/*! 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} Q16P Show how you would accomplish th... [FREE SOLUTION] | 91Ó°ÊÓ

91Ó°ÊÓ

Show how you would accomplish the following synthesis.

(a) Acetphenone→ acetophenone cyanohydrin

(b) Cyclopentancarbaldehyde→ 2-cyclopentyl-2-hydroxyacetic acid

(c) Hexan-1-ol →2-hydroxyheptanoic acid

Short Answer

Expert verified

Acetophenone on reaction with hydrogen cyanide undergoes nucleophilic addition reaction. Cyanide ion acts as a nucleophile and attacks at the carbonyl carbon which is electrophilic in nature and we get acetophenone cyanohydrin as the product.

Acetophenone Acetophenone cyanohydrin

Step by step solution

01

Explanation of part (a):

Acetophenone on reaction with hydrogen cyanide undergoes nucleophilic addition reaction. Cyanide ion acts as a nucleophile and attacks at the carbonyl carbon which is electrophilic in nature and we get acetophenone cyanohydrin as the product.

Acetophenone Acetophenone cyanohydrin

02

Explanation of part (b):

Cyclopentancarbaldehyde on reaction with hydrogen cyanide undergoes nucleophilic addition reaction of cyanide ion onto the carbonyl carbon of aldehyde. Cyanohydrin gets formed which on hydrolysis yields 2-cyclopentyl-2-hydroxyacetic acid. Cyano group gets converted to acid functional group on hydrolysis.

2-cyclopentyl-2- hydroxyacetic acid

03

Explanation of part (c):

Hexan-1-ol on treatment with PCC which is an oxidizing agent, gets converted to hexanal. PCC oxidises alcoholic functional group to aldehyde. On addition of hydrogen cyanide in next step, hexanal undergoes nucleophilic addition reaction of cyanide ion onto carbonyl carbon of aldehyde which leads to generation of cyanohydrin and further hydrolysis yields required product, that is, 2-hydroxyheptanoic acid.

2-hydroxyheptanoic acid

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

Question. (a) Simple aminoacetals hydrolyze quickly and easily in dilute acid. Propose a mechanism for hydrolysis of the following aminoacetal:

(b) The nucleosides that make up DNA have heterocyclic rings linked to deoxyribose by an aminoacetal functional group. Point out the aminoacetal linkages in deoxycytidine and deoxyadenosine.

(c) The stability of our genetic code depends on the stability of DNA. We are fortunate that the aminoacetal linkages of DNA are not easily cleaved. Show why your mechanism for part (a) does not work so well with deoxycytidine and deoxyadenosine.

Rank the following carbonyl compounds in order of increasing equilibrium constant for hydration:

CH3COCH2Br BrCH2CHO      CH2O      CH3COCH3      CH3CHO


Question: The family of macrolide antibiotics all have large rings (macrocycle) in which an ester is what makes the ring; a cyclic ester is termed as a lactone. One example is amphotericin B, used as an anti-fungal treatment of last resort because of its liver and heart toxicity. Professor Martin Burke of the University of Illnois has been making analogs to retain the antifungal properties but without the toxicity, including this structure published in 2015. (Nature Chemical Biology, (2015) doi: 10.1038/nchembio.1821). The carboxylate of amphotericin B has been replaced with the urea group (shown in red).

(a) Where is the lactone group that forms the ring?

(b) Two groups are circled. What type of functional group are they? Explain.

Show how you would accomplish the following syntheses efficiently and in good yield. You may use any necessary reagents.

(a)acetaldehyde→lacticacid,CH3CH(OH)COOH

(b)

(c)

(d)

(e)

(f)

(g)

Use equations to show the fragmentation leading to each numbered peak in the mass spectrum of octane-2-one .

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.