Loading...

Messages

Proposals

Stuck in your homework and missing deadline? Get urgent help in $10/Page with 24 hours deadline

Get Urgent Writing Help In Your Essays, Assignments, Homeworks, Dissertation, Thesis Or Coursework & Achieve A+ Grades.

Privacy Guaranteed - 100% Plagiarism Free Writing - Free Turnitin Report - Professional And Experienced Writers - 24/7 Online Support

Borneol nmr

08/01/2021 Client: saad24vbs Deadline: 3 days

REDUCTION OF A KETONE


OBJECTIVES: To perform a reduction of a ketone functional group suing NaBH4. To identify the isomer obtained by NMR.


Background


Reduction of carbonyl groups.


NaBH4 and LiAlH4 are common reagents utilized for reduction of ketones and aldehydes. They are called “metal hydrides” and they eract delivering an hydride (H-). In reactions with ketones and aldehyde they can be used interchangeably (unless there are other functional groups that could potentially react too). NaBH4 is considered a “milder” reducing agent, while LiAlH4 is considered “stronger”. For instance, esters, carboxylic acids can be reduced only using LiAlH4. Creation of a new stereogenic center upon reduction of an achiral ketone is expected to result in a racemic mixture of enantiomers that are indistinguishable by NMR.


Reduction of camphor


However, camphor is chiral. One side of the bicyclic ring is much more sterically hindered than the other side, making it possible for an achiral reducing agent such as NaBH4 to be selective for one


isomer. You will determine the isomers using NMR. Both isoborneol and borneol are obtained from reduction. The dominant isomer can be predicted based on the mechanism of the reaction, and the ratio of these isomers can be determined experimentally by NMR analysis. 3 As in the case of camphor, the NMR spectra are quite complicated. However, the proton adjacent to the alcohol in both compounds appears in a clear region of the 1H NMR spectrum that can be integrated to find the isomer ratio.


Distinguishing Borneol and Isoborneol Using NMR


You are given a 1H-NMR spectrum of borneol as a reference. Obtain 1H NMR spectra of the product mixture from Procedure B. In the 1H NMR, look closely at the protons on the alcohol carbon. (Hint: these typically appear at 3.5-4.0 ppm). The ratio of these groups of peaks corresponds to the percentages of isoborneol and borneol. In Delta, use integration to determine the relative amounts of the two products. You should use the zoom tool to expand the region, then integrate the CHOH signals; use the "cut integral" tool to separate the integrals so that you can calculate a ratio. The easiest way to do this is to select the smaller one (so it is yellow), and type "1".


Experimental


Start with 500 mg of camphor. Dissolve in methanol in an Erlenmeyer flask to make a 1.15 M solution. Cool the solution on an ice bath, then add 1 molar equivalent of NaBH4 in three portions over 10 min,


see below. After all of the sodium borohydride is added, boil the mixture on a sand bath (hotplate) for 2 minutes. Pour the product mixture into ice and rinse the flask with ~1.25 mL of methanol into the ice. Collect the white precipitate on a Hirsch funnel. Dissolve the solid in about 5-8 mL of ether in small erlenmeyer, dry with CaCl2, transfer


to a tared round-bottom flask, then remove the ether using a rotary evaporator. Calculate a percent yield of the crude dry product. Take


an 1H NMR spectrum of the product to determine purity and identify products


References


1. Based on a microscale experiment on the oxidation of 9- fluorenol to 9-fluorenone. Jones, C. S.; Albizati, K. J. Chem. Educ. 1994, 71, A271-A272.


2. Based on a microscale experiment on the reduction of camphor to isoborneol Pavia, Lampman, Kris Advanced Organic Laboratory, 3rd ed. Saunders: New York, 1985.


2


POST LAB


1) Write the introduction for the reduction experiment in not more than 5 sentences


2) Write the abstract using not more than 4 sentences


3) Write a short discussion (include the following points: 1) mechanism of the reaction, 2) which isomer is formed in higher yield based on the NMR analysis, 3) Discuss the NMR and how it helps in evaluating the final product


3) Write the experimental section (NMR analysis


using the following format (Ex: 1H-NMR (CDCl3)


δ1.2 (t, 2H, J = 6.1Hz), 1.8 (s, 9H), 2.0 (s,


3H), 2.3 (t, 2H, J= 6Hz).


4) Write the conclusions section.

Homework is Completed By:

Writer Writer Name Amount Client Comments & Rating
Instant Homework Helper

ONLINE

Instant Homework Helper

$36

She helped me in last minute in a very reasonable price. She is a lifesaver, I got A+ grade in my homework, I will surely hire her again for my next assignments, Thumbs Up!

