ANSWER ALL QUESTIONS ONLY - NO EXPLANATION NEEDED

xoxbmrxox

Main

Home >Homework Answsers >Chemistry homework help >Organic chemistry homework help

a year ago
24.04.2025
100

Report issue

files (1)

Practice.docx

Practice.docx

IR Correlation Table

C-H Alkanes (stretch) 3000-2850 s

-CH3 (bend) 1450 & 1375 m

-CH2 (bend) 1465 m

Alkenes (stretch) 3100-3000 m

(out-of-plane) 1000-650 s

Aromatics (stretch) 3150-3050 s

(out-of-plane) 900-690 s

Alkyne (stretch) ~3300 s

Aldehyde 2900-2700 w

C=C Alkene 1680-1600 m-w

Aromatic 1600 & 1475 m, w

C≡C Alkyne 2250-2100 m-w

C=O Carbonyl 1780-1680 s

C-O ROH,ROR,ROOH,ROOR 1300-1000 s

O-H Alcohol, carboxylic acid 3600-3200 m

N-H (stretch) 3500-3100 m

(bend) 1640-1550 m-s

C-N Amines 1350-1000 m-s

C-X Alkyl Halide 600-900 w

HDI

1. Answer the questions below (2 each)- note these are all independent questions

Name:

(a) label the defined stereocenter as R or S isomer – show your work for credit!

(b) draw a conjugate acid-base pair

(d) draw the major product of monochlorination of the molecule below

(e) draw an aromatic hydrocarbon which is NOT benzene

(f) identify the functional groups present in the molecule

(g) draw a hydrocarbon structure which would exhibit a signal at 3300 cm-1 in its IR spectrum

(h) provide a structure which fits the following terms:

(i) β-keto ester (ii) 3° alcohol

(iii) enamine (iv) bulky base/base only reagent

(v) anti Newman projection (vi) reducing reagent

(vii) cuprate reagent (viii) allylic carbocation

(i) Name or draw the following organic molecules

(i) (ii) 2,3-diethyl-4-methylcyclohexanone

(iii) butyl methyl ether (iv)

(v) 3-chloroaniline (vi)

(j) draw a 6 carbon non-conjugated diene

(k) circle a sp3 atom and square a sp atom in the molecule below

(l) draw a molecule with formula C4H11N which exhibits hydrogen bonding with water but not itself

2. Fill in the boxes below with the correct reagent, reactant or product(s). Show the correct

stereochemistry for products which require it (36)

(a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)

(i)

(j)

(k)

(l)

(m)

(n)

(o)

(p)

(q)

(r)

3. Use priority rules to label the alkenes below as either the E or Z conformer- show your work for credit!

(8)

(a) (b)

stereochemistry in product)

4. A molecule has been identified and the structure is shown below. Also supplied is the IR and H NMR

spectrum. Use these spectra to confirm the identity of the molecule as directed (17)

(a) identify the bond represented by the labeled peaks in the IR, list

these bonds with the spectra’s label (ex. Peak 1 = C-C)

Bonds from IR:

(b) for the labels on the H NMR below provide: (1) calculated integration value, (2) splitting pattern

and (3) the structural piece the signal represents (ex. B: 3H, t is a CH3-CH2 piece)

IR or the NMR spectra

Other proposed structure:

5. Draw an arrow-pushing mechanism to explain the following conversions. Show all intermediate

structures and watch your arrows and charges (17)

(a)

(b)

(c)

(d)

(e)

6. Design a synthesis to make the following molecule starting from the indicated starting material.

Show the intermediate structure after each alteration (5)

7. Fill in the boxes below with the correct reagent or product (6)

(a)

(b)

(c)

8. Provide the mechanism for the formation of the benzene derivative shown. Remember to include the

step(s) to form the electrophile (4)

Scrap Paper

image4.emf

image5.emf

image6.emf

image7.emf

image8.emf

image9.emf

image10.emf

image11.emf

image12.emf

image13.emf

image14.emf

image15.emf

image16.emf

image17.emf

image18.emf

image19.emf

image20.emf

image21.emf

image22.emf

image23.emf

image1.jpeg

image24.emf

image25.emf

image26.emf

image27.emf

image28.emf

image2.emf

image29.jpeg

image290.jpeg

image30.emf

image31.jpeg

image32.emf

image33.emf

image34.emf

image35.emf

image36.emf

image37.emf

image38.emf

image3.emf

image39.emf

image40.emf

image41.emf

image42.emf