs with residues of marijuana and cocaine, plus a bottle of methylamine hydrochloride, some muriatic acid (dilute HCL), zinc strips, flasks, and other equipment.

(a) Assume you are consulting for the police. Show what synthesis the suspect was prepared to carry out, to provide probable cause for the charge of attempting to manufacture a controlled substance.

(b) Assume you are a member of the jury. Would you convict the defendant of attempting to manufacture a controlled substance?

Propose a mechanism for nitration of pyridine at the 4-position, and show why this orientation is not observed.

Show how you would use the same sulfonyl chloride as used in the sulfanilamide synthesis to make sulfathiazole and sulfapyridine.

Question. Propose a mechanism for the sulfonation of pyridine, and point out why sulfonation occurs at 3-position.

See all solutions

Recommended explanations on Chemistry Textbooks

View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.