Order & Get This Solution Within 3 Hours in $25/Page

Custom Original Solution And Get A+ Grades

  • 100% Plagiarism Free
  • Proper APA/MLA/Harvard Referencing
  • Delivery in 3 Hours After Placing Order
  • Free Turnitin Report
  • Unlimited Revisions
  • Privacy Guaranteed

Order & Get This Solution Within 6 Hours in $20/Page

Custom Original Solution And Get A+ Grades

  • 100% Plagiarism Free
  • Proper APA/MLA/Harvard Referencing
  • Delivery in 6 Hours After Placing Order
  • Free Turnitin Report
  • Unlimited Revisions
  • Privacy Guaranteed

Order & Get This Solution Within 12 Hours in $15/Page

Custom Original Solution And Get A+ Grades

  • 100% Plagiarism Free
  • Proper APA/MLA/Harvard Referencing
  • Delivery in 12 Hours After Placing Order
  • Free Turnitin Report
  • Unlimited Revisions
  • Privacy Guaranteed

6 writers have sent their proposals to do this homework:

University Coursework Help
Top Essay Tutor
Helping Hand
Writer Writer Name Offer Chat
University Coursework Help

ONLINE

University Coursework Help

Hi dear, I am ready to do your homework in a reasonable price.

$62 Chat With Writer
Top Essay Tutor

ONLINE

Top Essay Tutor

I have more than 12 years of experience in managing online classes, exams, and quizzes on different websites like; Connect, McGraw-Hill, and Blackboard. I always provide a guarantee to my clients for their grades.

$65 Chat With Writer
Helping Hand

ONLINE

Helping Hand

I am an Academic writer with 10 years of experience. As an Academic writer, my aim is to generate unique content without Plagiarism as per the client’s requirements.

$60 Chat With Writer

Let our expert academic writers to help you in achieving a+ grades in your homework, assignment, quiz or exam.

Similar Homework Questions

Persuasive Instructions - Unfiltered society treats sex workers as second class citizens - Chapter 10 kernel color in corn answers - Solving a 2x2 system of linear equations - Biochemical engineering an introductory textbook - Hunches that communication theory are built about should be - Triangular prism edges faces vertices - DNP - Business Process Redesign - Mays and mccovey are beer brewing companies - Spanish homework help - Chicago title insurance company canada - Crainer crazy craft 2.0 ep 15 - Who invented homework and why - What are the three sources of a unique and valuable strategic position? - Wrexham borough council planning - Comnet switch default ip - Kfc rules and regulations - History discussion - Cafs hsc past papers - CARIBBEAN RELIGION HISTORY - Ati system disorder template pdf - The orbit of mercury lab answers - Are all producers autotrophs - BQM Case Study Analysis - American dream final project - Critical evaluation essay example - Analysis of economic data 4th edition pdf - Strategic Plan Outline - Encase forensic v7 user guide - Smart goal on Opioid crisis of California - Acs code of professional conduct assignment - Running record conversion chart - Joint commission soiled utility room - Poli 30d - Moodle blackpool and fylde - Infinite monkeys app builder - Srs document example for airline reservation system - Mat 540 week 8 assignment 1 - The chocolate war setting - Bell jar experiment to show transpiration - Red hill greek church easter - Cooking meats activity d chapter 18 answers - Discussion: Does money really make the world go 'round? - What is character construction - Rewrite without parentheses and simplify - Coburg north primary school rating - Starbucks in japan case study - Stobhill hospital phone number - Prudential prufund growth fund - Uniform bank holding company performance report - Invictus tea scene - Six kingdoms of life characteristics - ETCM DISCUSSION-2 - Ustedes van a levantarse temprano. - Animal testing persuasive speech outline - Apple subscription accounting - Why did the zoot suit riots happen - How do you make a genogram - Ethical - Agile documentation and planning template - Condensation is a warming process because - National communication association credo for ethical communication - Case study treatment plan - Evaluating instructional materials checklist - A computer system consists of - Professional presentation - Matcam oz pty ltd - Sample persuasive speech outline on volunteering - Submission identifying your thesis - Environmental science crossword puzzle answer key - Tesla code of conduct - Discussion: Politics and the Patient Protection and Affordable Care Act - George mason guaranteed admission nova - Strategic ANALYSIS OF A PUBLIC COPORATION - Jaya wahi healing centre - Nordstrom market segmentation - Shakespeare by matthew arnold theme - Ikea invades america harvard case study - 2 dimensional design projects - Electrical current in a metal wire involves the flow of - Essay Affirmative Action - Lgcc mountain view - News reflection: Cyber Security, Privacy or Ethics - 2 traits that represent a non sustainable society - Hei spark tester napa - Active directory topology diagrammer windows server 2012 r2 - Anthem for doomed youth sonnet - Are you smarter than a monkey - Why study psychology worksheet answers - Risk management dashboard examples - 291 boardman road kingaroy - Gmc medical licensing assessment - Catholic apostolic succession chart - Research Proposal 1.0 - The hart celler act of 1965 quizlet - What is an epiphany moment - NEED IN 12 HOURS or LESS - Reaction paper 2 - Vaccines social media and the public health answer key